Explore Top-Rated Chalets in Weymouth, UK

Chickerell View Aspen is situated in Wyke Regis. This chalet offers a terrace. The chalet comes with 2 bedrooms, a flat-screen TV and a fully equipped kitchen that provides guests with an oven and a microwave. Weymouth is 3.7 km from the chalet. The nearest airport is Bournemouth Airport, 62 km from the property.

Parking • Kitchen • Child Friendly • Laundry • Breakfast • Smoking • Pool • Private Pool • Balcony/Terrace

Set in Wyke Regis, just 1.1 km from Chesil Beach, Littlesea Reeds holiday home offers accommodation with a garden, a terrace, a restaurant and free WiFi. Situated 27 km from Monkey World, the property features a bar and free private parking. The chalet with a patio and sea views features 3 bedrooms, a living room, a flat-screen TV, an equipped kitchen with a fridge and an oven, and 2 bathrooms with a shower. A children's playground is available for guests to use at the chalet. Golden Cap is 34 km from Littlesea Reeds holiday home, while Corfe Castle is 41 km away. The nearest airport is Bournemouth Airport, 61 km from the accommodation.

Pet Friendly • Breakfast • Balcony/Terrace • Smoking • Private Pool • Child Friendly • Parking • Pool • Internet

With Chesil Beach reachable in a 9-minute walk, Fleet View provides accommodations, a restaurant, a seasonal outdoor swimming pool, a garden, and a bar. Guests can benefit from a balcony and a children's playground. The chalet features parking on-site, an indoor pool, and full-day security. This 2-bedroom chalet comes with a seating area, a flat-screen TV, and a fully equipped kitchen with an oven. Guests can take in the views of the sea from the terrace, which also has outdoor furniture. The accommodation has a fireplace. A mini-market is available at the chalet. Weymouth Harbour is 2.9 miles from the chalet, while Monkey World is 17 miles from the property. Bournemouth Airport is 39 miles away.

- "It was a lovely experience staying in Fleet View. We really enjoyed our stay there and would definitely recommend this t" - "Last minute accommodation needed and they were able to accommodate us with a great property, clean, comfortable and grea"

Weymouth Bay is a family friendly holiday park. Our caravan is located in a quiet cul de sac a short walk from both the site facilities and the beach path. The caravan has small side veranda with a gate to stop little ones escaping. We have our own tarmac parking space next to the caravan.  There is also a lovely grass area with a picnic table to enjoy on sunny days.

The space
Three Comfy Bedrooms
There is one double bedroom and two twin rooms.  All the bedrooms are double glazed and have blown air heating so are cosy all season long. They also all have bedside tables, mirrors and wardrobes so plenty of storage space and room for home comforts. Duvets and pillow are provided.  Unfortunately we do not supply linen but this can be hired direct from Haven at a small charge.  You will need to provide your own towels and tea towel.

Living Room and Dining Area
The living room is lovely and spacious with plenty of sofa space for the whole family. There is a TV with freeview and integrated DVD player.  We have put a few DVDs and board games in the cupboard to keep the kids (and adults) amused in the evening or on rainy days. We have also provided leaflets and information about the local area so you can make the most of what the park and its surroundings have to offer. There is also a dining area so you can enjoy a nice home cooked meal or sample one of the local takeaways in comfort. The open plan living and dining area benefit from a gas fire and double glazing.

Kitchen
There is a kitchen with everything you might need to keep the family fed during your stay. There is an oven with grill, fridge/freezer, microwave and toaster. There is a full inventory of tableware including for children's items as well as a full range of cookware. There is plenty of storage space in the kitchen. We also regularly restock tea, coffee, sugar and basic cleaning items so although we can't guarantee it you should find some domestic items to get you started on arrival.

Shower Room
The caravan has a spacious shower room with basin and toilet. There is also plenty of room for the whole families toiletries. In additional there is a separate toilet and basin so no queueing for the loo.

Guest access
If you purchase Haven Play passes you will be able to access all the on site facilities which include:
Outdoor lazy river
Indoor pool
Children's adventure play area
Evening entertainment
Amusement area
Restaurant and bar.

