Holiday houses in Westport

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Popular amenities for Westport holiday rentals

Stay near Westport's top sights

Compo Beach12 locals recommend
Sherwood Island State Park10 locals recommend
Calf Pasture Beach16 locals recommend

Other great holiday rentals in Westport

Guest favourite
Home in Fairfield
4.96 out of 5 average rating, 26 reviews

Once 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 reviews

Westport 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 reviews

Historic 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 reviews

Westport 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 reviews

Boho 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 reviews

Waterfront 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 reviews

Cozy 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 reviews

Main 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

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