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Compare 268 Vacation Homes in Cheshire with updated reviews, rates, and availability.

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
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
9.4 out of 10, Exceptional, (10)
"Beautiful condo as advertised, great communication."
The price is AED 558
AED 1,053 total
includes taxes & fees
24 Sep - 25 Sep
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Trout Brook Trail 2 · Sprawling Classic New England Home
10.0 out of 10, Exceptional, (15)
"We had a great time in the home. My family of 5 stayed to explore the area. We were central to everything. There was a slight delay entering the property that was resolved very quickly and with no issue. Mark was very responsive. The home itself was very acclectic and fun. We felt very comfortable there. It was also stocked with many thoughtful items such as bottled water, ear plugs, books, etc. to help make our stay comfortable. It was a short walk to several blocks of amenities in West...
Trout Brook Trail 2 · Sprawling Classic New England Home
NEW-Another Fun Downtown Location 1st floor
2.0 star property
10.0 out of 10, Exceptional, (2)
"I was fairly new to VRBO, host helped alot with some things I missed (thanks!), and I am sure that was a hassle for him. He was very responsive, I met him and he is very invested in doing well. The house is nice, roomy, wifi had no issues, window AC in every room, surprisingly quiet (AC was on), ample parking. Bathroom is small. Great coffee shops etc. short walk across the street."
NEW-Another Fun Downtown Location 1st floor
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
Cozy newly remodeled home close to major amenities in Connecticut a
8.2 out of 10, Very Good, (15)
"We came to ct from South Carolina for my nieces wedding. E didn’t know what to expect. When we got there we were pleasantly surprised. The house was clean had a little fenced in patio. Check in was easy. Had easy access to the highway. The only thing I wish was that it had a first floor bathroom. But the house was perfect. Thank you. "
Cozy newly remodeled home close to major amenities in Connecticut a
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
9.8 out of 10, Exceptional, (112)
"Property was as described, perfect stay, beautiful home and perfect view. Had everything you could ever want and owner was very accommodating to our dogs."
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
10.0 out of 10, Exceptional, (5)
"To say that the property was in pristine condition and impeccably designed and decorated would be understatements. Everything was perfect and if we could have stayed in this luxurious home longer, we would have. The property was a perfect launching point for our visit to Powder Ridge for mountain biking and to visit other nearby sites in the beautiful area. The host responded to inquiries without delay and was a pleasure to interact with. We highly recommend without hesitation!"
The price is AED 2,204
AED 3,133 total
includes taxes & fees
24 Sep - 25 Sep
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Grammy's Lake House w/ Private Waterfront Access
10.0 out of 10, Exceptional, (6)
"Had a very good time We enjoyed the front porch"
Grammy's Lake House w/ Private Waterfront Access
Cozy Lakefront Bungalow w firepit/dock/kayaks
10.0 out of 10, Exceptional, (23)
"This is our second time visiting the area and staying at this beautiful home. It's close to many activities for children and adults, easy to access food and services and a beautiful overall area and home. We truly enjoy visiting!"
Cozy Lakefront Bungalow w firepit/dock/kayaks
Home on the sound
8.8 out of 10, Excellent, (6)
"I really enjoyed staying here and the apartment was really nice. The only complaint I have is that there was a pair of underwear with poop stains in the dryer left. The silverware was also all dirty and sticky and had stains all over them"
Home on the sound
Cozy 2 bedroom home located minutes from downtown
9.6 out of 10, Exceptional, (21)
"This was my second stay here and it went very well, yet again. Alioune really knows how to take care of the guest and responds extremely quick to any questions that are sent. The place is great. Very close to everything you are going to need and has plenty of space. Very adequate number of bed/bathrooms. I can't say enough. I'll be staying here again when I'm traveling to New Haven. 5-stars."
Cozy 2 bedroom home located minutes from downtown
#29 - Modern 5 Bedroom/2 Bath
10.0 out of 10, Exceptional, (1)
"Beautiful home and well suited for a peaceful stay. Great neighborhood and a wonderful how. Would recommend the property to anyone."
The price is AED 804
AED 1,788 total
includes taxes & fees
26 Sep - 27 Sep
#29 - Modern 5 Bedroom/2 Bath
Near Yale 8 beds Gaming Room
The price is AED 2,020
AED 4,035 total
includes taxes & fees
30 Sep - 1 Oct
Near Yale 8 beds Gaming Room
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
Beautiful 3BR, Rare Find, Clean & Guest Favorite
2.0 star property
The price is AED 550
AED 1,179 total
includes taxes & fees
1 Oct - 2 Oct
Beautiful 3BR, Rare Find, Clean & Guest Favorite
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (123)
"Our stay was incredible! The property was gorgeous- even with the home owners on property we barely saw them. We had full, private access to the backyard space- beach, pool, hot tub, fire pit, etc- all to ourselves. The property was clean and inviting and we will definitely go back. Everyone was so friendly and the area is picturesque. "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
gorgeous victorian direct ocean front single family six bedroom, ten rooms
10.0 out of 10, Exceptional, (56)
"My family and I thoroughly enjoyed our getaway. The home is a perfect mix of modern amenities and antique charms. The outdoor areas are outstanding."
gorgeous victorian direct ocean front single family six bedroom, ten rooms
Seaside Serenity: Relaxation by Jacob's Beach
9.2 out of 10, Wonderful, (27)
"Very close to the beach (with large playground and splash pad) and a 15 minute walk to town. Comfy beds with nice linens and plenty of towels. Included beach towels and chairs as well as a beach wagon. Host very responsive. Have stayed there before and will stay there again! "
Seaside Serenity: Relaxation by Jacob's Beach
Cozy Modern Home
9.6 out of 10, Exceptional, (26)
"Very nice place, stay there for a couple of nights for a get together, plenty of room. Only problem was some of the cleaning supplies where locked away where we couldn’t access it so we had to bring a mop and other supplies."
Cozy Modern Home
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Other property types in Cheshire

New Haven Village Suites
3.0 star property
7.6 out of 10, Good, (1925)
"Excellent! Best kept secret in New Haven. My room was spacious. Lobby was beautiful and had coffee and breakfast. I would stay again, but you must have a car."
The price is AED 364
AED 405 total
includes taxes & fees
6 Oct - 7 Oct
New Haven Village Suites
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (123)
"Our stay was incredible! The property was gorgeous- even with the home owners on property we barely saw them. We had full, private access to the backyard space- beach, pool, hot tub, fire pit, etc- all to ourselves. The property was clean and inviting and we will definitely go back. Everyone was so friendly and the area is picturesque. "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Luxury Furnished Apartments by Hyatus Downtown at Yale
3.5 star property
10.0 out of 10, Exceptional, (28)
"Great appartment, well stocked and ready excellent for our trip to visit family "
Luxury Furnished Apartments by Hyatus Downtown at Yale
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.