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Compare 288 Vacation Homes in Westport with updated reviews, rates, and availability.

Business or Weekend escape
A Queen Size Bed for Two Persons and Also Queen Size Sofa Bed for Two Persons.

Business or Weekend escape

9.6 out of 10, Exceptional, (30)
"Stayed for my other half bday. Place was clean and described well"
The price is SAR 300
SAR 528 total
includes taxes & fees
26 Nov - 27 Nov
Business or Weekend escape
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Exterior

Lower Lvl Private 2BR/1BA Family/Pet Friendly

10.0 out of 10, Exceptional, (114)
"Peaceful, lovely neighborhood. Easy access to country drives. Quick drive to Stamford station. Helpful host. "
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Beautiful historic home in Stony Brook!
Living area

Beautiful historic home in Stony Brook!

2.0 star property
9.2 out of 10, Wonderful, (5)
"This was our second stay at this charming cottage, perfect mix of colonial feel and modern amenities. Plenty of space for us and our dog. Everything we needed was included. Location is close to village and beach. "
Beautiful historic home in Stony Brook!
Lakeview Estate - Chef's Kitchen - NYC Getaway
Terrace/patio

Lakeview Estate - Chef's Kitchen - NYC Getaway

10.0 out of 10, Exceptional, (23)
"Fantastic place! Beautiful views, lots of room, comfy beds, clean. There was 10 of us and it was a delight. Highly recommend it. "
Lakeview Estate - Chef's Kitchen - NYC Getaway
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Interior

Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

10.0 out of 10, Exceptional, (46)
"The house was beautiful and a perfect place for our family to be at while visiting our daughter who is a student at Yale. We saw the sunrise over the ocean from our bedroom window. Wish we found this sooner!"
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail
Exterior

Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail

10.0 out of 10, Exceptional, (34)
"Our stay at Gersende's property was delightful. We had seven friends together for a wedding and this house and property served as a much appreciated comfortable and peaceful retreat. The pool was lovely, the kitchen was well-stocked and functional and the homes quirks and charm grew on us a little more each day. We walked to GrayBarns Mercantile every morning for coffee and it was a quick drive from the grocery as well as the PJ Glass House. Gersende was kind, easy to reach and incredibly...
Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail
Modern 2BR House w/ Fenced Yard & Wi-Fi
our inviting living room awaits, bathed in soft light and adorned with touches of homey charm

Modern 2BR House w/ Fenced Yard & Wi-Fi

9.6 out of 10, Exceptional, (16)
"We had a blast staying at this property. The attention to detail in the amenities provided was amazing. We travelled with our infant and there was a high chair, pack & play, and baby bath available for us to use, this was perfect so we didn’t have to worry about traveling with these items. Loved the toiletry boxes provided for shampoo, conditioner, laundry pods, dish soap, & more! The location was perfect! Nice short walk to the delicious Walnut Beach Creamery, Walnut Beach Coffee House, and...
Modern 2BR House w/ Fenced Yard & Wi-Fi
Stylish Beach Home near Stamford Downtown/Beach
Cozy backyard with fire pit and BBQ grill

Stylish Beach Home near Stamford Downtown/Beach

10.0 out of 10, Exceptional, (19)
"Lovely place, great location, had absolutely everything we needed! Would absolutely stay here again. "
The price is SAR 3,676
SAR 6,011 total
includes taxes & fees
24 Nov - 25 Nov
Stylish Beach Home near Stamford Downtown/Beach
Ocean Front Beach House with Private Beach Access - Newly Renovated!
Steps to the beach

Ocean Front Beach House with Private Beach Access - Newly Renovated!

10.0 out of 10, Exceptional, (12)
"We rented this house to celebrate my mother’s 80th birthday. The 6 of us had a great time. The house couldn’t be closer to the water. Beautiful house. Plenty of room for everyone. Get comfortable. Clean. Nice quiet street. Great host. Gave us games, towels, and there were more things in the garage that we didn’t even use. Weather wasn’t the best but we made the most of it. Water is very shallow for a long distance so you can easily walk out and hang around when the tide goes down. Overall...
Ocean Front Beach House with Private Beach Access - Newly Renovated!
The ARLO - Walk to Brewery and Restaurants
Living area

The ARLO - Walk to Brewery and Restaurants

10.0 out of 10, Exceptional, (1)
"Great proximity to restaurants graduation venue, Sacred Heart. We had a great time. The property is clean private, and really really cute."
The ARLO - Walk to Brewery and Restaurants
Family-Friendly, Near-NYC Norwalk Retreat
Cozy living room filled with art and entertainment

Family-Friendly, Near-NYC Norwalk Retreat

2.0 star property
10.0 out of 10, Exceptional, (2)
"Met all of our expectations, made a very enjoyable stay with 2 little ones. Host was accommodating and went above and beyond to support our needs. "
The price is SAR 962
SAR 2,287 total
includes taxes & fees
9 Dec - 10 Dec
Family-Friendly, Near-NYC Norwalk Retreat
Beautiful Hampton Long Island Family Getaway with Pool.
Property grounds

Beautiful Hampton Long Island Family Getaway with Pool.