Children’s books and toys • Clothing storage: closet • Hangers • Drying rack for clothing • Hair dryer • Children’s dinnerware • TV • Cleaning products • Hot water • Books and reading material

Lovely Caravan at Weymouth Bay Holiday Park on the Dorset coast. The caravan is located on a corner plot with its own private garden area with outdoor seating. 3 bedrooms and sleeps up to 6 people. 10 minutes walk to the beach.

The space
Located on Weymouth Bay Holiday Park owned by Haven, this large caravan is sited in a corner plot with outdoor seating (table and chairs, swing seat and two loungers) and within a short walk to the site facilities and Spar shop. A stream runs by the caravan.

There are three bedrooms set out as 1 double and two twin rooms, although one of the twin rooms can be made in to a double bed on request.

The caravan is fully furnished with its own fast wi-fi connection, DVD player and flat screen TV, electric heating in the bedrooms with gas fire in the lounge, shower room with toilet and a second separate toilet, gas cooker, fridge and microwave.
There is parking adjacent to the caravan, along with ample additional parking opposite.

The Haven Holiday Park facilities are accessed by purchase of a Site Facilities Pass which is bought directly from Haven Reception. This gives guests access to the following :
* Swimming Pool with Lazy River
* Daytime and evening entertainment

Other things to note
A key safe enables easy access for arrivals

Iron • TV • Heating • Hangers • Smoke alarm • Hot water • Hair dryer • Indoor fireplace • Carbon monoxide alarm • Essentials

3 bed static home in an elevated position on the beautifully kept Waterside Bowleaze Holiday Park on the Jurassic Coast!

Saturday checkins only during peak season.

1 double, 2 twins & sofabed.2 bathrooms,1 with shower.Large deck area with seating & sea views!Parking for 2 cars.

Facilities: spa/gym/restaurant/sports bar/soft-play/kids park/pool (indoor & outdoor). Prices include park passes!

Sorry no single sex groups or dogs.

For off peak bookings, contact us directly to discuss.

The space
Guests may enjoy the whole space plus the amazing Bowleaze Cove Holiday Park facilities (swimming passes are payable directly to the park reception on site). Park facilities such as sports bar/pool/spa are only available in peak seasons. Wifi is available in the accommodation and indoor areas of the resort.

The bedrooms are cosy and functional but not spacious, they are standard twin rooms and one double which you get in this type of property. Please see pictures. They do have ample storage space.

The lounge and kitchen are open plan and the deck has plenty of space and sea views.

Seating is inside and out for 4 however there are a few extra stools and rattan furniture you can utilise if needed.

There are neighbouring caravans either side so please do be respectful of our neighbours.

As stated elsewhere, bed linen and hand towels are provided but you will need to bring your own towels.

There is a vacuum available although we ask that guests please empty it after use to ensure it works for the next person.

Other things to note
Please liase with us directly regarding any issues as opposed to park reception staff as this is a private rental.

You will need to send us all names of your party so you can be given park passes on check in. Please also provide us with a contact phone number and car registration(s).

You will need to provide your own towels and tea towel. Cleaning products will be available plus a few dishwasher tablets.

Linen is provided but you will need to make up beds. Please only make up the number of beds you are using. On departure please leave all used bed linen in a black bag in the kitchen.

Please leave the property in the condition you find it as per Airbnb terms of service. Cleaning supplies will be available under the sink. Any used cleaning cloths can be left with your linen at the end of your stay. STRICTLY NO SMOKING.

Swimming is payable daily at £8.00 per adult and £6.00 per child per visit. You will need your own towels.

This holiday caravan is large enough for the whole family
Enough bedrooms for the larger families. At the end of the row of caravans,so not many people walking past.
Haven holiday parks are great for families, where entertainment passes can be purchased, through haven, but also good for people wanting a quiet stay.

The space
Well presented Swift Loire 3 bedroom caravan located on the popular Littlesea Holiday Park in Weymouth .

