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Compare 232 Vacation Homes in Cheshire Historic District with updated reviews, rates, and availability.

Stylish & Luxurious 3 BDR Home with Play Station

9.4 out of 10, Exceptional, (9)
"We needed a place for our family of 6 to stay while visiting family in the area. This place was exactly what we needed, as advertised, and the owner was quick with communications. We would definitely stay here again!"
Stylish & Luxurious 3 BDR Home with Play Station

Lakefront Getaway w Hot Tub, Game Room & Views - Pet-Friendly

10.0 out of 10, Exceptional, (1)
"Beautiful view from the upstairs window. I enjoyed the pellet stove on the cold days."
The price is AED 661
AED 1,308 total
includes taxes & fees
1 Apr - 2 Apr
Lakefront Getaway w Hot Tub, Game Room & Views - Pet-Friendly

Luxe Lake House in Connecticut

10.0 out of 10, Exceptional, (2)
"The house easily accommodated my friends and family for a weekend of relaxation. The place is very spacious with all modern amenities. We especially loved waking up to the gorgeous view of the lake in the back. The views were breathtaking. Would definitely consider going back. "
The price is AED 1,288
AED 3,322 total
includes taxes & fees
2 Apr - 3 Apr
Luxe Lake House in Connecticut

Tranquil Litchfield Connecticut Retreat".

9.4 out of 10, Exceptional, (9)
"This is a neat, clean and lovely little place that perfectly suited our needs. It had all the amenities we needed for our short stay. Jose was a gracious host, answering all of my questions promptly - even the one about the mattresses which were incredibly comfortable! "
The price is AED 808
AED 1,149 total
includes taxes & fees
1 Apr - 2 Apr
Tranquil Litchfield Connecticut Retreat".

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

10.0 out of 10, Exceptional, (7)
"It was a great house to host our family for Thanksgiving dinner! "
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

10.0 out of 10, Exceptional, (9)
"The house was exactly what I needed to be close to my son at Yale for a few days. The house and neighborhood was great for our dog. The host had just about everything we needed for a comfortable stay, and the welcome snacks and extra toilet paper, etc. was welcomed. The only thing I would say is the shower in the bathroom was very small…think RV shower, and there didn’t appear to be a shower head, so the water came out really hard like a water hose. But other than that, nice little house in a...
7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (19)
"Very nice clean house. Felt like coming home after work"
Charming 3BR Hilltop House, Newly Remodeled with Arcade

Family Stays: Middletown, CT

10.0 out of 10, Exceptional, (4)
"We came to the area for a long weekend event at Wesleyan University. I had never booked through VRBO and was not familiar with the process. From my first communication with Gilbert I felt like I was going to visit family. He was amazing to communicate with provided information about the area and the process and was super accommodating when he learned our flight was arriving early. From the moment we stepped through the door we knew our stay would be special. The home is beautiful, beds...
The price is AED 514
AED 891 total
includes taxes & fees
28 Apr - 29 Apr
Family Stays: Middletown, CT

Beautiful 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (69)
"our annual girls (5) trip took us to Branford, CT this year. It was awesome to have a private beach access even though we couldn’t get in the water, but it was great for strolls and shell collecting. Would definitely do better with a second bathroom, but we managed just fine. Overall, it’s a nice little place to stay for a getaway. My only issue is not with the hosts or place, but with one of the fees and the checkout process. However, it does not take away from our stay. "
Beautiful 4BR Beach House with Private Beach Access.

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

Cozy dog friendly updated house in quiet village adjacent to park

10.0 out of 10, Exceptional, (26)
"My family and I had a wonderful week long stay at this beautiful cozy home. Plenty of amenities in the house to make everyone happy. The convenience of 3 bathroom with a large family was wonderful. The location was great for everything i meeded. The park next door is a great addition to get the kids outside. Thankbyou so much for the great communication and hospitality "
Cozy dog friendly updated house in quiet village adjacent to park

Charming West Haven Home - Walk to Beach!

8.6 out of 10, Excellent, (11)
"Clean house in a convenient and quiet location. Close to many store and restaurants. House was well equipped. Sauna was a nice extra. Only complaints are that the bed in the third bedroom is not for adults and the towels need to be replaced. We would definitely rent the house again when in the area. "
Charming West Haven Home - Walk to Beach!

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

10.0 out of 10, Exceptional, (9)
"This home is one of the most beautiful homes! I love all of the natural light and the clean aesthetic. Such a high-end home! Chad is great with communication and makes the whole experience seamless! I highly recommend it! "
The price is AED 2,204
AED 3,115 total
includes taxes & fees
1 Apr - 2 Apr
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants

10.0 out of 10, Exceptional, (39)
"Excellent stay in s as wonderful house. "
Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants

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

Near Yale with Game Room

The price is AED 1,969
AED 4,180 total
includes taxes & fees
1 Apr - 2 Apr
Near Yale with Game Room

Charming home, easy access - everything Branford. Super Host with 5-Star Rating

10.0 out of 10, Exceptional, (10)
"Property was exactly as decribed. Comfortable, roomy, good well equipped kitchen and warm for the cooler time of the year. Recommended "
Charming home, easy access - everything Branford. Super Host with 5-Star Rating

Cozy 2 bedroom home located minutes from downtown

9.6 out of 10, Exceptional, (24)
"We were in town for our daughter’s white coat ceremony at Quinnipiac. We were located in a good area with easy access to the campus and restaurants. The house was clean and met our needs. Our host was responsive to all our questions. "
Cozy 2 bedroom home located minutes from downtown

Elegant Middlefield Getaway w/ Game Room!

9.8 out of 10, Exceptional, (12)
"Very comfortable modern house"
Elegant Middlefield Getaway w/ Game Room!

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!
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 Historic District

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (2019)
"Okay place to stay "
The price is AED 334
AED 384 total
includes taxes & fees
7 Apr - 8 Apr
New Haven Village Suites

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.6 out of 10, Exceptional, (39)
"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

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

10.0 out of 10, Exceptional, (128)
"having previously rented VRBO properties in Palm Springs, West Palm Beach & Ft. Lauderdale I can confirm this property is exceptional. The studio has 1st tier amenities, waterfront location & in addition the hosts provided most welcoming foods and snacks, an overall wonderful experienceJimBrooklyn, NY"
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
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.