Vacation rentals in Fairfield

4.9 out of 5 average rating, 109 reviews

Fairfield 2nd Fl–2 Rms | Exclusive Entry & Parking

ENTIRE 2nd FL for up to 2️⃣ adult guests ONLY 2️⃣ Rooms➕Skylit Full Bath Exclusive Driveway Parking spots➕Private Main Entrance, separate from full-time renters on 1st FL using back entries Heat & Cool: wall-mounted AC➕portable Dyson ➕ Central AC w/2 sensors - host adjustable remotely TV is Screen only, works with Bluetooth & Chromecast, NO Services Kitchenette: heat/store food (NO cooking), allows affordable stay in affluent Fairfield Town Professional Clean Service Host Assistance Virtually

4.92 out of 5 average rating, 149 reviews

The bedroom features a queen-sized bed with a beige quilt. Natural light enters through two windows adorned with lace curtains. A wooden mirror and bedside tables with lamps complement the space, while a comfortable chair adds to the inviting atmosphere.

Guest suite in Fairfield

Suite; 1 Bedroom & Living Area/Xtra Bedrm; Kitchen

Fully accessorized, large (1,255 sq ft) beautiful suburban space consisting of bedroom (queen), an exclusive-use living room/extra bedroom with twin pull-out bed, private full bath; in-unit washer/dryer; exclusive use of kitchen (was the main kitchen of the house); private entrance to space thru side door of the house. Two large-screen TVs. Unit on the ground floor of a 3 story home. Owners on property. Train station about a mile away (NYC: 70 minutes). Easy walk to Fairfield University.

A staircase is displayed, featuring wooden handrails and white balusters. The stairs are covered with a light gray carpet that extends to the landing at the top. The surrounding walls are painted in neutral tones, enhancing the spacious feel of the area.

4.93 out of 5 average rating, 110 reviews

Downtown Fairfield 3 bedroom Colonial

Enjoy a charming, 3 bed/2 full bath Colonial that is only a 4 block walk from the coffee shops, bars, and restaurants on the Post Road and .7 mile from the Fairfield Train Station. The house is over 1500 sq. feet on a quiet street and only a mile to the town beaches. Work has taken me from Fairfield, but it remains home, so the house is fully stocked with everything. If you're into shooting hoops, you'll like the lined and paved court. Small well-trained dogs and longer stays are negotiable.

4.94 out of 5 average rating, 158 reviews

The kitchen features modern cabinetry and countertops, with a gas stove and a refrigerator visible. A cozy eat-in area with a built-in bench and a table is positioned by a window, enhanced by natural light. A decorative rug adds warmth to the wood floor.

Guest suite in Fairfield

Adorable private apt w/ W/D in lovely neighborhood

Enjoy a lovely experience at this centrally-located studio in-law apartment. It boasts a newly renovated kitchen and bath, king bed with brand new mattress, pull out full size sofa, ample closet space and more. The eat-in kitchen has all you need to feel right at home. The apartment is located adjacent to a nice residential house, but is fully private with your own front and back entrances. There are also no stairs, making it easily accessible. It’s located in a wonderful neighbor in Fairfield.

4.97 out of 5 average rating, 576 reviews

Apartment in Woodmont

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

4.9 out of 5 average rating, 230 reviews

A charming row of brick buildings features large, arched windows with green accents. The walkable area is lined with sidewalk planters, and a person is seen strolling leisurely along the paved path. Street signs and storefronts create a vibrant shopping atmosphere.

Apartment in Westport

Spacious Westport Apt surrounded by nature!

Spacious mother-in-law basement apartment with private entrance that opens to the backyard. Large windows in every room give view to the creek in the backyard and birds welcoming our guests. Two bedrooms with a queen size bed. Walk-in shower. Plenty of space for up to four people. Very family friendly - little humans and furry friends welcome! Centrally located 8 min drive to downtown Westport, Fairfield, or Southport. Beach, golf course, playgrounds, hikes, wonderful bakeries and restaurants.

4.99 out of 5 average rating, 110 reviews

Home in Milford

The ARLO - Walk to Brewery & Restaurants

Newly remodeled and designed, The ARLO combines a seamless blend of luxury & comfort for your family. Walking distance to Dockside brewery & stand-out local restaurants, while only 1 mile from the beautiful Walnut Beach. Enjoy a thoughtful & comfortably designed living room, cook in the chef-style kitchen, indoor/outdoor living with a game room and fully-fenced yard. -Less than 2 minutes to The Tyde wedding venue. -15 min to Fairfield U & Sacred Heart -15 min to YALE -0.2 miles off I-95

A wooden bridge spans a gently flowing stream, connecting two forested areas. Surrounding trees create a lush green canopy, with sunlight filtering through the leaves. Rocky stepping stones lead to the bridge, providing a natural transition from the forest floor to the water's edge.

