
House holiday rentals in Westport
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Top-rated house rentals in Westport
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Westport house rentals
House rentals with a pool

3.5 Acres of Relaxation, Pool, & Cozy Charm

Private Hudson Valley Country Retreat

Private apartment

Bright Mid-Century Modern Retreat-90 min from NYC

Riverfront Cottage Retreat & Pool 35 mins from NYC

Meeker Hill House - Country Escape w/ Heated Pool

Port Jefferson Convenient, Cozy and Chic!

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton
Weekly house rentals

HGTV renovation! Steps to shops & water | Firepit!

Stay at Black Rock Harbor

Private WHOLE HOUSE + Fenced Backyard+ Parking 4br

Charming Riverview Home *Near Train & I-95

Coastal Comfort in Rowayton, CT

Private house, Walk to Beach, Train, Town, Theatre

Chic Historic Home w/Water View

Charming Westport Retreat
Private house rentals

❤️ Your Silvermine Hideaway, nestled in nature.

Bull Shark Bungalow-Walk to Beach, Pet Friendly

New build! 1 house from beach

Remodeled Cozy Country Cape

Lakeview Estate - Chef's Kitchen - NYC Getaway

Coastal Lifestyle

Fairfield’s Four bedroom Family Home

Dr. Ruth’s Serene Lake Retreat
Quick stats about house rentals in Westport
Total rentals
100 properties
Total number of reviews
1.2K reviews
Family-friendly rentals
90 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Destinations to explore
- Plainview Holiday rentals
- Long Island Holiday rentals
- East River Holiday rentals
- New York Holiday rentals
- The Hamptons Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Pocono Mountains Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Boston Holiday rentals
- Ocean City Holiday rentals
- Rentals with beach access Westport
- Rentals with a fire pit Westport
- Family-friendly rentals Westport
- Kid-friendly rentals Westport
- Rentals with pools Westport
- Pet-friendly rentals Westport
- Rentals with a washing machine and dryer Westport
- Rentals with a patio Westport
- Rentals with outdoor seating Westport
- Rentals with a fireplace Westport
- Fitness-friendly rentals Westport
- Beachfront rentals Westport
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- Times Square
- Bryant Park
- Madison Square Garden
- Empire State Building
- Columbia University
- Barclays Center
- Jones Beach
- Fairfield Beach
- Yale University
- MetLife Stadium
- Citi Field
- Yankee Stadium
- Rye Beach
- Gilgo Beach
- Central Park Zoo
- United Nations Headquarters
- Grand Central Terminal
- USTA Billie Jean King National Tennis Center
- Statue of Liberty
- Rockefeller Center
- Radio City Music Hall
- Bronx Zoo
- The Metropolitan Museum of Art
- Rye Playland Beach