House holiday rentals in Westport

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Popular amenities for Westport house rentals

House rentals with a pool

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

Once a Pond - time and stress slow down.

ShivaRating, 5 stars1 month ago
Spacious home with a nice outside area. Enjoyed coffee with birds and bunnies. Will stay here again.
Top Guest favourite
Home in Cheshire
5 out of 5 average rating, 135 reviews

Pool House

CindyRating, 5 stars1 month ago
The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!
Guest favourite
Home in Commack
4.99 out of 5 average rating, 140 reviews

GOOD VIBEZ HOUSE! Mini Golf-Pool-Hot Tub-GameRoom!

AliceRating, 5 stars3 weeks ago
We liked how easy it was to punch the code in to get into the home. Once in the home, it was really nice to see the welcome placard. We enjoyed access to robes, skincare, slippers, towels, etc. The game room was loads of fun. The indoor and outdoor ping pong tables were fun. We enjoyed billiards, arcade games and table games. The icing on the cake were the hot tub, the four mode shower and bidet. The Smart Home technology took a little getting used to, but it was very convenient once we did. We love the quick response time whenever we had a question or concern. This place allowed for a rejuvenating relaxing atmosphere and we are so glad that we chose “The Good Vibes” home for our debut AirBNB experience. Thanks again for hosting us in your charming abode!
Guest favourite
Home in Manorville
4.98 out of 5 average rating, 255 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

SolomonRating, 5 stars1 month ago
This Home was Amazing!! Anastasia is Phenomenal, I could see why they are Super Hosts. Their home is Beautiful and very clean. It’s filled with amenities! all that are in the description. So much so we didn’t even get a chance to take advantage of them all. We were only there for two days. Next time it’ll be much longer. I love this place!
Guest favourite
Home in Redding
4.88 out of 5 average rating, 16 reviews

Meeker Hill House - Country Escape w/ Heated Pool

RoryRating, 5 stars8 months ago
Our stay was stunning. The location is quiet and peaceful yet close enough to the town to get what you may need. The home itself is absolutely gorgeous. It’s clean, the layout is beautiful, and the views are out of this world. A truly incredible place to stay. The beds were very comfortable, the kitchen was perfect, and each room has a full bath which was great for our family. Overall highly recommend
Guest favourite
Home in Port Jefferson
4.92 out of 5 average rating, 125 reviews

Port Jefferson Convenient, Cozy and Chic!

DaleRating, 5 stars1 week ago
We we’re going to Port Jefferson for a family wedding. Our Airbnb was perfectly situated. There is a pool area that we never used because we just didn’t have time. But it looked very inviting. The town of Port Jefferson had plenty of nice restaurants and shops. This house was perfect for our situation. We had six adults, all family members.
Guest favourite
Home in Englewood
4.94 out of 5 average rating, 157 reviews

Englewood NJ Country Carriage House (15 min NYC)

MohamedRating, 5 stars3 weeks ago
Rating: ⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐ (10/10) Review: The house was amazing, especially the pool, sauna, and steam room. A truly exceptional experience in every detail. Thank you, Ms. Lise, for your warm hospitality!
Guest favourite
Home in Westhampton Beach
4.93 out of 5 average rating, 149 reviews

Hampton's Haven

DavidRating, 5 stars2 weeks ago
Esther is hands down one of the finest hosts we have had, and her house is beautiful and was spotless upon arrival and everything worked from pool to hot tub to grill etc... Area is very quiet. great place to relax with a mature group of friends or with your family. Esther was always responsive. Me and my crew have been renting houses for over three decades (Way before AirBnB). Esther is at the top of the list hands down. Thank you for everything. Will 1000% be back. ANd you shuld rent there too. You will not be disappointed.

Weekly house rentals

Top Guest favourite
Home in Fairfield
5 out of 5 average rating, 47 reviews

5 Minute Walk to Beach & Downtown Fairfield

LindseyRating, 5 stars6 days ago
This home is beautifully decorated and cozy. Peter was very accommodating and communicative. Very easy trip and would stay here again.
Top Guest favourite
Home in Norwalk
4.95 out of 5 average rating, 22 reviews

Family friendly

ColbyRating, 5 stars2 days ago
Excellent space for our group - easy to get in & out, had everything we needed, & plenty of room.
Guest favourite
Home in Fairfield
4.97 out of 5 average rating, 68 reviews

Modern Beach Bungalow

AmyRating, 5 stars1 month ago
Megan was wonderful flexible and saved us from a yucky hotel stay! He place is immaculate and comfortable and a quick walk to a peaceful little beach.
Guest favourite
Home in Easton
5 out of 5 average rating, 29 reviews

Historic Designer City Getaway

FayRating, 5 stars3 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.
Superhost
Home in Fairfield
4.81 out of 5 average rating, 126 reviews

