Weston Vacation Rentals

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Browse Select Weston Vacation Homes

Business or Weekend escape
Pool
Business or Weekend escape
9.6 out of 10, Exceptional, (22)
"Quaint basement studio with personal touches"
The price is CA $101
CA $181 total
includes taxes & fees
Oct 1 - Oct 2
Business or Weekend escape
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
On the beach, sun loungers
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (64)
"The good: We had a great time staying here. The first and second floor are beautiful and very well maintained. Both bathrooms and three bedrooms are very clean and have more than enough bath and beach towels. The fire pit and kayaks are also a great touch. The water is just steps away and the view is excellent. Just be sure to bring your own propane and firewood. What could be better? Communication with the host left a lot to be desired. I’m still not sure who runs the property. There are two...
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Lakeside luxury: beautiful, relaxing 4 bedroom home
Property grounds
Lakeside luxury: beautiful, relaxing 4 bedroom home
10.0 out of 10, Exceptional, (13)
"This house was perfect for my group of 6 college friends. We hadn't gotten together in over 10 years and wanted to relax and catch up. The furniture and bedding were extremely comfortable, the kitchen had everything we could possibly need and more! Very spacious home with off-street parking for 6 cars. We loved it here!!! "
Lakeside luxury: beautiful, relaxing 4 bedroom home
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Terrace/patio
Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, (111)
"Property was perfect for our family. Gym, steam shower, and theatre room were all amazing. Effortless check in/check out process. Gorgeous home and neighborhood. Communication with our host Chris was easy and fast. Thank you for everything:) "
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Lakeview Estate - Chef's Kitchen - NYC Getaway
Outdoor dining
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, (21)
"Great stay for 50th birthday "
Lakeview Estate - Chef's Kitchen - NYC Getaway
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
On the beach, sun loungers, beach towels
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
10.0 out of 10, Exceptional, (111)
"Had a quick work trip and wish we stayed longer! "
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Outdoor dining
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
10.0 out of 10, Exceptional, (40)
"We had such a great time! The views are stunning and the house has everything you need to enjoy your stay. The host Kerry was so helpful; we had a small issue with the shower and she had a plumber over within the hour to resolve it. Can’t wait to come back next summer! "
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Family-Friendly, Near-NYC Norwalk Retreat
Fridge, microwave, oven, stovetop
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 CA $236
CA $692 total
includes taxes & fees
Oct 9 - Oct 10
Family-Friendly, Near-NYC Norwalk Retreat
Spacious 4-BR house in lake community with beach access and swim-in-place spa.
Fridge, microwave, oven, stovetop
Spacious 4-BR house in lake community with beach access and swim-in-place spa.
2.0 star property
Spacious 4-BR house in lake community with beach access and swim-in-place spa.
Cheerful 4 bedrooms residential house.
Fridge, microwave, dishwasher, electric kettle
Cheerful 4 bedrooms residential house.
9.8 out of 10, Exceptional, (20)
"My friends and I stayed in Bridgeport for a weekend of music, and we had a great experience here! The owners were responsive and the place was exactly what we needed"
Cheerful 4 bedrooms residential house.
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, (45)
"This house is beautiful and has everything you need, including a gorgeous view of the Sound. All communication was swift and easy. My family built some wonderful memories here this week!"
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Milford Oasis: 2BR, Wi-Fi, Near Walnut Beach
Fridge, microwave, oven, stovetop
Milford Oasis: 2BR, Wi-Fi, Near Walnut Beach
9.6 out of 10, Exceptional, (14)
