Holiday Homes in Cheshire Historic District

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Featured Holiday Homes in Cheshire Historic District and around

#29 - Modern 5 Bedroom/2 Bath

10.0 out of 10, Exceptional, (2)
"We enjoyed staying at this house while in town for a family wedding. The house was clean and recently renovated. Beds were comfortable and linens and towels were provided. Be aware there are no young child items. We brought our own baby gate for the stairs and plastic cups and dishwater. Plenty of nice cooking tools in the kitchen. Overall we enjoyed our stay."
The price is €573
includes taxes & fees
20 Dec - 21 Dec
#29 - Modern 5 Bedroom/2 Bath

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

Walkable New Haven Retreat w/ Ocean Views!

9.6 out of 10, Exceptional, (21)
"We enjoyed our time at this great property. Everything was clean and the listing is accurate. Don't hesitate to book your stay."
Walkable New Haven Retreat w/ Ocean Views!

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!

9.8 out of 10, Exceptional, (7)
"We had a great time at this home and it is really fabulously decorated. Reggie called us right back when we had a question. "
Ranch style living at its best with country garden & patio!

Near Yale 8 beds Gaming Room

The price is €1,073
includes taxes & fees
1 Dec - 2 Dec
Near Yale 8 beds Gaming Room

NEW! Charming Riverside Home-CT River Private, Spacious, Family & Pet Friendly

10.0 out of 10, Exceptional, (1)
"Great home and nice activities with kids."
The price is €399
includes taxes & fees
1 Dec - 2 Dec
NEW! Charming Riverside Home-CT River Private, Spacious, Family & Pet Friendly

Luxe Lake House in Connecticut

The price is €904
includes taxes & fees
10 Dec - 11 Dec
Luxe Lake House in Connecticut

Beautiful 3BR, Rare Find, Clean & Guest Favorite

2.0 star property
10.0 out of 10, Exceptional, (1)
"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 €360
includes taxes & fees
1 Dec - 2 Dec
Beautiful 3BR, Rare Find, Clean & Guest Favorite

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!

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!

Waterfront 3-bedroom house with AC and WiFi in tranquil Southbury

8.0 out of 10, Very good, (2)
"My husband, daughter and myself stayed at the house for a couple nights. The house was spacious, clean, had comfortable beds and was right on the lake. We loved that! Unfortunately, we arrived in the dark and the roads were a little tricky at night for our first time driving it. I know by the picture that there were some stairs to get to the house. I was thinking maybe 20 but 75? Since my husband has knee issues and I have back issues, it would have been good information to have on the...
Waterfront 3-bedroom house with AC and WiFi in tranquil Southbury

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

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 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

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

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

9.6 out of 10, Exceptional, (11)
"It was great very clean super lovely "
The price is €269
includes taxes & fees
3 Dec - 4 Dec
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Heavenly Home in New Haven

8.8 out of 10, Excellent, (15)
"The property was prepared well and we enjoyed our stay. Thanks"
The price is €603
includes taxes & fees
29 Nov - 30 Nov
Heavenly Home in New Haven

McAngel Haven: 5 mins from Yale

9.6 out of 10, Exceptional, (5)
"This rental was a wonderful house for our family vacation and we couldn't have been happier with our experience. After a long and eventful trip, it was nice being able to relax and recuperate in the wonderful environment this home provided. The house was spacious, clean, and beautifully decorated. We especially enjoyed the many bedrooms and bathrooms that was available making it very easy for our big family to get settled in the home. The property manager was incredibly responsive,...
The price is €516
includes taxes & fees
1 Dec - 2 Dec
McAngel Haven: 5 mins from 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.
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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, (1966)
"Convenient location, helpful staff, comfortable bed. Thanks!"
The price is €108
includes taxes & fees
9 Dec - 10 Dec
New Haven Village Suites

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

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.