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Compare 293 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 177
SAR 386 total
includes taxes & fees
24 Dec - 25 Dec
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, (115)
"Enjoyed the theater room and the comfortable bed"
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Family XMas Bliss: Tree, Cozy Fireplace & Hot Cocoa
Living area

Family XMas Bliss: Tree, Cozy Fireplace & Hot Cocoa

10.0 out of 10, Exceptional, (10)
"This home is charming and what a surprise to see a Christmas tree set up! Our family spent Thanksgiving at this perfectly updated home. The home was very clean, functional and the kitchen was well stocked. I would not hesitate to recommend this home."
The price is SAR 710
SAR 1,815 total
includes taxes & fees
13 Jan - 14 January 2025
Family XMas Bliss: Tree, Cozy Fireplace & Hot Cocoa
Cheerful 4 bedrooms residential house.
Exterior

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (25)
"Great communication and accommodations from the host. We were in town for a concert and the location couldn't have been better! Would recommend this stay for anyone looking within the area."
Cheerful 4 bedrooms residential house.
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, (62)
"This home had everything you could ask for. It was very cozy and the owner has put very thoughtful touches into the property. Would definitely stay again!"
Adorable Cottage with Water Views, Across the street from Prime & other eateries
Waterview House Walking Distance from Cove Beach
Sunbathing lounge chairs

Waterview House Walking Distance from Cove Beach

9.0 out of 10, Wonderful, (16)
"The house is beautiful, amazing views! Communication was punctual."
The price is SAR 1,965
SAR 3,811 total
includes taxes & fees
16 Jan - 17 January 2025
Waterview House Walking Distance from Cove Beach
New Beach Home near Stamford Downtown/Shippan
Open concept living/dining room

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (16)
"Exactly as advertised, great location, easy check-in, hosts responded immediately to questions. Recommended."
New Beach Home near Stamford Downtown/Shippan
Bright Milford Beach House w/ Outdoor Shower
Milford Vacation Rental | 2BR | 2.5BA | Stairs Required | 1,450 Sq Ft

Bright Milford Beach House w/ Outdoor Shower

9.4 out of 10, Exceptional, (6)
"Cute place right across from the beach. Had everything that you need to cook, even a vegetable garden with fresh tomatoes. Comfortable and clean. The beach access is across the street,. "
Bright Milford Beach House w/ Outdoor Shower
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
Dining

Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

9.8 out of 10, Exceptional, (17)
"This place was super clean and exactly as described. "
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
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, (53)
"Cute, well-appointed house, great communication, fun stay!"
The price is SAR 902
SAR 1,766 total
includes taxes & fees
20 Jan - 21 January 2025
Captain's Cottage - Cold Spring Harbor Water Views
Stay 3 Nights or Longer Until January 31 and Get 15% Off
Cottage at Sunny Day, multiple levels for multiple views of the lake

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

9.8 out of 10, Exceptional, (29)
"The place has stunning views from just about every window. Taunton Lake is so serene and the surrounding area has so much local charm. The beds were comfy and the amenities were abundant. I hope to be back again someday."
Stay 3 Nights or Longer Until January 31 and Get 15% Off
Lakeview Estate - Chef's Kitchen - NYC Getaway
Outdoor dining

Lakeview Estate - Chef's Kitchen - NYC Getaway

9.8 out of 10, Exceptional, (24)
"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
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
Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!
Exterior

Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!

10.0 out of 10, Exceptional, (11)
"This was just what we were looking for. The house was roomy, open and charming. It was also relaxing to sit on the back deck surrounded by trees and listening to the calming sound of the brook. It felt like you out in the countryside yet the cute village of Sandy Hook along with Newtown restaurants and shopping were less than 10 minutes away."
Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!
"Milford Gem: 2BR, Wi-Fi, Walk to Walnut Beach "
Discover the essence of coziness in every corner of our charming house

"Milford Gem: 2BR, Wi-Fi, Walk to Walnut Beach "

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...
"Milford Gem: 2BR, Wi-Fi, Walk to Walnut Beach "
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...
Living area

Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...

9.2 out of 10, Wonderful, (5)
"It’s nice to have a place for our family of 5 that actually fits us all. Plenty of space and very clean. Thanks "
The price is SAR 785
SAR 1,763 total
includes taxes & fees
5 Jan - 6 January 2025
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...
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.
Charming duplex with private yard. Close to the beach, dining & shopping!
Living area

Charming duplex with private yard. Close to the beach, dining & shopping!

9.8 out of 10, Exceptional, (36)
"Duplex unit was clean, as described and perfect for our stay visiting family in Rye. Lots of extra towels and nice welcoming snacks in the kitchen. Super convenient location. Will likely stay there again. "
Charming duplex with private yard. Close to the beach, dining & shopping!
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!
Historic Hideaway with Lake Access!
Living area

Historic Hideaway with Lake Access!

9.6 out of 10, Exceptional, (12)
"Overall, very nice historic home. Very clean, perfect location for our family holiday, wonderful mattresses on all beds, well stocked kitchen with all cooking necessities. Good communication with owners who promptly helped to rectify a few issues. Would recommend to anyone looking to stay in this area."
Historic Hideaway with Lake Access!
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 1,841
SAR 2,653 total
includes taxes & fees
24 Dec - 25 Dec
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, (68)
"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.