5 out of 5 average rating, 108 reviews

Peaceful Suburban Colonial w/New Kitchen.

Looking for a clean, cozy, secluded suburban escape that's still close to great shopping, Long Island Sound, and the two Fairfield Universities? Look no further than this newly renovated colonial on a quiet tree-lined street with no through traffic. A park and basketball are just at the end of the street. Trader Joes and other great shopping are a 2 minute drive away. Sacred Heart and Fairfield U are 5 minutes away. We're right across the street in case any of us forgot anything :).

4.96 out of 5 average rating, 138 reviews

An outdoor seating area is featured in front of a modern structure, surrounded by lush greenery. Comfortable chairs encircle a stylish fire pit, while warm lights hang above, enhancing the inviting atmosphere. Stone pavers lead towards an expansive open area, promoting a seamless indoor-outdoor connection.

Cottage in Weston

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

4.96 out of 5 average rating, 149 reviews

Top Rated Gem | Fire Pit | Near Beach, FFU & SHU

Welcome to Fairfield Cottage, a cozy retreat that beautifully combines comfort and stylish design for you and your guests. With thoughtful decor and essential amenities, you'll feel right at home. Conveniently located just 90 minutes to NYC, you can easily visit attractions like the Norwalk Aquarium, Beardsley Zoo, and local farms. Unwind at nearby Jennings and Penfield beaches located just 3 miles away, or explore the charming village of Southport.

4.81 out of 5 average rating, 175 reviews

Guest suite in Wilton

Guest suite with private enter

Private room with private enter and bathroom attached dedicated work space and privat parking. On a 1.5 acres property. With fast internet. Located 5 minutes of walking distance from ASML office park, 5 minutes drive from Norwalk corporate park, 9 minutes drive from Wilton Downtown and 15 min drive from Norwalk train station. Close to a lot of restaurants, coffee shops, stores and parks. The owners live in other part of the house. Family owns cats.

4.98 out of 5 average rating, 127 reviews

A well-equipped kitchenette is visible, featuring white cabinetry and modern appliances including a microwave, refrigerator, and Nespresso machine. Shelving displays decorative items and dining essentials. A small cafe table with two chairs provides a dining area. The space is enhanced by natural light from the adjacent room.

Apartment in Fairfield

Sunny Fairfield Studio Apartment

Enjoy this sunny, newly-renovated, modern Fairfield studio apartment, located in the carriage building of a historic early 1900's house. Great for an individual, couple, or family. Well situated, a short drive to Sacred Heart & Fairfield Universities, downtown Fairfield and the beach, Silverman's Farm and other Easton farms for apple picking, petting zoos, and the like, and Fairfield Metro Station for a 1 hour train ride to NYC.

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Popular amenities for Fairfield vacation rentals

Laptop-friendly workspace

Stay near Fairfield's top sights

Compo Beach12 locals recommend

Sherwood Island State Park10 locals recommend

Jennings Beach14 locals recommend

Other great vacation rentals in Fairfield

4.96 out of 5 average rating, 26 reviews

Once a Pond - time and stress slow down.

A spacious covered deck features a panoramic view of the beach and ocean. Sunlit waters stretch into the distance, while beachgoers can be seen enjoying the sand. The structure's ceiling showcases wood paneling and overhead lighting, enhancing the open atmosphere.

5 out of 5 average rating, 45 reviews

5 Minute Walk to Beach & Downtown Fairfield

4.97 out of 5 average rating, 68 reviews

Modern Beach Bungalow

A charming gazebo is surrounded by manicured lawns and colorful flower beds. The structure features a domed roof with a decorative finial and is supported by white railings and columns. Trees provide a natural backdrop, enhancing the serene outdoor setting.

4.96 out of 5 average rating, 24 reviews

Remodeled Cozy Country Cape

The backyard features a wooden pergola adorned with lights, providing a shaded area for seating. A large red umbrella extends over a dining table, and comfortable seating arrangements invite relaxation. Lush green grass stretches across the yard, bordered by white privacy fencing.

4.9 out of 5 average rating, 21 reviews

Seaside Home - Walk to Beach & Marina

4.94 out of 5 average rating, 86 reviews

A modern bathroom area features a sleek black countertop with a mirror above, softly lit by built-in lighting. The doorway opens to a bedroom with vibrant hand-tinted windows, illuminating the space with color. Towels are neatly arranged nearby.

Apartment in Bridgeport

Stylish Sheek Loft Ricport Studio 2, Downtown

4.95 out of 5 average rating, 20 reviews

A scenic view of a calm waterway is framed by a wooden deck. Two white chairs with blue stripes are positioned for relaxation. A small table holds decorative items, while a dock extends into the water, surrounded by greenery and gentle waves.

Guesthouse in Fairfield

The Creekside Cottage