3 bed,rooms perfect for family holiday. Based at Littlesea Weymouth. Set in west acres
Based at the end of row. With a fence stream behind.
Safe for children as no cars driving past.
Parking for one car, please be mindful of other cars and not block the road.
Ramp to the door so great for limited mobility.
Has double glazing throughout.
Central heating
1 double bedroom with a TV
2 twin bedrooms
1 pull out sofa bed in lounge, not the most comfortable ( No more than 8 your booking could be cancelled by Haven if there is found to be more!!).

The caravan itself has a good size shower, fireplace in the lounge, central heating throughout, a good sized fridge freezer, microwave, television, WiFi, hairdryer, parking space next to the caravan for one car, other cars will have to park in any of the car parks.
The fully equipped kitchen is in the open plan living area, all you need is your own washing up liquid, bedding and tea towels etc.
Picnic table, at the front of the Caravan, can be used for sitting out and eating, or just a drink on an evening.

The Haven site benefits.
- Indoor and outdoor swimming pool with various sessions, and activities.
- Laundrette
-Pappa Johns pizza, who can deliver to the caravan, or collection.
-Fish and chip shop.
- Crazy Golf
- Shop for your convenience, which sales 99% of the things you need.
- Children’s activities, the rangers station, or craft activities in the main complex.
- Daily entertainment
-Bingo
-Children’s entertainment
- A lovely scenic walks, along the fleet. (Not safe for swimming, has a very strong current)
- Amusements, with a lot of 2p games
- Mash and barrel pub, serving pub grub inside and outside seating, with a dog friendly area inside.
-I CAN NOT provide passes for these.!! You can use the amusement’s, the pub without using a pass.


No Smoking, no electric charge of vehicles permitted at the van, facilities for this is in the main car park.

No large groups of same sex people, over 8 people including children and babies in
Please PM if interested, as prices vary.

Guest access
You can let your self in and out using the key safe.
We suggest you always leave the key in the safe, lost keys are very difficult to get sorted at short notice.

Other things to note
Please remember you will need a Haven pass if you want to use the pool or activities.
You do not need a pass for the pub, amusement arcade. A lot of people book and don’t want to use the entertainment passes.

Play Passes Everything You Need To Know

The questions you have about Play Passes will likely depend on whether you’re booking or have already arrived on your Haven holiday. Let’s take you through them.

If you’re looking to book a Haven holiday:

Does my booking include a Play Pass?
If you are booking directly through Haven and select the full Haven holiday package, Play Passes will be automatically included for your party.

If you are booking a Haven Hideaway package or a private letting, you will not automatically receive Play Passes.

All subject to availability.

How long will a Play Pass be valid for?
Play Passes are valid for the duration of your holiday and are secured in advance by booking a Haven holiday. We don’t currently offer Play Passes (to purchase while) on park.

I'm a Private Letting guest. Can I purchase Play Passes?
Private Lettings guests have the option to purchase Play Passes through Haven directly. If you're a private lettings guest, please click here for information and pricing, as this will be different for your break.

I'm a Hideaway guest. Can I purchase Play Passes?
Play Passes are not included as part of a private bookings.

Can I purchase a day pass?
Play Passes are applied for the duration of your booking only. Day guests are not permitted.

If you’ve already arrived on your Haven holiday:

Where can I find my Play Passes when I arrive?
You’ll be given your Play Passes at the gate on arrival.
How do I use my Play Pass on my Haven holiday?
It’s good practice to always carry your Play Passes around with you as you’ll need to produce these to go swimming, book activities and get into our entertainment venues.

Weymouth beach is a short drive away, it’s a very safe beach for children, also part of the beach is dog friendly all year.

You will need to provide your own bedding (quilts and pillows supplies), towels, tea towels, loo roll etc.

BBQ grill • Pets allowed • TV • Pool • Smoke alarm • Fire extinguisher • Outdoor dining area • Free parking on premises • Smoking allowed • Carbon monoxide alarm

Everdene, a beautiful warm & contemporary 3 bedroom holiday cottage located in Upwey village near to Weymouth Beach, ideally located for families & friends to holiday & explore Dorset.

