Fairfield Vacation Rentals

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Fairfield vacation rentals

A beach with a wooden fence and rocks, leading to the water.

1. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (119 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
$180 nightly
The price is $268
22 Nov - 23 Nov
Total with taxes and fees
DUNE Fairfield Beach
A covered outdoor seating area with wicker sofas, a fire pit, and string lights.

2. Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Tunxis Hill
10.0 out of 10, Exceptional, (2 reviews)
"Host was attentive and the space was comfortable and exactly what we needed"
United States
Parker M.
$150 nightly
The price is $332
15 Nov - 16 Nov
Total with taxes and fees
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
A modern kitchen with stainless steel appliances, a wooden island, and pendant lighting.

3. Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
West End - West Side
9.6 out of 10, Exceptional, (5 reviews)
"Nice place to stay "
United States
Maria Elena G.
$163 nightly
The price is $373
18 Nov - 19 Nov
Total with taxes and fees
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

4. Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (41 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
$201 nightly
The price is $551
18 Nov - 19 Nov
Total with taxes and fees
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
A wooden deck with a white sofa, overlooking a residential area with houses and a view of the sea.

5. Stareway to Heaven in Fairfield

Stareway to Heaven in Fairfield
2.0 star property
Fairfield Beach
$909 nightly
The price is $1,302
24 Nov - 25 Nov
Total with taxes and fees
Stareway to Heaven in Fairfield
A dining area with a wooden table and chairs, a white bench, and a window with a view of a brick building.

6. Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (19 reviews)
"Beautiful home, clean and exactly as described.We loved our stay and plan on returning.The host was wonderful to work with.An overall excellent experience."
United States
Tara C.
$280 nightly
The price is $650
30 Nov - 1 Dec
Total with taxes and fees
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
A wooden deck with a white railing, a white sofa, and a view of houses and the sea.

7. Stareway to Heaven Su

Stareway to Heaven Su
Fairfield Beach
10.0 out of 10, Exceptional, (25 reviews)
"Great property right on the beach!!!! Very clean and the perfect elevated stay for our weekend Would recommend this property again and again!!!"
United States
Amanda B.
$765 nightly
The price is $1,042
24 Nov - 25 Nov
Total with taxes and fees
Stareway to Heaven Su
Ideal for meals and memorable gatherings.

8. Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
Tunxis Hill
9.6 out of 10, Exceptional, (22 reviews)
"The house is very clean and spacious! Great location for what my party needed. The host is incredibly responsive and very helpful. Overall this was a fantastic stay and would recommend. "
United States
Emily K.
$376 nightly
The price is $768
15 Nov - 16 Nov
Total with taxes and fees
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

9. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
3.0 star property
Tunxis Hill
4 Mi to Beach & Dtwn! Charming Fairfield Home
A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

10. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
Tunxis Hill
6.0 out of 10, (2 reviews)
"Beautiful home! Host was super responsive to questions. The entire house was super clean and welcoming. The bed was comfortable and smelled fresh. There was a personalized welcome sign that was a nice touch and some (much needed) snacks after our almost 3 hour drive. Expectations were well within reason and easily manageable. I would 100% rent again."
United States
Raelyn O.
$520 nightly
The price is $884
15 Nov - 16 Nov
Total with taxes and fees
4 Mi to Beach & Dtwn! Charming Fairfield Home
A modern living room with a flat-screen TV, a grey sofa, a coffee table, and a large plant.

11. Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
$134 nightly
The price is $246
19 Nov - 20 Nov
Total with taxes and fees
Spacious Studio with Pool Table
A bedroom with a large arched window, a bed, a bedside table with a lamp, and a small seating area with cushions and a plant.

12. Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Downtown Bridgeport
9.4 out of 10, Exceptional, (19 reviews)
"A hidden gem! We have stayed here twice now when attending concerts at Hartford Healthcare Amphitheater. A beautifully appointed room within walking distance to the shows!"
United States
Kim F.
$140 nightly
The price is $222
16 Nov - 17 Nov
Total with taxes and fees
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
A swimming pool at night with blue lighting.

13. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (60 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
$90 nightly
The price is $144
15 Nov - 16 Nov
Total with taxes and fees
Business or Weekend escape
Modern dining furniture complementing the living space.

14. Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (3 reviews)
"We had an awesome time staying Here Everything was super clean And the communication with the host was great we would greatly recommend would definitely stay again!"
United States
Anonymous traveler
$123 nightly
The price is $300
30 Nov - 1 Dec
Total with taxes and fees
Renovated 2BR Retreat / Modern Comforts Included
A modern kitchen with wooden cabinets, a stainless steel sink, a microwave, a kettle, and a dish rack.

15. Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
8.0 out of 10, Very good, (7 reviews)
"Cute and efficient property, and a great location. The host was very prompt with any and all questions. Definitely recommend the place for a quick get away."
United States
Joshua L.
$160 nightly
The price is $352
19 Nov - 20 Nov
Total with taxes and fees
Modern 2 Bed in BlackRock
A modern living room with a sofa, a coffee table with decorative items, and a large window with curtains.

16. Luxury Designer 2 bedroom+office/3bed vacation home.

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (29 reviews)
"Great location and clean property. Some items were broken or missing, but overall, a nice stay."
United States
Cherie
$143 nightly
The price is $396
15 Nov - 16 Nov
Total with taxes and fees
Luxury Designer 2 bedroom+office/3bed vacation home.
A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

17. Centric property close to all the great things in the city

Centric property close to all the great things in the city
Brooklawn - St. Vincent
6.8 out of 10, (18 reviews)
"This rental was great accommodation"
United States
Alma B.
$158 nightly
The price is $256
18 Nov - 19 Nov
Total with taxes and fees
Centric property close to all the great things in the city
A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

18. Elite room stay

Elite room stay
Bridgeport
$207 nightly
The price is $328
14 Nov - 15 Nov
Total with taxes and fees
Elite room stay
Private kitchen

19. The B&W Haven: Stylish 3BR Escape with Private Office by LI Ferry

The B&W Haven: Stylish 3BR Escape with Private Office by LI Ferry
Brooklawn - St. Vincent
10.0 out of 10, Exceptional, (1 review)
"."
United States
Matthew R.
$138 nightly
The price is $343
16 Nov - 17 Nov
Total with taxes and fees
The B&W Haven: Stylish 3BR Escape with Private Office by LI Ferry
A large, two-story building with a symmetrical facade, multiple windows, and a covered porch area.

20. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"it was amazing will stay again food was good comfort was great "
United States
anthony
$339 nightly
The price is $390
1 Dec - 2 Dec
Total with taxes and fees
Guesthouse at Norwalk Inn
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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Top Fairfield Hotel Reviews

A bar with a stone wall, multiple shelves of bottles, and bar stools.
Delamar Westport

Delamar Westport

Delamar Westport
Westport

10/10 Excellent

Pool and sauna were an excellent part of the experience. Breakfast buffet was top notch. The moment we arrived, the valet crew and front desk staff made me feel completely relaxed. I knew instantly that I made the right choice booking a stay at Delamar.
United States
James
Reviewed November 9, 2026
Delamar Westport

Frequently Asked Questions

Can I find vacation rentals in Fairfield?

Yes, there are vacation rentals in Fairfield close to Fairfield Theater Company, or you can select a more remote option if you'd like a relaxing place to stay. Discover why Fairfield is known for its shops and beaches. While you're here, grab a bite or have a drink at the restaurants.

How many vacation rentals are there in Fairfield?

With 48 Expedia vacation rentals, you're sure to find just the right place for your Fairfield stay.

What can I see and do in Fairfield?

Enjoy the outdoors at Penfield Beach and Fairfield Beach, or simply take in cultural attractions like Fairfield Theater Company and Connecticut Audubon Birdcraft Museum. Jennings Beach and Lake Mohegan are other places to visit while you're in town.

What are vacation rentals like in Fairfield?

Vacation rentals are privately owned accommodations you can book for several days or longer in Fairfield. Vacation rentals offer extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for family trips.

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