Best Short-Term Rentals in Fairfield

The Circle Hotel Fairfield offers visitors the charm and historic character of a New England hotel. The hotel features ADA compliant rooms and facilities. Circle Hotel Fairfield offers amenities including in-room WiFi, Roku Streaming Services, mini-refrigerators, and an outdoor terrace. Business travelers appreciate the convenience of free high-speed Internet access, two private meeting rooms (subject to availability) and access to copy and fax services. The Circle Hotel Fairfield is located on the Post Road at the Circle, in the heart of Fairfield – minutes from Interstate 95 and Metro North train station, and convenient to local beaches, golf courses, shops, and parks. In addition to housing the Circle Diner on-site, there are a variety of fine restaurants in the area.

- "I used this property as my base for traveling to beaches, New Haven and back to Stamford. It was excellent. Very close w" - "Fairly priced, clean, perfect" - "Stayed to go to a concert in Bridgeport. Was pleasantly surprised by the accmodations" - "I was late to breakfast at nine am, but there were still two eggs for me to eat. I e chocked for breakfast. Staff total" - "Cute hotel with lots of charm. Loved the decor." - "It was a great stay for our family. If we need to be in that area again, we would definitely stay ag"

Beach fun in seasonal outdoor pool, near Fairfield Museum and History Center
This smoke-free hotel features a restaurant, a seasonal outdoor pool, and a 24-hour front desk. Free continental breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, express check-out, a picnic area, and a lobby fireplace are onsite.
Weekly housekeeping is available.
The Circle Hotel Fairfield offers 80 accommodations with hair dryers and irons/ironing boards. Beds feature premium bedding. 40-inch flat-screen televisions come with digital channels and Netflix. This Fairfield hotel provides complimentary wireless Internet access, with a speed of 25+ Mbps. Cribs/infant beds (surcharge) and rollaway/extra beds (surcharge) are also available. Housekeeping is provided weekly.
Recreational amenities at the hotel include a seasonal outdoor pool.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "Nice place" - "Good family Place" - "Nice comfortable stay" - "Very friendly and helpful staff. Room is very clean and comfortable. " - "Reasonable on Expedia." - "Near Fairfield U" - "Very nice hotel" - "Lovely and cozy! " - "This is an annual destination. Great value and super staff that are friendly and efficient." - "The crew is awesome!" - "Mattresses and pillows are very comfy!" - "Greetings! My spouse and I had the good fortune of staying at the Circle Hotel — twice in the recent past. We had so much fun! Our rooms were medium-sized with two Queen beds, in each nautical-themed room. Maybe it’s partly because my Dad was a Greek sea captain, but we quickly felt “at home.” With that, we found this hotel to have a warm and welcoming energy, largely in part to John’s caring demeanor. He checked us in both times (when we arrived). It was lovely to be greeted and cared for, by such a kind person. And Vlad gave us a parting gift in the form of a big smile the next day! We appreciate the staff there who helped to make our stay special. Also, the continental breakfast is simple yet delightful. While, tbh, I’d enjoy a non-egg protein option (maybe a bowl of almonds and walnuts or something like that?), it sure beats the basic coffee and carbs offered by some establishments. Lastly, we found our rooms (both were on the second floor facing toward the “pool side” of the hotel), to be quiet — which was a needed respite from city living. We also appreciated the view into an open marsh on the backside of the hotel, which provided our eyes and minds with a replenishing mental health break. Overall, we had a terrific time there (the photos speak for themselves), and we hope to return in the near future. : ) Thanks, all! Best, K & G "

Set in Fairfield, 2.2 mi from The Discovery Museum, Hi Ho features a restaurant and free WiFi throughout the property. There is a shared lounge at the property. This property is self-service and express check-in via mobile phone is available. Guests can enjoy various dishes at the on-site restaurant Barcelona. Housatonic Museum of Art is 4.3 mi from Hi Ho, while Beardsley Zoo is 4.3 mi away. The nearest airport is Westchester County Airport, 25 mi from the property.

- "Would not recommend. Also noise from traffic bad" - "We will be back and have already recommended family to stay there while visiting family there." - "Good but appreciate help" - "Beautiful hidden gem for a nice price." - "A good concept but a little to Hi-Tech for their own booking system." - "Good hotel!" - "Served my purpose for one night"

Colonial motel with a restaurant and a bar
Along with a restaurant, this motel has a bar/lounge and express check-in. Free WiFi in public areas and free self parking are also provided. Additionally, express check-out and multilingual staff assistance are onsite.
Weekly housekeeping is available.
Hotel Hi-Ho - Contactless Check-In offers 40 accommodations, which are accessible via exterior corridors and feature espresso makers and complimentary bottled water. Flat-screen televisions are featured in guestrooms.

