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Cheshire Vacation Rentals

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Browse Select Cheshire Vacation Homes

Updated ranch Home 4 minutes from the beach on a quiet end street.
6.0 out of 10, 1 review
"Family of 5 (2 adults, 3 teens) stayed for long weekend. Friendly and fairly quick communication with Fabian was appreciated. House is approx 1 to 1.5 miles to Long Island Sound and beach. Nice and quiet neighborhood. The place was clean with exception of downstairs which had some of the owner's personal belongings strewn about. The biggest disappoint was no hot water or heat for most of the stay. Fabian offered hot showers at another nearby location and brought in a space heater which was...
Updated ranch Home 4 minutes from the beach on a quiet end street.
Ocean Front Beach House with Private Beach Access - Newly Renovated!
10.0 out of 10, Exceptional, 4 reviews
"We stayed here during my graduation weekend and really enjoyed having a space for the whole family to stay together and unwind in between all the hectic activities of the weekend. The house is right on the water and has plenty of bedrooms for everyone. It's a good, quiet location that is not too far from the highway and easy to get back and forth from New Haven. It's definitely worth staying here!"
Ocean Front Beach House with Private Beach Access - Newly Renovated!
Lakeside luxury: beautiful, relaxing 4 bedroom home
10.0 out of 10, Exceptional, 2 reviews
"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
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Beautiful 4BR Beach House with Private Beach Access.
10.0 out of 10, Exceptional, 65 reviews
"Visited family back in CT and this was the perfect place to stay. Kind of like a Tardis, it was bigger on the inside! Thank you!"
Beautiful 4BR Beach House with Private Beach Access.
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
9.8 out of 10, Exceptional, 106 reviews
"Very nice stay. Only disappointment was the lack of a hot tub. Otherwise a perfect venue for our group."
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, 1 review
"Beautiful new home and property! Would one back for sure!"
The price is CA $821
CA $1,167 total
includes taxes & fees
Jun 25 - Jun 26
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, 111 reviews
"We were looking for a nice relaxing weekend getaway from NYC and happened to find this listing. The check in process was easy, and the owners were lovely! We'd absolutely book again."
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, 51 reviews
"Wonderful host. Easy communication. Great house."
gorgeous victorian direct ocean front single family six bedroom, ten rooms
Amazing Lakefront Property
10.0 out of 10, Exceptional, 15 reviews
"This was my second go round staying at this property. My family and I enjoyed it the first time. More so the second time with the upgrades. Being familiar with the area was a great help. This time we went in the lake and enjoyed ourselves. We are looking forward to returning back again. Thank you Raymond for letting us stay at your property. Richard and Joanne"
Amazing Lakefront Property
Direct Waterfront Private Beach Escape
9.8 out of 10, Exceptional, 8 reviews
"We had a beautiful time . Kids didn’t wanted to leave. Amazing views from house , mostly just hung out by the water, watched the birds, and enjoyed the amazing views of the sky. We will be definitely back."
Direct Waterfront Private Beach Escape
Cozy Modern Home
9.6 out of 10, Exceptional, 26 reviews
"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
McAngel Haven: 5 mins from Yale
9.0 out of 10, Wonderful, 2 reviews
"The location was good for our needs and the place well maintained. There were scent devices in many outlets and two of our guests are allergic. We had to unplug them and air out the home. It would be good to alert guests to those devices and allow them to choose to have them not present."
The price is CA $300
CA $725 total
includes taxes & fees
Jun 9 - Jun 10
McAngel Haven: 5 mins from Yale
Trout Brook Trail 2 · Sprawling Classic New England Home
10.0 out of 10, Exceptional, 11 reviews
"The location was amazing! Although on a busy street, it was quiet and still a perfect walking distance from everything. Plenty of bars and restaurants just a few blocks away. The host was super easy to reach and the home was clean and well stocked with essentials."
The price is CA $407
CA $696 total
includes taxes & fees
Jun 12 - Jun 13
Trout Brook Trail 2 · Sprawling Classic New England Home
Near Yale 8 beds Gaming Room
Near Yale 8 beds Gaming Room
lakefront estate
3.8 out of 10, 8 reviews
"Overall do not stay in this house! They are scamming people! They say they are military family yet took advantage of one!! Still owe me my refund and refuse to answer VRBO to give the okay to refund my money! This place was not clean it was very unsanitary and there were drug paraphernalia in the backyard! Towels wet and dirty on the bathroom floor and one of the bedrooms the sheets were dirty in the floor claimed that the house keeper cleaned it! The pool was disgusting!! I have videos pictures...
lakefront estate
Life is Better at the Beach!
10.0 out of 10, Exceptional, 23 reviews
"Nice weekend with friends and young kids. The place is family friendly, clean and has a great atmosphere. Audrey and her husband were very communicative and welcoming! We loved our stay"
Life is Better at the Beach!
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
10.0 out of 10, Exceptional, 103 reviews
"Our family was super comfortable in a charming and beautiful property on the beach. It has gorgeous plantings in the yard and plenty of spacious bedrooms, public areas and a well-appointed kitchen. All thumbs up!"
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Ennis Cottage - A holiday by the sea!
9.8 out of 10, Exceptional, 14 reviews
"Branford is home to our family and this spot was a perfect place to drop the bags! Quient place, clean with all you need for 2 people"
Ennis Cottage - A holiday by the sea!
Beachside Retreat
9.4 out of 10, Exceptional, 3 reviews
"Old world charm meets modern amenities, beach views are calming and relaxing. Exceptional communication with host."
Beachside Retreat
🏡🐕Large Hist. New England home❤🐕Pet❤Reunions😎Beach pass
9.2 out of 10, Wonderful, 82 reviews
"The house was just right for our weekend in the area to attend my son's college graduation. The short walk to wonderful restaurants and the town green in Guilford was a big plus."
The price is CA $344
CA $620 total
includes taxes & fees
Jun 25 - Jun 26
🏡🐕Large Hist. New England home❤🐕Pet❤Reunions😎Beach pass
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See all available properties in Cheshire
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 Cheshire

New Haven Village Suites
3.0 star property
7.6 out of 10, Good, 1,841 reviews
"Comfortable beds and clean for the most part. Rooms are good size. More like a studio apartment. Will stay again sometime 👍 👍 ✌️. "
The price is CA $136
CA $156 total
includes taxes & fees
Jul 1 - Jul 2
New Haven Village Suites
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, 111 reviews
"We were looking for a nice relaxing weekend getaway from NYC and happened to find this listing. The check in process was easy, and the owners were lovely! We'd absolutely book again."
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Luxury Furnished Apartments by Hyatus Downtown at Yale
3.5 star property
9.8 out of 10, Exceptional, 20 reviews
"Everything was okay, the apartment was great, enough space for 3 people. During the nighttime no noise, silence, good for well sleeping and so on… 5 points!"
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.

Cheshire Vacation Homes information

Number of reviews
545
Accommodation
273 Vacation Homes
Lowest Price
CA $300
Highest Price
CA $821

Recent Reviews in Cheshire
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