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Compare 327 Vacation Homes in Weston with updated reviews, rates, and availability.

Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, (105)
"This is a fantastic property and host"
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Cozy Ocean Front Retreat with Private Beach!
10.0 out of 10, Exceptional, (3)
"Had a fabulous weekend at this beach cottage. Great location, extremely close to the water, coffee shop, ice cream shop, lobster rolls, boardwalk along the water and of course the beach! Milford is a hidden gem for summer vacation and I will definitely go back and stay in this beach home!!"
Cozy Ocean Front Retreat with Private Beach!
Ocean Front Beach House with Private Beach Access - Newly Renovated!
10.0 out of 10, Exceptional, (5)
"Great home, great location! Very clean and was perfect for a large family. Host was responsive. Need to fix child door locks on sliders if you're going with children, the tide gets high on the wall."
Ocean Front Beach House with Private Beach Access - Newly Renovated!
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Westport Beach Town Mid-Century Vibe Retreat - Pet friendly, walk to downtown shops & restaurants
Westport Beach Town Mid-Century Vibe Retreat - Pet friendly, walk to downtown shops & restaurants
Lakeside luxury: beautiful, relaxing 4 bedroom home
10.0 out of 10, Exceptional, (2)
"We stayed at the house with our adult children and grandchild. The house was very clean. The linens, towels were of high quality and clean, and the kitchen was very functional with new cooking and kitchen utensils, pots and pans. It had hardwood floors on main level and the house was not cluttered at all. The view from the living room and deck of the lake was so beautiful and a stress release for sure. The backyard was roomy and well maintained. The neighborhood was quiet. The owner/manager was...
Lakeside luxury: beautiful, relaxing 4 bedroom home
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
9.8 out of 10, Exceptional, (19)
"Our family enjoyed our stay at the Cottage during our recent visit to CT for our son's college graduation. The views of the lake from the living room, the deck and the patio with fire pit are great and very peaceful. The kitchen was nicely outfitted with everything needed to cook and prepare meals. The only drawback was that there were no closets or chest of drawers in the (2) basement bedrooms. There was no place to unpack and hang our clothes for the 4 days we were there; the only closet was...
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.
10.0 out of 10, Exceptional, (6)
"Great property, very clean and host was quick to reply. We were impressed with the amenities available (most places don’t have detergent, etc) and the view was amazing! We didn’t have time to go to the dock but it looked very nice! Wish we had time to stay longer. We will definitely try to stay there again for our next family event"
Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.
2BR Home with Fenced Backyard near Walnut Beach
9.6 out of 10, Exceptional, (11)
"I stayed for 4 nights while traveling for business. The location was ideal and I enjoyed being able to walk the beach boardwalk every night. The house had everything I needed, was clean and the host was very responsive. I would stay here again."
2BR Home with Fenced Backyard near Walnut Beach
Catch some Zzz at Black Rock Harbor
10.0 out of 10, Exceptional, (5)
"It was our first time staying in the Black Rock area, and we found the neighborhood to be absolutely charming. Our VRBO accommodations were ideal providing easy access to the Black Rock neighborhood and the towns of Fairfield, Southport, and Westport. We had a great visit!!"
The price is SAR 2,266
SAR 3,900 total
includes taxes & fees
5 Jul - 6 Jul
5 Raj. - 6 Raj.
Catch some Zzz at Black Rock Harbor
Business or Weekend escape
9.4 out of 10, Exceptional, (16)
"Well kept studio type with everything you need. A much better option than getting a hotel in Bridgeport and an uber to downtown is very cheap. Quick replies from the host."
The price is SAR 281
SAR 506 total
includes taxes & fees
25 Jun - 26 Jun
25 Jum. II - 26 Jum. II
Business or Weekend escape
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, (59)
