Fairfield Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

28 Houses

13

New Contemporary Beach House

Connecticut / Fairfield

Fairfield house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$1,309

Price per night from

$1,309

Great rentals within 20 miles that match your search

Distance approx 9.26 km from Fairfield

25

NEW! Beachfront Cottage on the Long Island Sound!

Connecticut / Silver Lane

Silver Lane cottage

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Child Friendly

Price per night from

$292

Responds fast!
avg. 10 minutes

Price per night from

$292

Distance approx 8.92 km from Fairfield

(1) Excellent 

16

#2 - Your own place on the Beach near Silver Sands Park

Connecticut / Silver Lane

Silver Lane apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Private garden

Price per night from

$258

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$258

Distance approx 9.25 km from Fairfield

26

Cozy Milford Cottage w/ Fire Pit & Private Beach!

Connecticut / Milford

Milford cottage

4 7 min stay varies

  • 4 bedrooms
  • sleeps 7
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$338

Responds fast!
avg. 10 minutes

Price per night from

$338

Distance approx 18.34 km from Fairfield

(1) Excellent 

22

Little House By the Sea

Connecticut / New Haven

New Haven house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$316

Price per night from

$316

Distance approx 12.34 km from Fairfield

18

Stay at the beach/ one apartment w/ two bedrooms

Connecticut / Milford

Milford apartment

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
  • Nearest beach 25 mi
  • Child Friendly
  • Air conditioning

Price per night from

$149

Price per night from

$149

Distance approx 17.93 km from Fairfield

15

LUXURY COTTAGE

Westchester County / Pound Ridge

Pound Ridge cottage

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Ask about children
  • Ask about pets

Price per night from

$316

Responds fast!
avg. 2 hours 6 minutes

Price per night from

$316

Distance approx 19.83 km from Fairfield

(10) Excellent 

19

Jamaica Court Cottage

Connecticut / New Haven

New Haven house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Child Friendly
“Very nice!” We stayed 2 weeks in this beautiful house near the see. The owner is a fantastic host, attentive but never intrusive. Very quiet neighborhood. Perfect for a family with 2 kids. Good location. Great place to stay!!
…see more

Price per night from

$77

Price per night from

$77

Distance approx 14.9 km from Fairfield

12

Beautiful Waterfront Home with private beach

Long Island / East Setauket

East Setauket house

5 10 21 nights min

  • 5 bedrooms
  • sleeps 10
  • 21 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Child Friendly

Price per night from

$1,129

Price per night from

$1,129

Distance approx 17.97 km from Fairfield

21

Global Luxury Suites at Downtown Stamford

Connecticut / Stamford

Stamford apartment

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$206

Responds fast!
avg. 22 minutes

Price per night from

$206

Distance approx 7.14 km from Fairfield Show on Map

16

WESTPORT, CT - Overlook Ocean Beach; 1 hr to NYC

Connecticut / Westport

Westport house

4 6 7 nights min

  • 4 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary

Price per night from

$1,133

Responds fast!
avg. 26 minutes

Price per night from

$1,133

Distance approx 9.08 km from Fairfield

42

Spectacular Modern Home Near NYC

Connecticut / Weston

Weston house

5 8 2 nights min

  • 5 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$1,029

Responds fast!
avg. 1 hour 49 minutes

Price per night from

$1,029

Distance approx 8.92 km from Fairfield

18

#1 - A beach place by Silver Sands Park

Connecticut / Milford

Milford apartment

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Private garden

Price per night from

$259

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$259

Distance approx 19.8 km from Fairfield

67

Cosey Beach House

Connecticut / East Haven

East Haven house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Private garden

Price per night from

$575

Price per night from

$575

Distance approx 3.68 km from Fairfield Show on Map

26

Luxury Executive Estate 1 Hr from New York City

Connecticut / Easton

Easton house

6 20 2 nights min

  • 6 bedrooms
  • sleeps 20
  • 2 nights min
  • Nearest beach 10 mi
  • Child Friendly

Price per night from

$919

Responds fast!
avg. 1 hour 49 minutes

Price per night from

$919

Distance approx 7.11 km from Fairfield Show on Map

10

COZY CAPE

Connecticut / Westport

Westport house

3 4 1 night min

  • 3 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Ask about pets

Price per night from

$411

Price per night from

$411

Distance approx 16.05 km from Fairfield

24

Victorian Newtown Apt w/Fire Pit 20 Mi to Jennings

Connecticut / Newtown

Newtown apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Ski

Price per night from

$161

Responds fast!
avg. 24 minutes

Price per night from

$161

Distance approx 15.09 km from Fairfield

27

Apartment in great location, suburban

Connecticut / Seymour

Seymour house

1 6 3 nights min

  • 1 bedroom
  • sleeps 6
  • 3 nights min
  • Nearest beach 4 mi
  • Child Friendly
  • Air conditioning

Price per night from

$89

Responds fast!
avg. 1 hour 31 minutes

Price per night from

$89

Distance approx 17.59 km from Fairfield

34

Global Luxury Suites on Prospect Street

Connecticut / Stamford

Stamford apartment

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$234

Responds fast!
avg. 22 minutes

Price per night from

$234

Distance approx 7.43 km from Fairfield Show on Map

5

Adorable Guest Cottage

Connecticut / Weston

Weston cottage

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly

Price per night from

$178

Price per night from

$178

Distance approx 18.88 km from Fairfield

(3) Very Good 

21

Serene Connecticut Retreat - Luxury 2 bedroom apt

Connecticut / Stamford

Stamford apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ask about children
  • Car not necessary
  • Air conditioning

Price per night from

$212

Responds fast!
avg. 1 hour 29 minutes

Price per night from

$212

Distance approx 17.97 km from Fairfield

21

Global Luxury Suites at Downtown Stamford

Connecticut / Stamford

Stamford apartment

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$217

Responds fast!
avg. 22 minutes

Price per night from

$217

Distance approx 8.84 km from Fairfield Show on Map

13

New modern house near the water

Connecticut / Westport

Westport house

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Nearest beach 9 mi
  • Child Friendly
  • Air conditioning

Price per night from

$460

Price per night from

$460

Distance approx 17.59 km from Fairfield

(1) Average 

29

Global Luxury Suites on Prospect Street

Connecticut / Stamford

Stamford apartment

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$160

Responds fast!
avg. 22 minutes

Price per night from

$160

Distance approx 19.76 km from Fairfield

40

The Hobbit House- Yale and Beaches

Connecticut / East Haven

East Haven house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 0.2 mi
  • Child Friendly
  • Air conditioning

Price per night from

$173

Price per night from

$173

Distance approx 12.02 km from Fairfield

17

Global Luxury Suites near The Connecticut Post Mall

Connecticut / Milford

Milford apartment

2 5 10 nights min

  • 2 bedrooms
  • sleeps 5
  • 10 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$228

Responds fast!
avg. 22 minutes

Price per night from

$228

Distance approx 4.42 km from Fairfield Show on Map

39

Westport "Gold Coast" across from Southport beach

Connecticut / Southport

Southport cottage

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$230

Price per night from

$230

Distance approx 19.28 km from Fairfield

(8) Excellent 

34

WATERFRONT BEACH HOUSE - SOUND BEACH

Long Island / Sound Beach

Sound Beach house

3 10 3 nights min

  • 3 bedrooms
  • sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$539

Price per night from

$539