Spacious Everdene has a master king size bedroom upstairs with a large luxury ensuite bathroom, 2 further bedrooms downstairs with flexible twin or double set up for your group & a second family bathroom. Everdene has beautiful views over the meadows with a private garden too. More dates available on request

The space
Everdene is a really special holiday cottage, this barn style modern luxury villa is purpose built and centrally located in a beautiful holiday setting. We hope to have thought of all the things that will make your stay great, if there is anything specific you need please just ask!

The 3 bedrooms are all a good size with fitted wardrobes including plenty of hanging and drawer space for your belongings. The beds are comfortable 1000 spring beds with bounce back pillows, quality linen and towels. There is a smart TV and hairdryer in each bedroom and black out roller blinds for a brilliant nights sleep. The showers have hot water on demand and have good water pressure for your enjoyment. The baths are a good size and are white and clean ready for you to relax in.

The living area is open plan, light, airy and spacious. The kitchen is well equipped with up to date appliances including an electric hob, oven, microwave, dishwasher, washer/dryer, fridge and freezer. There is also a toaster, kettle, cafetiere with plenty of cutlery and crockery for adults and children alike.

The open plan kitchen has a good sized dining table and comfortable lounge area with a smart TV and DVD player.

The view from the living area and the decked patio is particularly relaxing with a south west facing decked area in the sun, this overlooks the courtyard and the stunning meadow leading on to fields where you are likely to spot deer, rabbits and kestrels amongst other wildlife. The cottage also has an enclosed private garden to the side of the property with outside seating, benches, laundry line (retractable so you don't have to look at it) and most importantly a coal BBQ for those warmer evenings together.

In terms of accessibility, Everdene offers accommodation without the need to use any stairs, the downstairs level includes bedroom, bathroom and living areas. Only the 3rd bedroom and ensuite is upstairs.

There are beautiful local walks into the village of Upwey and many footpaths to explore.

Please ask if you are interested in other dates, they are not always made available on Airbnb,

Hope to see you soon at North Manor Meadow, we would love to host your stay

Guest access
The whole house is yours, with a private gated garden, private decked area for dining which looks out onto the courtyard and shared meadow.

There is 2 non- allocated parking spaces with this property in the large accommodating driveway.

Other things to note
Everdene is set in a group of 5 holiday cottages and can be booked as a group or individually, contact me for details.

Pet Owners:

We’re delighted to welcome you and your pets to Everdene Cottage! One pet is included in the price of your stay, and if you'd like to bring additional pets, we’re happy to consider this at the owner's discretion for a small fee. Please feel free to reach out to discuss your needs.

To ensure all our guests enjoy a comfortable stay, we kindly ask pet owners to follow these guidelines:

Unattended Pets: Pets should not be left alone in the cottage to avoid distress or disruption.

Furniture: We ask that pets remain off the furniture to keep everything clean and fresh for all guests.

Clean-Up: Please clean up after your pets promptly.

Meadow Etiquette: In communal areas, such as the meadow, pets should remain on a lead to respect other guests and their space.

Your cooperation helps us maintain the high standards of our cottages and create a welcoming environment for everyone.

Thank you for your understanding and consideration!

Our luxurious accommodation, ‘The Fleet Retreat’ boasts views of the Fleet Lagoon, a stunning nature reserve nestled between world famous Chesil beach and the South West Coast Path. It is situated just 1 mile from Portland and 2 miles from Weymouth town centre

Our luxurious accommodation is in close proximity to an abundance of beaches, walks and activities. It is perfect for couples wanting to while away a lazy weekend or for families wanting to explore all that Dorset has to offer.

The space
The Caravan

The Fleet Retreat is a modern, beautifully furnished and well equipped static caravan located on a 5* family owned holiday park. With a south facing veranda and plenty of outside space, our accommodation has beautiful views over the Fleet Lagoon and Ferry Bridge.

Modern furnishings are a staple of the property, which is finished to a high spec throughout. The stylish kitchen contains everything you could possibly want and more for your stay, with pots, pans, crockery and glassware galore.

There is one king bedroom with a large fitted wardrobe, dressing table and ample space for you and your belongings to spread out after a busy day.

The second bedroom is a twin - perfect for children and there is a double sofa bed in the living area.

Additionally, there are two bathrooms, both with showers.