"We had a lovely weekend stay for a quick family get-away. The main kitchen and living area has spectacular views onto the lake as does the deck where we spent most of our time. The lake is just across the very quiet street. The kitchen is incredibly well stocked, the host super responsive and the rooms very comfortable. We did not use the well equipped basement work-out and additional TV space but it looked great. Easy to get to grocery store, hikes, local attractions but honestly we just loved...
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
Luxury home filled with books and art, with great access. Sleeps up to thirteen.
Luxury home filled with books and art, with great access. Sleeps up to thirteen.
Private Renovated Home Convenient to Sacred Heart & Fairfield Universities
10.0 out of 10, Exceptional, (23)
"Jon the owner was extremely communicative in making sure our stay was a success! And he succeeded!! The home was immaculate and fully stocked. We were 2 couples staying over for a convention in a neighboring city, and the accommodations was exactly what we needed. Quiet neighborhood and shopping/eateries was conveniently nearby. There's no question we will stay hear again! Thank you Jon for a wonderful vacation rental experience! 5 stars plus!"
Private Renovated Home Convenient to Sacred Heart & Fairfield Universities
PREMIER BEACH HOUSE ~ Steps From The Beach And Restaurants
9.8 out of 10, Exceptional, (22)
"My wife and I recently stayed at this property in Milford, CT and it was wonderful. The home was cozy and the area quiet, letting us have a nice relaxing weekend away from the hustle and bustle of NYC. The space was clean and comfortable with multiple places for sitting and relaxing after a long day out in the sun! Would definitely recommend."
PREMIER BEACH HOUSE ~ Steps From The Beach And Restaurants
Charming West Haven Home - Walk to Beach!
9.2 out of 10, Wonderful, (5)
"It was a wonderful experience. Property was very nice and clean and safe. A+"
Charming West Haven Home - Walk to Beach!
Gorgeous NEW Candlewood Lake 4BR 2BA Direct Waterfront Home +Dock ~JUNE SPECIAL!
Gorgeous NEW Candlewood Lake 4BR 2BA Direct Waterfront Home +Dock ~JUNE SPECIAL!
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
10.0 out of 10, Exceptional, (16)
"Donna, the host, was absolutely wonderful. Very responsive. Cute beach bungalow. Very comfortable. Perfect for the three of us, 2 adults and 19 year old daughter. Would absolutely recommend."
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
10.0 out of 10, Exceptional, (12)
"Stayed at Coastal Retreat for a weekend visit with son who attends Fairfield University, brought both sets of parents and teen daughter (ages ranging 73-16), plenty of room and able to enjoy a wonderful family dinner with son even in attendance. Wonderful area, close walk to beach and easy to get to downtown Fairfield and university. Very clean and welcoming! Greg was wonderful to work with and answered any question we had that came up both prior and upon arrival. The only thing we would mention...
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
NAUTICAL FAIRYTALE BEACH HOUSE / ACROSS THE ROAD FROM THE BEACH,45 MIN TO NYC
10.0 out of 10, Exceptional, (11)
"Enjoyed the house and the location! Would stay again!"
NAUTICAL FAIRYTALE BEACH HOUSE / ACROSS THE ROAD FROM THE BEACH,45 MIN TO NYC
Cheerful 4 bedrooms residential house.
9.8 out of 10, Exceptional, (14)
"Everything was exactly as advertised! It was a comfortable stay even for a group of 8 and checkin/checkout were very smooth and easy!"
Cheerful 4 bedrooms residential house.
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See all available properties in Weston
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.

Other property types in Weston

Adorable 1-Bedroom Cottage in Weston, CT
10.0 out of 10, Exceptional, (27)
"This is a great place to stay to get away or host family coming in from out of town, which is what we did. Now they have a new home away from home nearby."
Adorable 1-Bedroom Cottage in Weston, CT
Stamford Suites
2.5 star property
6.8 out of 10, (727)
"We loved all the dining options that were just a few minutes walk from the hotel. The hotel is outdated but it was very clean and the suites were spacious. The staff was friendly and helpful. "
The price is SAR 686
SAR 768 total
includes taxes & fees
4 Jul - 5 Jul
4 Raj. - 5 Raj.
Stamford Suites
DUNE Fairfield Beach
3.0 star property
9.4 out of 10, Exceptional, (12)
"perfectly clean, quiet, great location "
The price is SAR 983
SAR 1,310 total
includes taxes & fees
26 Jun - 27 Jun
26 Jum. II - 27 Jum. II
DUNE Fairfield Beach
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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