"We loved our little cottage, it was a perfect size for us. The backyard was a great space for our grandkids to run around in, which was fun for them as well. It was close to family so we could easily have them over for the day. The owners were very kid an responded quickly to our questions also. We also met some of the neighbors who were a lot of fun too!"
Milford Oasis: 2BR, Wi-Fi, Near Walnut Beach
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Property grounds
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
10.0 out of 10, Exceptional, (12)
"The house is huge and is very well equiped. Owners are very responsive to any questions or issues. Wonderful stay for the family."
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Catch some Zzz at Black Rock Harbor
Exterior
Catch some Zzz at Black Rock Harbor
10.0 out of 10, Exceptional, (11)
"Loved this modernized beach cottage. Walking distance to food and Bev as well as the beach. Quiet neighborhood. Perfect stay. "
Catch some Zzz at Black Rock Harbor
The W at Wildemere Beach
Beach nearby
The W at Wildemere Beach
10.0 out of 10, Exceptional, (3)
"We enjoyed our stay at The W! The short walk to the beach was great! We loved the coffee maker and made delicious lattes each day! The kitchen was well equipped and the beds were comfortable."
The W at Wildemere Beach
Colonial steps from beach: 3BR, 2BA Oasis with Hot Tub
Interior
Colonial steps from beach: 3BR, 2BA Oasis with Hot Tub
Colonial steps from beach: 3BR, 2BA Oasis with Hot Tub
Historic Connecticut Home w/ Grill & Spacious Yard
Microwave, stovetop, dishwasher, coffee/tea maker
Historic Connecticut Home w/ Grill & Spacious Yard
10.0 out of 10, Exceptional, (2)
"House is even cooler than the pictures give it credit for. Beautiful and funky. We really enjoyed our stay!!"
Historic Connecticut Home w/ Grill & Spacious Yard
Beach Retreat
Fridge, microwave, oven, stovetop
Beach Retreat
2.0 star property
The price is CA $405
CA $522 total
includes taxes & fees
Oct 7 - Oct 8
Beach Retreat
Direct Beachfront Property On Long Island Sound
3 bedrooms, desk, WiFi, bed sheets
Direct Beachfront Property On Long Island Sound
10.0 out of 10, Exceptional, (28)
"Very comfortable home. Perfect for our grown family. We enjoyed the relaxed atmosphere, the beach and water views right outside the back steps. We set up our umbrellas and chairs, had fun using the kyack and paddle board. It was a wonderful and relaxing time together! Looking forward to it again next year."
Direct Beachfront Property On Long Island Sound
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
Fridge, microwave, oven, stovetop
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
10.0 out of 10, Exceptional, (15)
"We stayed at this unit for one week while our son participated at a camp at Sacred Heart University. This unit is located close to Fiarfield beaches - we brought our bikes and started each day with a ride to the ocean and dip in the water. It is also walking distance to restaurants and shops. The unit has everything you need to cook and is absolutely spotless! A big bonus was bringing our furry child (golden retriever). The manager is responsive and helpful. Highly recommend this unit!"
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
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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 Weston

Adorable 1-Bedroom Cottage in Weston, CT
Fridge, microwave, oven, stovetop
Adorable 1-Bedroom Cottage in Weston, CT
10.0 out of 10, Exceptional, (30)
"Very cozy cottage a little off the beaten path in Weston. Quiet & stocked with amenities for our comfort. The owner was helpful & responsive. If there was any drawback it would be helpful to air out the cottage as its an old building & investing in some new pillows would be appreciated by the next guests. Otherwise a great stay."
The price is CA $262
CA $408 total
includes taxes & fees
Oct 1 - Oct 2
Adorable 1-Bedroom Cottage in Weston, CT
Stamford Suites
Exterior
Stamford Suites
2.5 star property
6.8 out of 10, (747)
"It was more than i expected. "
The price is CA $205
CA $236 total
includes taxes & fees
Oct 10 - Oct 11
Stamford Suites
Business or Weekend escape
Pool
Business or Weekend escape
9.6 out of 10, Exceptional, (22)
"Quaint basement studio with personal touches"
The price is CA $101
CA $181 total
includes taxes & fees
Oct 1 - Oct 2
Business or Weekend escape
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.