
Holiday houses in Westport
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Top-rated holiday rentals in Westport
Guests agree: these stays are highly rated for location, cleanliness and more.
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Popular amenities for Westport holiday rentals
Other great holiday rentals in Westport
Guest favourite

Home in Fairfield
4.96 out of 5 average rating, 26 reviewsOnce a Pond - time and stress slow down.
ShivaRating, 5 stars4 weeks ago
Spacious home with a nice outside area. Enjoyed coffee with birds and bunnies. Will stay here again.
Top Guest favourite

Home in Westport
5 out of 5 average rating, 28 reviewsWestport Beach Haven - Perfect Coastal Getaway
SophieRating, 5 stars1 week ago
Marina’s place in Westport was great. It’s 5 min driving distance from everything, and the house is clean and stocked. My family of 4 was very comfortable. Marina also went out of her way to help us secure a crib for our toddler, and had gorgeous (truly!) fresh flowers all over the house. Would definitely stay again.
Guest favourite

Home in Easton
5 out of 5 average rating, 29 reviewsHistoric Designer City Getaway
FayRating, 5 stars2 weeks ago
We thoroughly enjoyed our stay at this historic house. It is full of character: we especially loved the massive fireplace where meals were presumably prepared back when it was an inn in the 1700s. It is also ridiculously spacious and very well furnished and equipped for a group of 10: the dining table easily seats 10, there is ample comfortable seating in the living room (not to mention at least 3 other sitting rooms one could gather in), and 8 of us were simultaneously cooking in the kitchen without anyone bumping elbows. Cooking here is a dream: there is a 6-burner+grill stove, 2 ovens, and all the equipment you could want (including a KitchenAid stand mixer and Vitamix blender). Moreover, Carly was an excellent host: she was always quick to respond, her messages were clear, and she generously allowed us to stay an extra hour to make our timing work out well. We highly recommend this house and would love to return.
Guest favourite

Apartment in Westport
4.91 out of 5 average rating, 44 reviewsWestport CT, Hide-away!
BarbaraRating, 5 stars1 week ago
Loved my stay. Great location, very clean and quiet, and within easy distances to where I was in Westport. Really appreciate John’s quick responses to my questions and am looking forward to staying here on future visits to Westport!
Superhost

Home in Westport
4.67 out of 5 average rating, 3 reviewsBoho Chic Private Home in the Heart of Westport CT
ClaudiaRating, 5 stars3 weeks ago
Emma and Nick were so welcoming. The entire property has an amazing vibe and peaceful surroundings. The kitchen had all the basics needed. The rooms were very comfortable. You felt like you were in the country but we were a short drive to everything. The entire area was just very charming. Emma and Nick deserve a super host rating for sure.
Top Guest favourite

Guesthouse in Norwalk
5 out of 5 average rating, 20 reviewsWaterfront Getaway - Norwalk, CT
HillaryRating, 5 stars1 week ago
Loved our stay here! The apartment was very clean and comfortable, and had everything we needed. Excellent location - nice view and very walkable both to Sono and East Norwalk. Communication was easy and clear, thank you! Only thing I would note is that there is a flight of stairs to get to the entrance which was a little tricky with our luggage and stroller (we were traveling with a baby) - didn’t detract from how great our stay was, and would still book again despite that.
Top Guest favourite

Guest suite in Norwalk
5 out of 5 average rating, 35 reviewsCozy 1 Bd Private Entrance In-law Suite & Hot Tub
JenessaRating, 5 stars3 weeks ago
This place was amazing!!! Tatiana was a great host and allowed us to check in a little early. Everything was clean and decorated beautifully. I can see why this place is always booked, if you have the chance to stay here, do it!! I highly recommend!
Superhost

Home in Westport
4.75 out of 5 average rating, 4 reviewsMain Street Westport, walk to shops, dining, town
CatherineRating, 5 stars2 weeks ago
Perfect for our family to all stay together for a family wedding. Plenty of bedrooms and bath with nice open common space for hanging out together.
Quick stats about holiday rentals in Westport
Total rentals
130 properties
Total number of reviews
3K reviews
Family-friendly rentals
100 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Destinations to explore
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- Rentals with a washing machine and dryer Westport
- Fitness-friendly rentals Westport
- Beachfront rentals Westport
- Pet-friendly rentals Westport
- Rentals with a fireplace Westport
- Rentals with a patio Westport
- Rentals with outdoor seating Westport
- Kid-friendly rentals Westport
- Rentals with beach access Westport
- House rentals Westport
- Family-friendly rentals Westport
- Rentals with a fire pit Westport
- Rentals with pools Westport
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- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
- Jones Beach
- Fairfield Beach
- Yale University
- Rye Beach
- Citi Field
- MetLife Stadium
- Yankee Stadium
- Gilgo Beach
- United Nations Headquarters
- Rye Playland Beach
- Statue of Liberty
- USTA Billie Jean King National Tennis Center
- Rockefeller Center
- Bronx Zoo
- Central Park Zoo
- Radio City Music Hall
- The Metropolitan Museum of Art