Guests can surf the web using the complimentary wireless Internet access. Additionally, rooms include hair dryers and irons/ironing boards. Housekeeping is provided weekly.

- "Great" - "Really cool Hotel. We did need weatherstripping on the door. We could hear every car go by. Very Clean and funky decor. Loved it. We had a wonderful dinner at the restaurant. Great location. Very easy check in and check out. I would stay there again, just maybe in a back room. " - "Good location; good restaurant attached to motel." - "Nice property" - "Easily accessible " - "I like the fact that they have Roku instead of the boring basic cable TV most hotels offer. I also like the fact the no contact check-in. As an added bonus, Barcelona Spanish Restaurant is one of the best."

Spacious&Gracious- 5BR Fam-Friendly near I95&Shops is located in Fairfield, just 14 miles from Connecticut Post Mall Shopping Center and 19 miles from The Yale Bowl. Guests staying at this vacation home have access to a patio. Free Wifi is available throughout the property and Silver Sands State Park is 11 miles away. The air-conditioned vacation home is composed of 5 separate bedrooms, 2 living rooms, a fully equipped kitchen with a dishwasher and oven, and 2 bathrooms. Towels and bed linen are available in the vacation home. The accommodation has a fireplace. Guests can relax in the garden at the property. City Hall is 21 miles from the vacation home, while Yale University is 22 miles from the property. Tweed-New Haven Airport is 25 miles away.

Security/Safety • Air Conditioner • Child Friendly • View • Fireplace/Heating • Parking • Internet

While you're here, you can enjoy all the comforts of home and more, including free WiFi and a Smart TV, as well as Netflix and a coffee/tea maker. Other amenities include designer toiletries, pay movies, towels, and a mini-fridge.

- "Great stay" - "Very nice location ! " - "Modern cottage near the beach. Clean and comfortable. Very responsive." - "perfectly clean, quiet, great location " - "Great property and very attentive service, within walking distance of the beach, the town center and train to NY." - "It was perfect exactly as pictured! Clean modern unit with everything you can need. The shower is amazing! Loved every bit of the place. Would totally be worth it to come back for a longer stay in one of the bigger units. The premium studio was perfect what I needed this time around. "

Coastal Retreat Charming 3-Bedroom Fairfield Townhouse near Beaches I Town Center is located in Fairfield, just a 12-minute walk from South Pine Creek Beach and 1.3 miles from Sasco Beach. This property offers access to a balcony and free private parking. Outdoor dining is also possible at the apartment. With free Wifi, this 3-bedroom apartment offers a flat-screen TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are featured in the apartment. The accommodation is non-smoking. You can play table tennis at Coastal Retreat Charming 3-Bedroom Fairfield Townhouse near Beaches I Town Center. Silver Sands State Park is 14 miles from the accommodation, while Connecticut Post Mall Shopping Center is 17 miles away. The nearest airport is Westchester County Airport, 28 miles from Coastal Retreat Charming 3-Bedroom Fairfield Townhouse near Beaches I Town Center.

Pet Friendly • Internet • Child Friendly • View • Ocean View • Other • Parking • Air Conditioner

Hotel in Fairfield with free breakfast and a 24-hour fitness center
This smoke-free hotel features a 24-hour fitness center, a business center, and conference space. Free full breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, dry cleaning, a 24-hour front desk, and free newspapers are onsite.
Best Western Plus Fairfield Hotel offers 60 air-conditioned accommodations with complimentary newspapers and coffee/tea makers. Each accommodation is individually furnished. Flat-screen televisions come with premium satellite channels and pay movies. Bathrooms include shower/tub combinations, complimentary toiletries, and hair dryers.

In-room wireless Internet access (speed: 25+ Mbps) is available for a surcharge. Business-friendly amenities include desks and desk chairs, as well as phones; free local calls are provided (restrictions may apply). Housekeeping is provided daily.

- "Very good" - "Everything was as expected " - "Great" - "Excellent Staff and service. Pls is immaculate" - "Comfortable with homie feel " - "great time." - "Easy checkin, room was clean, bed was soft, complimented breakfast was just enough. " - "The hotel had excellent service staff was excellent very clean room was very clean also and plenty of parking in space for my vehicle and I also liked the complementary breakfast."

