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Compare 273 Vacation Homes in Cheshire with updated reviews, rates, and availability.

Room in Apartment - Plaid Room 3min From Yale Univ

3.0 star property
10.0 out of 10, Exceptional, (1)
"The owner is great and made great accommodations for our stay, the price was wonderful. The neighborhood maybe wasent the nicest but thats kinda out of his control."
Room in Apartment - Plaid Room 3min From Yale Univ

Family Gem on Dyer Street

10.0 out of 10, Exceptional, (2)
"Needed a place to stay for the night and it was just the perfect spot. The house was just as it seemed online and it was a lot bigger than I expected. Everything was really nice and the host was super nice and very easy to communicate with. Would 100% recommend to others for their next stay."
The price is AED 694
AED 1,407 total
includes taxes & fees
22 Jan - 23 January 2025
Family Gem on Dyer Street

A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

10.0 out of 10, Exceptional, (24)
"The house is an architectural gem with plenty of space for the family. We enjoyed the fireplace in the evenings."
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

Bright Milford Beach House w/ Outdoor Shower

9.4 out of 10, Exceptional, (6)
"Cute place right across from the beach. Had everything that you need to cook, even a vegetable garden with fresh tomatoes. Comfortable and clean. The beach access is across the street,. "
Bright Milford Beach House w/ Outdoor Shower

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

Enjoy a taste of New England in Historic Guilford Ct

10.0 out of 10, Exceptional, (9)
"Wonderful property combining original details with modern amenities. Well located near the town green and shops. We would definitely stay here again."
Enjoy a taste of New England in Historic Guilford Ct

Ranch style living at its best with country garden & patio!

9.6 out of 10, Exceptional, (8)
"Host worked with me due to larger dog. Very accurate instructions and all amenities were very good. Will stay here again"
Ranch style living at its best with country garden & patio!

The Santiago in Science Park at Yale New Haven

9.6 out of 10, Exceptional, (4)
"The property had everything needed and was a short distance to so many campus sites. Would definitely stay again."
The price is AED 349
AED 628 total
includes taxes & fees
6 Jan - 7 January 2025
The Santiago in Science Park at Yale New Haven

Near Yale 8 beds Gaming Room

The price is AED 1,969
AED 3,968 total
includes taxes & fees
2 Jan - 3 January 2025
Near Yale 8 beds Gaming Room

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

Walk to Beaches: Sunny East Haven Home w/ Grill

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. "
Walk to Beaches: Sunny East Haven Home w/ Grill

Beautiful 3BR, Rare Find, Clean & Guest Favorite

2.0 star property
10.0 out of 10, Exceptional, (2)
"Enjoyed one night in this 3Br property. It was comfortable, secure and easy to locate. Great parking, kitchen, tv and wash/dry facilities. Would recommend."
The price is AED 481
AED 1,093 total
includes taxes & fees
20 Jan - 21 January 2025
Beautiful 3BR, Rare Find, Clean & Guest Favorite

Spacious, quiet suburban getaway in Madison. 15 min from beach & hiking trails!

2.0 star property
10.0 out of 10, Exceptional, (6)
"We had an absolute fantastic time staying at this place. My son was got married at the Beech Tree Cottages (also was the perfect wedding venue) in Madison, Ct. about 15 minutes from the house which worked out perfectly for staying here. From start to finish, everything exceeded our expectations. The communication with Chase was smooth and prompt, making the booking process hassle free. Upon our arrival we were greeted with a welcome gift. The space was clean, modern and beautifully...
Spacious, quiet suburban getaway in Madison. 15 min from beach & hiking trails!

Cozy Coastal Getaway

2.0 star property
10.0 out of 10, Exceptional, (1)
"My daughter and I recently spent four wonderful nights at this incredible home, and we couldn't have been happier. It was cozy, impeccably clean, and the hosts were very responsive. The location was perfect—just halfway to the water and two blocks from the charming Guilford Green. It’s a beautiful area, perfect for walking or running. The hosts went above and beyond by providing thoughtful touches like B&BW toiletries, high-quality linens, coffee, and essential cooking ingredients. We truly...
Cozy Coastal Getaway

Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

10.0 out of 10, Exceptional, (58)
"Great"
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

Cozy newly remodeled home close to major amenities in Connecticut a

8.4 out of 10, Very Good, (17)
"I love staying here. Each visit I bring something new from Louisiana and leave it for the next guest. The cooking supplies are admirable for a home, and especially so for a home away-from-home. We couldn't find a better place to stay. The beds are super comfy, though the furniture requires extra padding. Fortunately there are lots of blankets to use as cishioning."
Cozy newly remodeled home close to major amenities in Connecticut a

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (115)
"Spectacular views from the second floor balcony! very clean and spacious! Highly recommend staying here. "
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Direct Waterfront Private Beach Escape

9.8 out of 10, Exceptional, (12)
"The house was great! Beautiful ocean front property with beachy vibes all throughout the neighborhood and interior of the home. The host was extremely clear on directions and provided amazing instructions. Very comfortable stay! "
Direct Waterfront Private Beach Escape

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

10.0 out of 10, Exceptional, (8)
"This home is just stunning! I used it for a brand photo shoot and I will be back. "
The price is AED 2,204
AED 3,126 total
includes taxes & fees
29 Dec - 30 Dec
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

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
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

3.0 star property
7.6 out of 10, Good, (1984)
"One of our favorites"
The price is AED 360
AED 414 total
includes taxes & fees
26 Dec - 27 Dec
New Haven Village Suites

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

10.0 out of 10, Exceptional, (127)
"Although I went went it is cold the view and location were excellant. I can definately see taking advantage of this place during the summer. The host was responsive and available. "
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, (37)
"I was completely satisfied with my stay. Apartment had wonderful amenities and an amazing view. Great location near downtown restaurants too."
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.