
Holiday houses in Fairfield
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Top-rated holiday rentals in Fairfield
Guests agree: these stays are highly rated for location, cleanliness and more.

Luxurious Barn With New England Charm
Three decades of tasteful renovations — many using re-purposed material — have rendered this converted barn magazine-worthy. Set-back from the road on 1-acre of wooded land with a babbling brook, this conveniently-located modern home maintains its rustic allure. With 30-foot ceilings, exposed wooden beams, dozens of windows, an array of eclectic furniture, and a grand piano, the charm of the barn is immediately obvious. Perfect for romantic getaways, small retreats, family gatherings, and more.

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.

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.

Cape on the Water
Welcome to our Cape on the Water! This unique property is located on beautiful Ash Creek, an inlet off Long Island Sound offering views of tidal wetlands, including tons of fish, bird, kayakers, paddle boarders, small sail boats etc. The house is a newly renovated Cape Cod with open floor concepts, updated Kitchen and bath rooms. Refinished oak hardwood floors through out the entire house. Brand new large deck. The house has a very cozy feel and has been also updated with brand new HVAC system.

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.

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.

Designer Beach Retreat on Exclusive Cedar Beach
Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

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

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

Spring Sale! CozyCottage/Pet-friendly/ WalktoBeach
Inspired by my Dad's wanderlust and love of sea & sand. Relax and unwind in this completely remodeled, stylish Cottage a block and a half from Long Island Sound and .9 mile to Walnut Beach - walk to coffee, pizza, lobster shack! We offer a modern kitchen, breakfast nook, dining area, natural stone wall, parking and W/D. Located in a charming coastal town - enjoy quiet neighborhood walks, coastal trails, boardwalk, breweries and restaurants. 15 min to Yale/New Haven, 65 mi to NYC.

Delightfully Renovated Colonial Barn by the Beach!
This converted 1766 barn is truly one of a kind! The newly renovated barn is set on 3/4 of an acre, surrounded by crushed seashells and a white picket fence. Here you will find a generous living space, carefully curated to incorporate modern amenities a discerning guest demands, all while maintaining the home's historic charm. Our barn is ideal for families looking for a cozy getaway or for a small group looking to explore Fairfield County and all it has to offer.

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.
Popular amenities for Fairfield holiday rentals
Stay near Fairfield's top sights
Other great holiday rentals in Fairfield

Modern Beach Bungalow

Private Garden Cottage w/ Patio

Remodeled Cozy Country Cape

Charming Riverview Home • Firepit • Train & I-95

Cozy Haven in Fairfield w/ Ample Amenities

River Cottage in Weston, CT

Convenient easy Living- Walk to Beach & Town!

Cozy, updated single family in Fairfield County
When is the best time to visit Fairfield?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $245 AUD | $231 AUD | $231 AUD | $247 AUD | $331 AUD | $349 AUD | $365 AUD | $349 AUD | $279 AUD | $285 AUD | $274 AUD | $300 AUD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Frequently Asked Questions
Where should I stay in Fairfield?
Make yourself at home in Fairfield by choosing from our most frequently booked neighborhoods. We have over 280 vacation rentals in Southport, over 410 vacation rentals in Black Rock, and over 140 vacation rentals in Fairfield Beach.
Are there vacation rentals with a dedicated workspace in Fairfield?
Yes! Work meets play with ease at over 180 vacation rentals in Fairfield featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in apartment rentals in Fairfield?
Experience the best of Fairfield with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Fairfield?
Four-legged friends are welcome in Fairfield. Choose from more than 130 vacation rentals for guests traveling with pets.
Are there Fairfield vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Fairfield, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly vacation rentals in Fairfield?
Fairfield has more than 220 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Fairfield have air conditioning?
Absolutely! We offer over 200 house rentals with air conditioning in Fairfield. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Fairfield have wifi?
Absolutely! We offer over 50 apartment rentals with wifi in Fairfield. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Fairfield have a bbq area?
Absolutely! We offer over 60 house rentals with a bbq area in Fairfield. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Fairfield have a gym?
Absolutely! We offer over 30 house rentals with a gym in Fairfield. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Fairfield

Total holiday rentals
Explore 320 holiday rentals in Fairfield

Nightly prices starting at
Fairfield holiday rentals start at $42 AUD per night before taxes and fees

Verified guest reviews
Over 9,290 verified reviews to help you choose

Family-friendly holiday rentals
220 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 130 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
180 properties have a dedicated workspace

Wi-Fi availability
310 of Fairfield holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Fairfield rentals

4.8 Average rating
Fairfield stays are highly rated by guests—averaging 4.8 out of 5!
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- Times Square
- Madison Square Garden
- New York City Center
- New York University
- Central Park Zoo
- Columbia University
- MetLife Stadium
- Yale University
- Yankee Stadium
- Bronx Zoo
- United Nations Headquarters
- Jones Beach
- Rockefeller Center
- Citi Field
- Empire State Building
- Brooklyn Bridge
- Grand Central Terminal
- Bryant Park
- Radio City Music Hall
- Cooper's Beach, Southampton
- USTA Billie Jean King National Tennis Center
- Thunder Ridge Ski Area
- The Metropolitan Museum of Art
- Fairfield Beach