Charming Fairfield Cottage By The Sea is located in Fairfield, just a few steps from Fairfield Beach and 14 miles from Silver Sands State Park. Guests can benefit from a balcony and a picnic area. There's a sun terrace and guests can use free Wifi and free private parking. The air-conditioned country house consists of 3 bedrooms, a living room, a fully equipped kitchen with a dishwasher, and 2 bathrooms with a bath and a hair dryer. A TV is offered. The accommodation is non-smoking. Guests at the country house will be able to enjoy activities in and around Fairfield, like cycling, fishing, and canoeing. There is a garden with a barbecue at this property, and guests can go hiking nearby. Connecticut Post Mall Shopping Center is 17 miles from Charming Fairfield Cottage By The Sea, while The Yale Bowl is 25 miles from the property. Tweed-New Haven Airport is 29 miles away.

Sports/Activities • Other • Parking • Guest Services • Ocean View • Pet Friendly • Internet • View • Balcony/Terrace • Air Conditioner • Barbecue/Outdoor Cooking • Security/Safety

While you're here, you can enjoy all the comforts of home and more, including a refrigerator and a flat-screen TV, as well as a coffee/tea maker and a patio. Other amenities include towels, a crib, an ironing board, and housekeeping.

- "Great location, very clean" - "Excellent value" - "The room was cozy, and clean. Management was extremely gracious and helpful, with great information about the area. We would definitely stay there again." - "Everything was beautiful and easy access to the beach " - "Great place. Quiet, clean, right near beach. A great staycation! " - "Enjoyed our stay at this location. Was excited about having beach access included which is harder to come by in this area & day passes for other local beaches as a non resident are about $50 a day ( last time I was in the area ) the Inn included access to fluffy beach towels, chairs & umbrellas . The only thing i found disappointing which isn’t a reflection of the Inn but was the beach itself . For it being a private beach , I expected it to be a lot cleaner an not to see garbage (mostly wrappers) here an there in the water and that the sand would be a little more enjoyable an sandy , not comply covered in shells. We made the best of it but would definitely recommend bringing water shoes . "

Best Western Plus Fairfield Hotel is within 9 minutes of Black Rock Harbor and the Fairfield Metro North Station. It features an on-site gym and comfortable guest rooms with free WiFi. Each spacious room at Best Western Plus Fairfield Hotel provides a refrigerator and coffee maker. There is also a cable TV and ironing facilities. During their stay, guests can enjoy a free hot continental breakfast. The hotel also offers a business center with copy and fax services. Best Western Plus Fairfield Hotel is within 4 miles of Barnum Museum and Beardsley Zoo. It is 7 miles from Sherwood Island State Park and Long Island South.

- "Over all it’s a very good hotell" - "Cozy and comfortable at a good price." - "Convenient for visiting nearby relatives" - "good comfort for a few nights" - "Fairfield: A Bit More Than Fair" - "Overall, it was good." - "Badic Hotel, does the job" - "The beds were very comfortable and the people there were friendly." - "Dissapointed"

Summary:
479 Benson Road is a beautiful 2 bedroom, 1.5 bathroom private home in a duplex community in the highly desirable Fairfield community. This single-family residence is. just steps away from downtown Fairfield, Fairfield Marina, and Jennings Beach.

The Space:
This gleaming two-story home is located and designed for easy Connecticut living. Work from home with high-speed internet, enjoy a day at the beach and walk to your choice of fine dining, shopping, and entertainment at night, cook up a BBQ on the spacious backyard patio or take a dip in the pool.

The Neighborhood:
Fairfield is a charming New England community featuring 5 miles of shoreline on the Long Island Sound. With close proximity to NYC, major highways like 95, and the Merritt Parkway, you’ll be in a commuter-friendly location.

479 Benson Road is nestled in a charming neighborhood with a community packed with picturesque streets and friendly neighbors, creating a warm and welcoming atmosphere. Within close proximity, you’ll find a variety of local places to go and things to do.

Take a stroll or bike ride to the beautiful Jennings Beach where you can soak up the sun, swim in the sparkling waters, or enjoy a picnic with family and friends. For nature enthusiasts, Fairfield is home to Lake Mohegan and Fairfield Woods Nature Preserve, offering scenic trails for hiking

If you’re looking for shopping and dining options, Fairfield’s Brickwalk is just a short distance away. Explore the boutiques, shops, and restaurants that line the streets.

Getting Around:
With nearby bus stops and train stations, residents can easily commute to neighboring towns or venture into New York City.

The Metro-North Railroad Fairfield station is just a short distance away, offering efficient train services along the New Haven Line. Whether you're heading to work, exploring the city, or simply enjoying a day out, living at 479 South Benson ensures effortless transportation connectivity for all your needs.

