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29 Houses

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

$987

Responds fast!
avg. 26 minutes

Price per night from

$987

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

$410

Price per night from

$410

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

$401

Price per night from

$401

Great rentals within 20 miles that match your search

Distance approx 16.23 km from Westport

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

$293

Responds fast!
avg. 15 minutes

Price per night from

$293

Distance approx 15.9 km from Westport

(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 19.31 km from Westport

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

$129

Price per night from

$129

Distance approx 16.23 km from Westport

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

$339

Responds fast!
avg. 15 minutes

Price per night from

$339

Distance approx 6.11 km from Westport

7

New Contemporary Beach House

Connecticut / Fairfield

Fairfield house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly

Price per night from

$1,147

Price per night from

$1,147

Distance approx 12.44 km from Westport

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

$276

Price per night from

$276

Distance approx 6.45 km from Westport

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

$1,026

Responds fast!
avg. 1 hour 49 minutes

Price per night from

$1,026

Distance approx 16.83 km from Westport

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

$1,131

Price per night from

$1,131

Distance approx 19.86 km from Westport

(4) Excellent 

16

Ground floor sunlit apt. in great area!

Long Island / Huntington

Huntington apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

Price per night from

$98

Responds fast!
avg. 3 hours 8 minutes

Price per night from

$98

Distance approx 11.19 km from Westport

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. 54 minutes

Price per night from

$206

Distance approx 18.45 km from Westport

(3) Very Good 

30

Quaint and immaculate 3 br duplex!

Connecticut / Greenwich

Greenwich house

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Nearest beach 2 mi
  • Child Friendly
  • Air conditioning

Price per night from

$224

Responds fast!
avg. 2 hours 38 minutes

Price per night from

$224

Distance approx 17.74 km from Westport

48

Large Home, Pool, Hot Tub on Several Acres

Westchester County / Mount Kisco

Mount Kisco house

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$860

Responds fast!
avg. 2 hours 22 minutes

Price per night from

$860

Distance approx 15.9 km from Westport

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

$258

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$258

Distance approx 16.37 km from Westport

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
  • Suitable for children age 5+

Price per night from

$140

Price per night from

$140

Distance approx 19.29 km from Westport

7

Luxury Direct Waterfront Beach Home

Connecticut / Milford

Milford house

2 6 4 nights min

  • 2 bedrooms
  • sleeps 6
  • 4 nights min
  • Child Friendly

Price per night from

$574

Price per night from

$574

Distance approx 6.86 km from Westport

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

$802

Responds fast!
avg. 1 hour 49 minutes

Price per night from

$802

Distance approx 11.19 km from Westport

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. 54 minutes

Price per night from

$217

Distance approx 10.81 km from Westport

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. 54 minutes

Price per night from

$234

Distance approx 5.82 km from Westport

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 18.45 km from Westport

(7) Excellent 

24

Charming and immaculate 3 br duplex!

Connecticut / Greenwich

Greenwich house

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Child Friendly
“Charming Byram Townhouse” Loved our stay in this lovely townhouse located in the Byram section of Greenwich - great access to major roadways, MetroNorth, shopping, restaurants - all that the area has to offer. The home is spotless and well outfitted -
…see more

Price per night from

$207

Responds fast!
avg. 2 hours 38 minutes

Price per night from

$207

Distance approx 12.05 km from Westport

(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 17.1 km from Westport

14

Beautiful Secluded Stone Country Home Close to NYC

Connecticut / Greenwich

Greenwich farmhouse

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$351

Responds fast!
avg. 2 hours 10 minutes

Price per night from

$351

Distance approx 10.81 km from Westport

(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. 54 minutes

Price per night from

$160

Distance approx 18.91 km from Westport

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. 38 minutes

Price per night from

$228

Distance approx 3.44 km from Westport

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 19.56 km from Westport

43

Centre Island Estate

Long Island / Oyster Bay

Oyster Bay house

6 50 min stay varies

  • 6 bedrooms
  • sleeps 50
  • min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child Friendly

Price per night from

$1,001

Price per night from

$1,001