7.6 out of 10, Good, (5)
"Had a great time here. The house was clean and well maintained. The host communicated with us often and overall it was a great stay!"
The price is SAR 3,567
SAR 6,110 total
includes taxes & fees
24 Nov - 25 Nov
Beautiful Hampton Long Island Family Getaway with Pool.
Cheerful 4 bedrooms residential house.
Exterior

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (23)
"Washer downstairs unavailable, thermostat only on request, feather pillows (allergy). Otherwise it was ok with plenty of bedrooms and baths. "
Cheerful 4 bedrooms residential house.
Captain's Cottage - Cold Spring Harbor Water Views
View Cold Spring Harbor in the Fall

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (52)
"The captain cottage was exactly what Mom and I wanted! Beautiful views of the bay,super easy five minute walk to the main street of Cold Spring Harbor, adorable house with everything you need, and Kim was on top of it every time we neededhelp. Thank you so much for hosting us and cannot wait to be back!"
The price is SAR 751
SAR 1,581 total
includes taxes & fees
4 Dec - 5 Dec
Captain's Cottage - Cold Spring Harbor Water Views
Adorable Cottage with Water Views, Across the street from Prime & other eateries

Adorable Cottage with Water Views, Across the street from Prime & other eateries

9.8 out of 10, Exceptional, (60)
"We enjoyed our short stay at the cottage! The thoughtful amenities were appreciated (especially ALL your coffee needs except dairy, toiletries, filtered water ready in the fridge), and there were probably more we didn’t take advantage of…we were only there for 3 days and didn’t cook in the house but noticed the pantry was stocked with spices and cooking essentials. The beds and bedding were very comfortable. The outdoor area was lovely and well maintained but we didn’t use it much because of...
Adorable Cottage with Water Views, Across the street from Prime & other eateries
2 mini-bedrooms apartment with antique bathtub.
Private kitchen

2 mini-bedrooms apartment with antique bathtub.

10.0 out of 10, Exceptional, (18)
"Conveniently located to small downtown area & train into NYC. "
2 mini-bedrooms apartment with antique bathtub.
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Front of the House, porch looking out on Long Island Sound

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (115)
"Spectacular views from the second floor balcony! very clean and spacious! Highly recommend staying here. "
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Terrace/patio

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

10.0 out of 10, Exceptional, (14)
"Beautiful property— even more than the pictures (which is often rare). Quiet, scenic, and spacious. Communication with the host was very good and helpful."
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home
Modern mid century guest house. Built in 1955 inside of old court

ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home

10.0 out of 10, Exceptional, (23)
"The property is absolutely stunning, very peaceful and Zen! Olga is fantastic very caring and attentive to detail. This was the perfect anniversary getaway and I can’t wait to go back."
ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home
Private Renovated Home Convenient to Sacred Heart & Fairfield Universities
Exterior

Private Renovated Home Convenient to Sacred Heart & Fairfield Universities

10.0 out of 10, Exceptional, (26)
"Jon is an excellent and very responsive host. His home is beautiful, very clean, well appointed, and organized. All the comforts of home are provided. This is our second time staying at this property and we will be back!"
Private Renovated Home Convenient to Sacred Heart & Fairfield Universities
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Westport

Westport Paradise With Every Amenity!
Guest house, and pool, as seen from the tennis court.

Westport Paradise With Every Amenity!

10.0 out of 10, Exceptional, (23)
"We had such a nice stay at Mark and Sarah’s. Check in was so easy and they were very attentive to anything we needed. The property and apartment are beautiful, it was so nice waking up and seeing all the trees and it was so quiet. We will definitely be back and stay when we are visiting our daughter at Fairfield."
The price is SAR 1,840
SAR 2,659 total
includes taxes & fees
24 Nov - 25 Nov
Westport Paradise With Every Amenity!
Studio OSM · Sunny Westport Studio Apt. Above Historic Mill

Studio OSM · Sunny Westport Studio Apt. Above Historic Mill

10.0 out of 10, Exceptional, (67)
"Can’t say enough good things about studio apartment! Gerard was wonderful and easy to communicate with. This apartment had absolutely everything we needed! The airline lost one of our bags, so the onsite washing machine was very much appreciated! We will definitely be back to stay here again!"
Studio OSM · Sunny Westport Studio Apt. Above Historic Mill
Stay 3 Nights or Longer Until January 31 and Get 15% Off
Enjoy the spacious lawn - an ideal retreat in this charming, quiet neighborhood.

Stay 3 Nights or Longer Until January 31 and Get 15% Off

10.0 out of 10, Exceptional, (3)
"After a rough year we were able to get a few days away and at the last minute chose this location. Everything we were looking for was there. The home and grounds were beautiful. The location in Westport was exactly what we wanted: magnificent fall foliage, quiet where the home was but close enough to walk to town and enjoy every aspect of being close by the town for lovely cafes and restaurants. Also, beautiful places were accessible by car in minutes such as Earthplace for trails and nature...
Stay 3 Nights or Longer Until January 31 and Get 15% Off
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.