Westport Vacation Rentals, Houses & More


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Areas near Westport

Great rentals within 20 miles that match your search

1 / 21

Serene Connecticut Retreat - Luxury 2 bedroom apt

  • 2
  • 4
  • 3 nights min

$201

Details

1 / 26

Huckleberry Quarters, a cozy Redding Retreat in a 1918 Farmhouse.

  • 1
  • 2
  • 1 night min

$95

Details

1 / 14

Beautiful Secluded Stone Country Home Close to NYC

  • 4
  • 8
  • 7 nights min

$286

Details

1 / 23

Luxurious Lake Front home

  • 3
  • 10
  • Min stay varies

$401

Details

1 / 7

New Contemporary Beach House

  • 3
  • 6
  • 7 nights min

$1001

Details

1 / 18

#1 - A beach place by Silver Sands Park

  • 2
  • 6
  • Min stay varies

$125

Details

1 / 8

Beach House

  • 3
  • 6
  • 2 nights min

$950

Details

1 / 17

Charming and immaculate 3 br duplex!

  • 3
  • 5
  • 4 nights min

$206

Details

1 / 37

Unique, Modern, & Private 3 bedroom on 6 acres

  • 3
  • 8
  • 3 nights min

$300

Details

1 / 5

3rd floor getaway

  • 1
  • 3
  • 1 night min

$99

Details

1 / 5

Adorable Guest Cottage

  • 2
  • 4
  • 1 night min

$155

Details

1 / 32

Elegant Home on an Acre of Rolling Lawns

  • 3
  • 10
  • Min stay varies

$600

Details

1 / 48

Large Home, Pool, Hot Tub on Several Acres

  • 4
  • 10
  • 1 night min

$526

Details

1 / 22

Centrally located. Near Greenwich Ave, Greenwich Train Station and Bruce Park.

  • 3
  • 8
  • 1 night min

$351

Details

1 / 16

Ground floor sunlit apt. in great area!

  • 1
  • 4
  • 1 night min

$85

Details

1 / 26

NEW! 4BR Milford Cottage with Private Beach!

  • 4
  • 7
  • Min stay varies

$295

Details

1 / 24

2BR Northport Home w/3 Private Decks&Harbor Views

  • 2
  • 4
  • Min stay varies

$125

Details

1 / 12

Beautiful Waterfront Home with private beach

  • 5
  • 10
  • 21 nights min

$986

Details

1 / 6

Private pool house with access to pool and tennis

  • 1
  • 2
  • 2 nights min

$125

Details

1 / 18

Charming Victorian with Pool and Water Views

  • 3
  • 5
  • 3 nights min

$326

Details

1 / 14

2BR House$169 walk to everything

  • 2
  • 4
  • 1 night min

$170

Details

1 / 16

We think it's better than the Hamptons.

  • 4
  • 10
  • 7 nights min

$286

Details

1 / 26

Quaint and immaculate 3 br duplex!

  • 3
  • 5
  • Min stay varies

$206

Details

1 / 8

Breathtaking water views, truly peaceful retreat!

  • 2
  • 4
  • 2 nights min

$196

Details

1 / 11

Private Room in Eclectic Downtown Stamford Loft

  • 1
  • 2
  • 2 nights min

$66

Details

1 / 16

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

  • 2
  • 4
  • 1 night min

$125

Details

1 / 39

Westport "Gold Coast" across from Southport beach

  • 1
  • 3
  • 2 nights min

$201

Details

1 / 42

Spectacular Modern Home Near NYC

  • 5
  • 8
  • 2 nights min

$895

Details

1 / 30

Elegant Home on an Acre of Rolling Lawns

  • 3
  • 10
  • Min stay varies

$701

Details

1 / 26

Luxury Executive Estate 1 Hr from New York City

  • 6
  • 20
  • 2 nights min

$701

Details

1 / 7

Luxury Direct Waterfront Beach Home

  • 2
  • 6
  • 4 nights min

$501

Details

1 / 14

Black Rock~ Fairfield County's hidden gem!

  • 2
  • 6
  • 30 nights min

$150

Details

1 / 25

Luxury Executive Estate 1 Hr from New York City ~ RA132911

  • 6
  • 12
  • Min stay varies

Inquire for Rates

Details

1 / 15

LUXURY COTTAGE

  • 1
  • 4
  • 2 nights min

$275

Details

1 / 20

3BR House $199 and up Half ACRE WALK 2 EVERYTHING

  • 3
  • 4
  • 1 night min

$249

Details

1 / 16

DIRECT WATERFRONT HOUSE--GREAT LOCATION AND VIEWS

  • 3
  • 6
  • Min stay varies

$434

Details

1 / 16

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

  • 4
  • 6
  • 7 nights min

$986

Details

1 / 10

COZY CAPE

  • 3
  • 4
  • 1 night min

$357

Details

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