All bed linen and towels are provided as well as toiletries and kitchen essentials, so there is no need to pack the kitchen sink, all you need to bring is yourself!

The Holiday Park

The Fleet Retreat is situated on the five star family run holiday park 'Chesil Beach', part of the Waterside Holiday Group. Chesil Beach Holiday Park boasts plenty of facilities, which you are more than welcome to take advantage of during your stay.

As a guest at The Fleet Retreat you will have access to:

- Indoor leisure complex with gym, pool, sauna and solarium. *Please note* there is a small charge for use of this facility - £7 adult day pass, £5.50 child day pass, £35 adult week pass and £27.50 child week pass (Prices are correct as of 2025)

- On site entertainment

- Bar & Breeze Restaurant

- Laundry

- Soft play area

- Outdoor play area suited to younger kids

- Outdoor gym

- Chesil Venue

- Outdoor terrace area

- Sports field

Guest access
The Fleet Retreat is completely self contained. Guests have a private gated entrance, parking for two cars and complete use of the two bedrooms, two bathrooms, lounge, kitchen and veranda.

Other things to note
-WiFi -
Access is controlled by Chesil Vista rather than ourselves and as such any problems with accessibility should be directed at reception rather than ourselves. Efforts will be made to ensure connectivity throughout your stay, however in the unfortunate event of breakdown refunds will not be offered.

- Laundry - washing machines and tumble dryers are located in an on site laundry rather than in the caravan itself.

- Pets - we are pet friendly and welcome two well behaved dogs (sorry no very young puppies) into our home. We respectfully ask that pets are not allowed on the furniture and are not left unattended in the property for any period of time.

We endeavour to give your holiday experience a personal touch, providing complementary baked goods, snacks, refreshments and cosmetics during your stay so that the Fleet Retreat feels like a home from home.

We are always here to help, therefore should you require any further information or have any questions please do not hesitate to contact us.

Shampoo • Body soap • Bay view • Sea view • Marina view • Beach view • Hair dryer • Harbor view • Conditioner • Cleaning products

The space
Enjoy our family-owned caravan located in stunning Weymouth. The caravan provides great family holiday,and the caravan park has great facilities for your family including swimming pools, a spa and gym and a venue for first class entertainment.If you love the great outdoors,watersports or just a great seaside holiday this is your perfect destination.

There is an indoor swimming pool onsite for your enjoyment, which has a slide and various depths to cater to all your family

As a self-catering caravan, you'll find everything you need for a perfect stay.
The kitchen has a fridge, a hob, an oven, a toaster, a kettle, a freezer, and a microwave. Veranda and BBQ, along with the outside table and chairs.

The carqvan is a perfect place to relax and offers television and internet access.

The caravan is accessible by a gated ramp, allowing easy access to the door.

This caravan has 2 bedrooms and can comfortably sleep 6.
In the first bedroom, you will find a kingsize bed.
The second bedroom contains a double bed or twin
There is additional sleeping space in the lounge comprising of a pull-out double sofa bed.

There is bathroom,has a toilet and sink and a walk-in shower, a toilet seat, and a raised toilet seat and seat for those who may require them.


House Rules:
Check-in time is 4 pm, and check-out is 11 am.
- Smoking is not allowed.
- There are free parking on premises parking facilities available at the property.
- One well-behaved dog is allowed at the property.

TV • Iron • Carbon monoxide alarm • Stove • Smoke alarm • Wifi • Oven • Garden view • Microwave • Refrigerator

The Summer Lodge boasts uninterrupted views of the Fleet Lagoon and world famous Chesil Beach from its elevated position on the South West Coast Path (Jurassic Coast).

Located just one mile from the Isle of Portland, the home of the 2012 Olympic sailing events and a short drive from Weymouth town centre and harbour, our stunning holiday home is perfectly situated for anyone wanting a coastal escape.

Our sea view lodge sleeps 6 people. There are 2 double bedrooms and a small double sofa bed.

The space
The Lodge

The Summer Lodge has a glass frontage, which allows guests to enjoy the Fleet Lagoon's changing tides and wildlife from the comfort of the large and tastefully furnished open plan living and dining area. Sunsets here really are an incredible spectacle not to be missed and a large veranda complete with outdoor sofas and dining table allows you to relax and take in the view.