Other Things to Note:
At Compass Furnished Apartments, the security and integrity of our bookings are our top priorities. We utilize Authenticate for identity verification to ensure a safe and trustworthy experience for all our guests. Please Note: If a booking does not pass the identity verification process, we reserve the right to cancel the reservation. We appreciate your understanding as we strive to maintain a secure environment for everyone.

Interaction with Guests:
Check-in instructions will be provided via email 7 days and 24 hours before check-in.

- "Very clean and comfy rental......great neighborhood for walking....beach very close....."

Cozy condo with yard and patio. Long-stay discount available offers accommodations in Fairfield, 10 miles from Silver Sands State Park and 13 miles from Connecticut Post Mall Shopping Center. This property offers access to a balcony, free private parking, and free Wifi. Outdoor seating is also available at the apartment. The air-conditioned apartment consists of 3 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a walk-in shower and a hair dryer. Towels and bed linen are featured in the apartment. For added privacy, the accommodation has a private entrance and soundproofing. Guests at Cozy condo with yard and patio. Long-stay discount available can enjoy hiking nearby, or make the most of the garden. The Yale Bowl is 19 miles from the accommodation, while City Hall is 21 miles away. Tweed-New Haven Airport is 25 miles from the property.

- "Great property"

3 Bed/2 Bath. 1st level Primary Suite with walk in closet & jetted bathtub.

Cathedral Ceilings. Living room with comfy, pullout sofa & working fireplace, plus Sunroom with French doors out to the deck & pool.

Large, fully equipped Gourmet Kitchen with dining area. High end Stainless Steel Appliances & built-in lobster steamer!

Fully fenced and gated yard. Separate, large patio with Gas Grill and dining area.

Courtyard with fire pit, hammock and herb and blackberry garden for picking!

Air Conditioner • Guest Services • View • Kitchen • Security/Safety • Ocean View • Internet • Pool • Barbecue/Outdoor Cooking • Other • Oceanfront • Hot Tub

Sunny & Spacious 2BD 1BA WFH Apt-Huge Yard & Patio is located in Fairfield, just 22 miles from City Hall and 23 miles from Russian Railway Museum. The property is around 14 miles from Connecticut Post Mall Shopping Center, 19 miles from The Yale Bowl, and 21 miles from Yale University. Free Wifi is available throughout the property and Silver Sands State Park is 10 miles away. The apartment consists of 2 separate bedrooms, 1 bathroom, and a living room. The accommodation is non-smoking. Guests can relax in the garden at the property. Richter Park Golf Course is 28 miles from the apartment, while Thimble Islands is 30 miles from the property. Tweed-New Haven Airport is 25 miles away.

Internet • Air Conditioner • View • Child Friendly • Parking • Fireplace/Heating • Security/Safety

While you're here, you can enjoy all the comforts of home and more, including free WiFi and a billiards table, as well as a bidet and air conditioning. Other amenities include a video library, a stereo, a foosball table, and housekeeping.

Child Friendly • Fireplace/Heating • Internet • Sports/Activities • Other • Air Conditioner • Entertainment

Located in Fairfield, a few steps from Penfield Beach, DUNE Fairfield Beach provides accommodations with free bikes, free private parking and a private beach area. The property is around 14 miles from Silver Sands State Park, 17 miles from Connecticut Post Mall Shopping Center and 24 miles from The Yale Bowl. Russian Railway Museum is 26 miles away and State University of New York at Purchase is 30 miles from the inn. Guest rooms has air conditioning, a fridge, a microwave, a coffee machine, a shower, free toiletries and a closet. With a private bathroom equipped with a hairdryer, rooms at the inn also offer free WiFi, while certain rooms include a balcony. At DUNE Fairfield Beach, each room is equipped with a seating area. City Hall is 24 miles from the accommodation, while Yale University is 25 miles away. Tweed-New Haven Airport is 29 miles from the property.

- "Dune Fairfield Beach is a wonderful and comfortable place to stay." - "We loved it overall and plan to return." - "Expensive but very nice/met all expectations" - "Disappointing. The noise from the bar next door was unacceptable."

Charming Beach Cottage – Steps from Private Beach!
Welcome to our newly renovated seaside retreat—a perfect getaway for families, couples, or anyone looking to relax by the shore. Nestled just steps from a private beach (right across the street!), our charming cottage offers the ideal balance of coastal tranquility and convenient access to town. Whether you enjoy walking, biking, swimming, fishing, kayaking, or simply napping in a shady hammock, this is the place for you.

