Holiday rentals in Westport

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Popular amenities for Westport holiday rentals

Stay near Westport's top sights

Compo Beach46 locals recommend
Sherwood Island State Park43 locals recommend
bartaco71 locals recommend
Trader Joe's62 locals recommend
Stew Leonard's46 locals recommend
The Whelk27 locals recommend

Other great holiday rentals in Westport

Superhost
Flat in Downtown Stamford
4.83 out of 5 average rating, 6 reviews

Sunny 1BR Apartment

JoanRating, 5 stars3 months ago
Clean , modern apt. Very easy to navigate with the technology. Staff very friendly and helpful. A bit noisy on street outside with traffic. Will definitely rent again with URBY, but request a courtyard side unit
Guest favourite
Guest house in Southbury
4.93 out of 5 average rating, 318 reviews

Charming Guest Cottage with Modern Amenities

CarolineRating, 5 stars3 months ago
John’s place was the perfect respite for our multi-day stay! The clean and cozy space is perfectly situated close to trails and parks for our Australian shepherd, but only a short drive to all the shopping you’d need (e. g. ShopRite for groceries and necessities). We thoroughly enjoyed our stay and know you will too!
Guest favourite
Home in Beacon
4.92 out of 5 average rating, 97 reviews

Beacon 2BR house w/ backyard, easy walk to main st

SarahRating, 5 stars1 week ago
We stayed here for our wedding weekend and couldn’t have asked for a better experience! The house was cute, clean, and comfortable - exactly what we needed during such a busy and exciting time. We especially appreciated how close it was to everything; it made it so easy for us to get around without stress. Eva was wonderfully responsive and kind, answering any questions quickly and making sure we had everything we needed. It truly felt like a home away from home. We’re so grateful to have had such a great place to stay during such a special moment in our lives!
Guest favourite
Cottage in Norwalk
4.94 out of 5 average rating, 67 reviews

Seaside Serenity: 2B 1B, Patio,Near Beach

AdamRating, 5 stars6 days ago
We had a wonderful stay at the cabin. It was a perfect size for our family and our son had a great time playing in the yard and the playground right next door. Our hosts were super responsive the couple of times we needed something. We'll definitely be back!
Guest favourite
Home in Garrison
4.93 out of 5 average rating, 161 reviews

Hudson Valley Mountaintop Riverview

ChristopherRating, 5 stars2 weeks ago
Mahmoud's accommodation was more than we could have wished for, it was perfect and had the most incredible views of the Hudson River and surrounding mountains. Mahmoud was very responsive and was able to answer all of our questions and fulfill our requests. We highly recommend his home to anyone else that's interested and we would love to make a trip back sometime in the future!
Guest favourite
Cabin in Rocky Point
4.89 out of 5 average rating, 484 reviews

Great little place just for a couple

AllaireRating, 5 stars4 days ago
We had a great time staying with Marina. The space was so clean and the perfect size for two adults and our senior pup. The outdoor space was beautifully landscaped and the beach was only a 5 minute walk. We would definitely come back!
Guest favourite
Home in Yonkers
4.95 out of 5 average rating, 21 reviews

Sweet & cozy house

RhadaisisRating, 5 stars1 week ago
This AirBnB experience was wonderful! The home was beautiful and exactly as pictured. Everything from the homey decor to the modern updated kitchen and bathroom was more than I expected. The host provided everything we needed and then some. The extras were such a nice touch! I highly recommend this home and the host, Hilda! She was very responsive and very friendly. I would book this home again in a heartbeat!
Guest favourite
Home in Woodmont
4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

TheoRating, 5 stars3 months ago
we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!

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

  1. Airbnb
  2. United States
  3. Connecticut
  4. Fairfield County
  5. Westport