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Compare 258 Vacation Homes in Cheshire with updated reviews, rates, and availability.

Charming 2-bedroom townhome
Room

Charming 2-bedroom townhome

2.0 star property
9.6 out of 10, Exceptional, (5)
"The home was beautiful and I would stay there again."
The price is SAR 394
SAR 636 total
includes taxes & fees
24 Nov - 25 Nov
Charming 2-bedroom townhome
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Pool

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (126)
"We stayed here for an anniversary weekend away and found the property and neighborhood to be amazing. We enjoyed the hot tub, pool and firepit and went kayaking in the afternoon. Enjoyed amazing sunsets from the deck; Adam gave us spot-on restaurant recommendations. I don't know if the supply of snacks is standard or an anniversary "special", but all in all this place was a wonderful find. Thank you!!"
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
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
Amazing Lakefront Property
Dining

Amazing Lakefront Property

9.8 out of 10, Exceptional, (23)
"Great views and a good central location for day trips 👌. "
Amazing Lakefront Property
Tranquil Litchfield Connecticut Retreat".
Terrace/patio

Tranquil Litchfield Connecticut Retreat".

9.6 out of 10, Exceptional, (7)
"Quick trip"
The price is SAR 826
SAR 1,189 total
includes taxes & fees
25 Nov - 26 Nov
Tranquil Litchfield Connecticut Retreat".
Lakefront Home, Close to Mt Southington!
Wolcott Vacation Rental | 3BR | 2BA | 1,176 Sq Ft | Stairs Required

Lakefront Home, Close to Mt Southington!

10.0 out of 10, Exceptional, (13)
"Staff very much enjoyed the atmosphere after long days of work. Wonderful Ownership. Thank you so much Susan!"
Lakefront Home, Close to Mt Southington!
Cozy Modern Home
Exterior

Cozy Modern Home

9.6 out of 10, Exceptional, (30)
"The house was clean, updated and well kept. We went on a guys hiking trip this house worked out perfectly for us. "
Cozy Modern Home
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Living Room

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (18)
"So glad we found this property to accommodate our family of six for the weekend. It was cozy, updated and immaculately clean. The owners seem to have thought of everything and clearly care about providing an exceptional experience. Highly recommend!"
Charming 3BR Hilltop House, Newly Remodeled with Arcade
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Exterior

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

10.0 out of 10, Exceptional, (2)
"Started with Kristine greeting us as we drove in. Was accommodating to our requests and was very quick to reply to our few messages. Clothes dryer is very small. Short walk to a great park and beach."
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Living area

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

9.6 out of 10, Exceptional, (11)
"Very nice and clean family was visiting my daughter at the University of New Haven was also very close "
The price is SAR 544
SAR 1,047 total
includes taxes & fees
25 Nov - 26 Nov
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
McAngel Haven: 5 mins from Yale
Spaciously Stylish Living Area with Fireplace and Dining View

McAngel Haven: 5 mins from Yale

9.6 out of 10, Exceptional, (5)
"The house was perfect for a family of 4 and a couple! It’s a fairly quiet neighborhood so it was a good place to come back to relax each day. Parking for 2 cars was helpful and the coded entry was very easy. Nice setup and thoughtful features. Angela was very responsive and friendly! Definitely recommend!"
The price is SAR 822
SAR 1,984 total
includes taxes & fees
24 Nov - 25 Nov
McAngel Haven: 5 mins from Yale
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!
Home on the sound
Room

Home on the sound

8.6 out of 10, Excellent, (7)
"This was a greay stay and the property was really cute and cozy. It is an upstairs portion of a duplex "
Home on the sound
Cozy 2 bedroom home located minutes from downtown
Room

Cozy 2 bedroom home located minutes from downtown

9.6 out of 10, Exceptional, (23)
"We found this house to be the perfect spot just outside downtown New Haven. We did need a car, but the location was great. We had easy access to main roads, downtown, and there was sufficient local restaurants and stores for stocking the house. The unit was as it appeared and the host was responsive and helpful when needed."
Cozy 2 bedroom home located minutes from downtown
Gather your family at this country estate
Living area

Gather your family at this country estate

10.0 out of 10, Exceptional, (3)
"This is an older home with charm. Lots of room, and while just six of us stayed, it appears more could be accommodated with inflatable mattresses. We enjoyed sitting outside by the simple fire pit one night. I would encourage the owners to put an outside light in the back as I stumbled on the stairs twice but that’s really the only issue. We are so sorry we misplaced one of the two keys,please send us a bill for a copy if you don’t find it. Thank you!"
Gather your family at this country estate
Guilford home -self check in, off-street parking
Exterior

Guilford home -self check in, off-street parking

9.4 out of 10, Exceptional, (8)
"The property was nice, clean and comfortable. "
Guilford home -self check in, off-street parking
Near Yale 8 beds Gaming Room
Exterior

Near Yale 8 beds Gaming Room

The price is SAR 2,065
SAR 4,124 total
includes taxes & fees
1 Dec - 2 Dec
Near Yale 8 beds Gaming Room
NEW-Another Fun Downtown Location 1st floor
Exterior detail

NEW-Another Fun Downtown Location 1st floor

2.0 star property
10.0 out of 10, Exceptional, (6)
"This was our second stay at this VRBO and hope to stay again on return trips to the area."
NEW-Another Fun Downtown Location 1st floor
The Jewel of The Cove - Historic Coastal Retreat

The Jewel of The Cove - Historic Coastal Retreat

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is SAR 777
SAR 1,832 total
includes taxes & fees
8 Dec - 9 Dec
The Jewel of The Cove - Historic Coastal Retreat
Sunny East Haven Home w/ Grill: Walk to Beaches!
East Haven Vacation Rental | 4BR | 1.5BA | 1,520 Sq Ft | Stairs Required

Sunny East Haven Home w/ Grill: Walk to Beaches!

2.0 star property
10.0 out of 10, Exceptional, (3)
"6 of us stayed here for a music festival. The location, fantastic! Ocean views, check. The bedding, the furniture, kitchen supplies....no amenity was overlooked. Happened to meet owner when were checking in. He was great. Couldn't have been more accomodating. Great great place for a few nights or longer. Wush we were here longer. "
Sunny East Haven Home w/ Grill: Walk to Beaches!
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 Cheshire

New Haven Village Suites
Front of property

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (1966)
"Convenient location, helpful staff, comfortable bed. Thanks!"
The price is SAR 368
SAR 424 total
includes taxes & fees
24 Nov - 25 Nov
New Haven Village Suites
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Pool

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (126)
"We stayed here for an anniversary weekend away and found the property and neighborhood to be amazing. We enjoyed the hot tub, pool and firepit and went kayaking in the afternoon. Enjoyed amazing sunsets from the deck; Adam gave us spot-on restaurant recommendations. I don't know if the supply of snacks is standard or an anniversary "special", but all in all this place was a wonderful find. Thank you!!"
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Luxury Furnished Apartments by Hyatus Downtown at Yale
Room

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.8 out of 10, Exceptional, (34)
"Great location! Clean building And modern. "
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.