The Cottage
Our cozy-yet-modern cottage has been thoughtfully updated while maintaining its rustic seaside charm. With plenty of indoor and outdoor space, it’s perfect for a family getaway or a peaceful escape. Enjoy high-speed WiFi, or take advantage of the many opportunities to unplug and unwind.

For entertainment, we’ve added Amazon Alexa and a Fire Stick to our smart TV, so you can stream your favorite shows and music effortlessly.

Work & Play
Need to mix business with pleasure? We’ve partnered with B@Work Co-Working, offering our guests 24/7 access to a beautiful, multi-level workspace overlooking a lake and waterfall, just 3 miles from the cottage.

Guest Access
Guests will have exclusive use of the entire cottage, plus unlimited access to the sunshine, sand, and sea.

Local Highlights
While it’s easy to hide away and relax for a week or more, Fairfield is also full of fantastic dining, craft breweries, and live entertainment:

Foodie Paradise: From fresh seafood and sushi to pizzas, burgers, and barbecue, there’s something for everyone just blocks away.
Local Brews: Discover Fairfield’s thriving microbrewery scene with fantastic craft beer options nearby.
Live Music & Entertainment: Catch a show at Fairfield Theater Company or The Quick Center (Fairfield University), or experience one of the state’s best weekly open mic nights at Acoustic Café in Black Rock.
Getting Around
Bike to town (or take a leisurely walk)
Quick drive or Uber trip to downtown Fairfield
Half a mile from the Fairfield Metro North Train Station (~1 hour to Manhattan)
Easily accessible from I-95 & Merritt Parkway
Parking
On-site parking for up to three vehicles
As a beach cottage, the parking area is small
If parking multiple vehicles, they must be parked perpendicular under the cottage
Beach Access & Guidelines
We have a right-of-way to the private beach across the street. Guests may enjoy the beach up to the high tide mark but please respect our neighbors' property.

Book your perfect beach getaway today and make lasting memories by the beautiful Long Island Sound!
The most important House Rule is, respect our neighbors and community. Mystic is a quaint, coastal New England town. As hosts, and guests, we share in the responsibility of keeping Mystic a great place to visit, and to LIVE. Honor the noise ordinance. Be the guest that you would want staying in a vacation rental near your home.

We provide detailed instructions for using our Right of Way, to access our Deeded Beach Rights across the street.

- "The cottage was perfect. All of the basics were supplied such as toilet paper, paper towels, pack and play, booster seat etc. Check in and check out were easy with very little for us to do. Gerard was extremely helpful. He is one of the most efficient and kind property managers that I have ever dealt with. He answered every question I had and provided information about the area.The beach area was clean and quiet. Beds were comfortable and the backyard space was great with the kids!"

Fairfield Cottage -Top Rated Gem, Fire Pit, Near Beach, 90 Min to NYC is located in Fairfield, just 11 miles from Silver Sands State Park and 14 miles from Connecticut Post Mall Shopping Center. The property is around 20 miles from The Yale Bowl, 22 miles from City Hall, and 22 miles from Yale University. There's a picnic area and guests can use free Wifi and free private parking. Featuring garden and quiet street views, this recently renovated vacation home offers 3 bedrooms and opens to a patio. The air-conditioned vacation home also features a flat-screen TV, a fully equipped kitchen with a dishwasher, a seating area, washing machine, and 2 bathrooms with a bath and a shower. The property has an outdoor dining area. For those times when you'd rather not eat out, you can cook on the barbecue. For guests with children, the vacation home provides outdoor play equipment and a baby safety gate. Guests at Fairfield Cottage -Top Rated Gem, Fire Pit, Near Beach, 90 Min to NYC can enjoy snorkeling and hiking nearby, or make the most of the garden. Russian Railway Museum is 23 miles from the accommodation, while Richter Park Golf Course is 27 miles from the property. Tweed-New Haven Airport is 26 miles away.

- "Would certainly return when in the area!"

Recently renovated 3 bedroom 2 bathroom ranch. The first room has a full size bed that can accommodate 2 guests, and the second room has a king size bed that can accommodate 2 guests as well and the third room has king size bed that can accommodate 2 more guests.

- "We needed a house for our family to attend a funeral. Host was attentive and house was as pictured on line. Thank you, Jon!" - "We had a great time staying at your house with two other couples. The house is beautiful and was just what we needed for a weekend in Fairfield. We would definitely stay here again!" - "The house was beautiful and looks exactly like the pictures. It has everything you need if you want to cook from home after catching some fish, which was what my husband and his buddy did one night. Everything was clean and the beds were comfortable. We had a great stay at Jon’s house!"