Southport Shoreline Charm: Elegant Coastal Escape

KaraRating, 5 stars1 month ago
Perfect for SHU graduation. 10 mins from Amphitheatre and close enough to the college. Drew was very responsive answered my inquiries within minutes. House was spacious, comfortable and had everything we needed for a long weekend. As others have noted it is very close to the highway. The first night we notice the noise when going to bed but soon it was white noise and the remaining nights we did not even notice it. Best part of the long weekend was our dog got to join us.
Top Guest favourite
Home in Milford
4.98 out of 5 average rating, 53 reviews

Luxe Beach House | 3 Bd-King | Chef Kitchen | 4 TV

KristenRating, 5 stars6 days ago
Highly recommend this home! We had 5 adults and is a fantastic spot for a family vacation! Lots to do with access to cedar beach and walking trails as well as a very short ride to a local restaurants! House was spotless and owners were very responsive we had prior and during the trip, checking in to make sure we didn’t have any issues!
Top Guest favourite
Home in Trumbull
5 out of 5 average rating, 36 reviews

Cozy, updated single family in Fairfield County

ZulmaRating, 5 stars2 months ago
Beautiful home would definitely rent again and recommend to family and friends. Thanks Jennifer.
Guest favourite
Home in Fairfield
5 out of 5 average rating, 18 reviews

Newly built beautiful home within steps from Beach

SuzanneRating, 5 stars1 week ago
Perfect place to stay for groups or large families. Everyone in our group was happy with the accommodations and I would recommend. Space seems a bit larger than what is pictured.

Private house rentals

Top Guest favourite
Home in Milford
5 out of 5 average rating, 91 reviews

HGTV renovation! Steps to shops & water | Firepit!

SamanthaRating, 5 stars1 day ago
It was a great stay! Beach was easy to get to and was perfect for young kids. Everything was super clean, especially the beds and linens. Host was very responsive and friendly. There were some kids toys and pack and plays which was super helpful! Rooms were spacious.
Top Guest favourite
Home in Black Rock
4.98 out of 5 average rating, 54 reviews

Stay at Black Rock Harbor

TheresaRating, 5 stars1 week ago
⸻ Great Stay in a Lovely Black Rock Neighborhood We really enjoyed our stay at 65 Calderwood Court. The house was clean, comfortable, and well-equipped with everything we needed. The kitchen had plenty of supplies, and the beds were cozy after a full day of exploring. The location was excellent, just a short walk to Seabright Beach and close to local shops and restaurants. Staying during Black Rock Day was a nice bonus; we could easily join in the festivities and then retreat to a quiet, comfortable home. Allie was responsive and made the check-in process smooth. Overall, a very pleasant experience, and we’d happily stay here again when visiting the area.
Superhost
Home in Norwalk
4.8 out of 5 average rating, 5 reviews

Private WHOLE HOUSE + Fenced Backyard+ Parking 4br

TomRating, 5 stars6 days ago
Andrea's house was perfect for our family! The house is recently updated and very spacious. It's a great place if you want to be a 5min drive to everything in Norwalk!
Top Guest favourite
Home in Danbury
4.98 out of 5 average rating, 96 reviews

Lakeview Estate - Chef's Kitchen - NYC Getaway

AizelRating, 5 stars2 months ago
This house was wonderful as I would definitely stay there again and recommend it to family and friends. The views from the balconies and windows were amazing! The house was absolutely beautiful and super clean. The location was secluded but still near shops and restaurants. We loved our stay!
Guest favourite
Home in Fairfield
4.91 out of 5 average rating, 23 reviews

Seaside Home - Walk to Beach & Marina

TalithaRating, 5 stars1 week ago
Modern, clean and comfortable home. Kitchen was well equipped. Excellent communication with host.
Top Guest favourite
Home in Woodmont
5 out of 5 average rating, 97 reviews

Oceanfront Retreat: Modern Beach House

ShannonRating, 5 stars2 weeks ago
We had a relaxing overnight with our two pups! The bay/sound area is so peaceful. Our dogs enjoyed swimming before the tide came in and we kayaked along the shoreline. The inside was stunning and had everything you needed and more! We door dashed lobster rolls from the Bonfire Grille nearby (10/10) and ended the night in the hot tub! Coffee on the sunny patio was a great perk, too! Thanks again!!
Top Guest favourite
Home in Putnam Valley
5 out of 5 average rating, 10 reviews

Dr. Ruth’s Serene Lake Retreat

EvanRating, 5 stars5 months ago
After using Airbnb for years now no other place was a perfect 10. The lake house was simply great. Not only the physical status but the follow up and generosity of the hosts where beyond. We didn’t want to leave.
Superhost
Home in Rowayton
4.78 out of 5 average rating, 9 reviews

Coastal Comfort in Rowayton, CT

FawziaRating, 5 stars1 month ago
The house was just as described and just as the photos show. Spotlessly clean. Comfortable beds, linens and pillows. Pretty neighborhood, and peaceful.

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

    40 properties allow pets

  • Rentals with a pool

    20 properties have a pool

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

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