Book Holiday Homes in Fairfield

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Featured Holiday Homes in Fairfield

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Greenwich
The price is NZ$362 per night from 9 Nov to 10 Nov
NZ$362
9 Nov - 10 Nov
includes taxes & fees
Stay at this vacation home in Greenwich. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Houston Preserve and E. Gaynor Brennan Golf ...
Opens in a new window2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Cozy Ocean Front Retreat with Private Beach!

Cozy Ocean Front Retreat with Private Beach!

Milford
Book a stay at this beach vacation home in Milford. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions Walnut Beach and The Coastal ...
Opens in a new windowCozy Ocean Front Retreat with Private Beach!
Business or Weekend escape

Business or Weekend escape

Stratford
The price is NZ$246 per night from 4 Nov to 5 Nov
NZ$246
4 Nov - 5 Nov
includes taxes & fees
Stay at this vacation home in Stratford. Enjoy an in-room coffeemaker and air conditioning. Our guests praise the helpful staff in our reviews. Popular attractions ...
Opens in a new windowBusiness or Weekend escape
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McAngel Haven: 5 mins from Yale

McAngel Haven: 5 mins from Yale

West Haven
The price is NZ$921 per night from 4 Nov to 5 Nov
NZ$921
4 Nov - 5 Nov
includes taxes & fees
Book a stay at this family-friendly vacation home in West Haven. Enjoy laundry facilities, patios, and an in-room coffeemaker. Popular attractions Cullman-Heyman ...
Opens in a new windowMcAngel Haven: 5 mins from Yale
Newly renovated Private bedroom near Stony Brook University

Newly renovated Private bedroom near Stony Brook University

2 out of 5
Stony Brook, NY
The price is NZ$406 per night from 4 Nov to 5 Nov
NZ$406
4 Nov - 5 Nov
includes taxes & fees
Stay at this vacation home in Stony Brook. Popular attractions Long Island Museum of American Art, History, and Carriages and Island Federal Credit Union Arena ...
Opens in a new windowNewly renovated Private bedroom near Stony Brook University
Cozy 3 bedroom minutes from Yale and the beach

Cozy 3 bedroom minutes from Yale and the beach

West Haven
Stay at this vacation home in West Haven. Enjoy free WiFi, private pools, and air conditioning. Popular attractions Sandy Point Beach and New Haven Harbor are ...
Opens in a new windowCozy 3 bedroom minutes from Yale and the beach
Stay at Black Rock Harbor

Stay at Black Rock Harbor

Bridgeport
Stay at this vacation home in Bridgeport. Enjoy a garden, an in-room coffeemaker, and air conditioning. Popular attractions Longfellow Park and Seaside Beach ...
Opens in a new windowStay at Black Rock Harbor
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Stamford
Stay at this vacation home in Stamford. Enjoy laundry facilities and air conditioning. Popular attractions Mill River Park and West Beach are located ...
Opens in a new windowGem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Brookfield
Book a stay at this family-friendly vacation home in Brookfield. Enjoy a garden, laundry facilities, and a pool table. Popular attractions Lions Park and DiGrazia ...
Opens in a new windowLakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fairfield Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Fairfield vacation homes are the perfect way for you to wing it.

Holiday houses in Fairfield let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Fairfield in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Fairfield adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Fairfield with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Fairfield vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Fairfield Holiday Homes essential information

Accommodation
439 Holiday Homes
Lowest Price
NZ$246
Highest Price
NZ$921
Popular accommodation
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock., Cozy Ocean Front Retreat with Private Beach!, Business or Weekend escape, McAngel Haven: 5 mins from Yale, Newly renovated Private bedroom near Stony Brook University, Cozy 3 bedroom minutes from Yale and the beach, Stay at Black Rock Harbor, Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi, Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Top trending hotels in Fairfield

The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
417 Post Road, Fairfield, CT
Fully refundable
Stay at this 3-star beach hotel in Fairfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
Opens in a new windowThe Circle Hotel Fairfield
Hotel Hi-Ho - Contactless Check-In

Hotel Hi-Ho - Contactless Check-In

3 out of 5
4180 Black Rock Turnpike, Fairfield, CT
Fully refundableReserve now, pay when you stay
Stay at this 3-star motel in Fairfield. Enjoy free WiFi, free parking, and room service. Our guests praise the restaurant and the clean rooms in our reviews. ...
Opens in a new windowHotel Hi-Ho - Contactless Check-In
Best Western Plus Fairfield Hotel

Best Western Plus Fairfield Hotel

2.5 out of 5
100 Kings Highway Cutoff, Fairfield, CT
Fully refundableReserve now, pay when you stay
The price is NZ$301 per night from 4 Nov to 5 Nov
NZ$301
4 Nov - 5 Nov
includes taxes & fees
Book a stay at this business-friendly hotel in Fairfield. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
Opens in a new windowBest Western Plus Fairfield Hotel
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DUNE Fairfield Beach

DUNE Fairfield Beach

3 out of 5
1160 Reef Rd, Fairfield, CT
Stay at this 3-star beach apartment in Fairfield. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions Penfield Beach and Fairfield ...
Opens in a new windowDUNE Fairfield Beach
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.