Modern furnishings are a staple of the property, which is finished to a high spec throughout. The stylish kitchen contains everything you could possibly want and more for your stay, with pots, pans, crockery and glassware galore.

There are two double bedrooms each with large fitted wardrobe, dressing table and ample space for you and your belongings to spread out after a busy day. Additionally, there are two bathrooms, one with a bath and the other a double shower.

There is a small double sofa bed in the lounge area, which can also be used.

*PLEASE NOTE* - there are no blinds on the large feature window. Please take this into consideration if you plan on using this space for guests to sleep as it does get light in the room on summer mornings.

All bed linen and towels are provided as well as toiletries and kitchen essentials, so there is no need to pack the kitchen sink, all you need to bring is yourself!


The Holiday Park

Summer Lodge is situated on the five star family run holiday park 'Chesil Beach', part of the Waterside Holiday Group. It is located in the private owner’s area, which is separate from the rest of the park and extremely quiet.

Chesil Beach Holiday Park has plenty of facilities, which you are more than welcome to take advantage of during your stay.

As a guest at summer lodge you will have access to:

- Indoor leisure complex with gym, pool, sauna and solarium.

*PLEASE NOTE* there is a small charge for use of this facility - £7 adult day pass, £5.50 child day pass, £35 adult week pass and £27.50 child week pass (Prices are correct for 2025 season)

- On site entertainment

- Bar & Breeze Restaurant

- Laundry

- Soft play area

- Amusement arcade

- Outdoor play area (aimed at younger children)

- Outdoor gym

- Chesil Venue

- Outdoor terrace area

- Sports field with football goals and basketball hoop

Guest access
Summer Lodge is completely self contained. Guests have a private entrance, parking for two cars and complete use of the two bedrooms, two bathrooms, lounge, kitchen and veranda.

Other things to note
-WiFi

*Disclaimer* Wifi access is controlled by Chesil Vista rather than ourselves and as such any problems with accessibility should be directed at reception. Efforts will be made to ensure connectivity throughout your stay, however in the unfortunate event of breakdown refunds will not be offered.

- Laundry - washing machines and tumble dryers are located in an on site laundry rather than in the lodge itself.

- Pets - we are pet friendly and welcome two well behaved dogs (sorry no very young puppies) into our home. We respectfully ask that pets are not allowed on the furniture and are not left unattended in the property for any period of time.

We endeavour to give your holiday experience a personal touch, providing complementary baked goods, refreshments and cosmetics during your stay so that the lodge feels like a home from home.

We are always here to help, therefore should you require any further information or have any questions please do not hesitate to contact us.

Our Sky Deck holiday home is situated on the award winning 5* Chesil Beach Holiday Park. Chesil Beach Holiday Park is part of the Waterside Holiday Group and is situated at the lower end of Wyke Regis, conveniently located near Weymouth and Portland. The Park is adjacent to the South Coast Coastal Path.

The Sky Deck has a incredible view of the Isle of Portland, Portland Harbour, Chesil Beach and Fleet Lagoon over to the open sea.

The space
The Sky Deck is one of the Park’s Signature Grade accommodation and is furnished to a high standard with parking for 2 cars alongside.

As a guest at the 5* holiday park you will have access to the facilities and entertainment on site. There is a nominal fee for use of these facilities and passes can be purchased from Guest Reception. Wifi and other essential information is available and details will be given to guests prior to arrival.

The Sky Deck is very spacious with a large lounge/diner with 2 comfortable sofas (one with pull out double sofa bed) and two armchairs. It has an electric convection fire which will take the chill off the air without heating the whole caravan. There is an extendable table and four chairs for dining at or playing family games.

The fully equipped kitchen has all you need should you not wish to eat at the many local restaurants. It has a full size fridge/freezer, full size electric oven and gas hob, microwave, dishwasher, washing machine, wine cooler, toaster and kettle.

The Master bedroom has a kingsize bed, built in wardrobes and an ensuite with washbasin, WC and shower and patio doors leading onto the veranda The second bedroom has two 2’ 6’’ beds, fitted wardrobe, storage cupboards and TV/DVD. Duvets/pillows and appropriate protectors are supplied.

Bed linen can be provided but if you would prefer to bring your own please indicate on the booking form your preference.

The family bathroom has a bath with shower over, WC and washbasin. Again we can provide towels but would ask that you bring your own towels for the beach or swimming.

On the Sky Deck relax on the outdoor sofa, recliner and chair watching the world go by from your elevated position. On the side veranda there is additional table and chairs perfect for outdoor eating.

The Sky Deck home is let on a NO SMOKING basis and we are unable to accept bookings of Hen or Stag parties (or similar) or groups where all are under the age of 21. BBQs are not permitted anywhere on the decking nor on the area next to the Sky Deck home.

Body soap • Bathtub • Bay view • Hot water • Shampoo • Conditioner • Shower gel • Beach view • Sea view • Harbor view

Welcome to Shepherd Oak - a superb contemporary two bed holiday cottage, perfect for families, business stays, couple retreats or breaks with friends. Shepherd Oak is ideally situated for exploring the Dorset area.

This beautiful countryside setting has amazing views, the lounge looks out onto the wild flower meadow perfect to relax & watch the wildlife. With a well equipped kitchen and smart TVs in every bedroom there is space for all the family to enjoy. More dates available, please check!

The space
Shepherd Oak is a modern yet warm and cosy two bedroom holiday cottage located in the village of Upwey on the outskirts of Weymouth, pet friendly, ideally located for walking and exploring the rolling hills of the Dorset countryside and the Jurassic Coast with its amazing UNESCO world heritage beaches and coastline.

The property has been designed for your holiday comfort with a double bedroom upstairs with built in wardrobes, hair dryer, full length mirror and smart TV, the en-suite shower room is clean and tiled and the upstairs bedroom has a mezzanine over the airy double height lounge with stunning views over the breath-taking Dorset countryside location.

The second bedroom is downstairs and can be dressed as a double or twin room to best suit visitor requirements, the fitted wardrobes and drawers have lots of space, a smart TV and black out blinds are fitted which is great for those with children. The modern bathroom is freshly finished with a shower over the bath combi-boiler with on demand pressured hot water and heated towel rails for your comfort.

The lounge has a smart TV and there is also a DVD player. The open plan living area and kitchen is well equipped to ensure your stay is enjoyable, including a dishwasher, washer/dryer, microwave, toaster, kettle, mini iron board and iron, and caffetiere for your convenience.

The huge windows in the lounge includes a sliding patio door to a decked terrace complete with coal BBQ and outdoor furniture to enjoy the tranquility of the countryside. On a practical level there is a retractable washing line hidden around the side, great for drying off sandy beach towels after a family day out exploring.

We can also provide cots highchairs and stair gates etc. for our younger guests on request.

Guest access
The 2 bedroom cottage, with decked terrace as well as the shared meadow enjoys easy access to the beautiful Dorset countryside straight from the door and a number of popular family and pet friendly beaches are a short drive away. We operate a key locker access so can offer flexible arrival times.
Check in time is from 4pm, however early check in may be available on request for a small additional fee.

Other things to note
Shepherd Oak is set in a group of 5 holiday cottages and can be booked as a group or individually, contact me for details.

Pet Owners:

We’re delighted to welcome you and your pets to Shepherds Oak Cottage! One pet is included in the price of your stay, and if you'd like to bring additional pets, we’re happy to consider this at the owner's discretion for a small fee. Please feel free to reach out to discuss your needs.

To ensure all our guests enjoy a comfortable stay, we kindly ask pet owners to follow these guidelines:

Unattended Pets: Pets should not be left alone in the cottage to avoid distress or disruption.

Furniture: We ask that pets remain off the furniture to keep everything clean and fresh for all guests.

Clean-Up: Please clean up after your pets promptly.

Meadow Etiquette: In communal areas, such as the meadow, pets should remain on a lead to respect other guests and their space.

Your cooperation helps us maintain the high standards of our cottages and create a welcoming environment for everyone.

Thank you for your understanding and consideration!