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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 194 Vacation Homes in Cheshire Historic District with updated reviews, rates, and availability.

McAngel Haven: 5 mins from Yale
Spaciously Stylish Living Area with Fireplace and Dining View

McAngel Haven: 5 mins from Yale

9.8 out of 10, Exceptional, (10)
"Excellent to had a nice house like that "
The price is AED 937
AED 2,104 total
includes taxes & fees
24 Feb - 25 Feb
McAngel Haven: 5 mins from Yale
Amazing Lakefront Property
Dining

Amazing Lakefront Property

9.8 out of 10, Exceptional, (24)
"Absolutely beautiful house! Super clean! Superb setting! Very comfortable! Amazing view! Many amenities! Host very responsive and kind! The property manager quickly responded to our needs. My family and friends loved the spectacular experience and would definitely comeback! "
Amazing Lakefront Property
NEW-Another Fun Downtown Location 1st floor
Exterior

NEW-Another Fun Downtown Location 1st floor

2.0 star property
10.0 out of 10, Exceptional, (9)
"It was a nice quiet valuable time spent together .just what we needed for that very special memorable time. Thanks."
NEW-Another Fun Downtown Location 1st floor
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Exterior

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

10.0 out of 10, Exceptional, (9)
"My friends and I have stayed twice now at this house and have had the best time both times! It has everything we could need in the house and we can’t wait to be back again!"
The price is AED 2,204
AED 3,133 total
includes taxes & fees
23 Feb - 24 Feb
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Near Yale with Game Room
Exterior

Near Yale with Game Room

The price is AED 1,969
AED 4,180 total
includes taxes & fees
23 Feb - 24 Feb
Near Yale with Game Room
Family Stays: Middletown, CT
Living room

Family Stays: Middletown, CT

10.0 out of 10, Exceptional, (2)
"We came to stay at Gilbert’s for a quick ski weekend at Powder Ridge. Gilbert was incredibly gracious and accommodating. He was very easy to communicate with, and really went out of his way to make us feel at home. The location is a little loud at night/early morning, as it is very close to a main road. But the property itself was exactly as described. Clean, comfortable, and very welcoming. "
The price is AED 342
AED 656 total
includes taxes & fees
22 Feb - 23 Feb
Family Stays: Middletown, CT
Beautiful 3BR, Rare Find, Clean & Guest Favorite
Living area

Beautiful 3BR, Rare Find, Clean & Guest Favorite

2.0 star property
10.0 out of 10, Exceptional, (2)
"Nice clean 3 bedroom that was as described. It was a short drive to downtown West Hartford."
The price is AED 481
AED 1,090 total
includes taxes & fees
3 Mar - 4 Mar
Beautiful 3BR, Rare Find, Clean & Guest Favorite
Enjoy a taste of New England in Historic Guilford Ct
Property grounds

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!
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!
Walk to Beaches: Sunny East Haven Home w/ Grill
East Haven Vacation Rental | 4BR | 1.5BA | 1,520 Sq Ft | Stairs Required

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
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
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
Spacious 18th Century Victorian Mansion - Sleep 16+ Large Group
Exterior detail

Spacious 18th Century Victorian Mansion - Sleep 16+ Large Group

10.0 out of 10, Exceptional, (1)
"We had a lovely family gathering with 14 adults and a toddler - the house was perfect for a large family meal and had room for everyone. Lots of games, a pool table, and electric fireplace were great additions. Rick was very helpful and easy to communicate with. Convenient on site parking. As stated in listing, the bedrooms are on 2nd and 3rd floor, with grand/tall staircases. Overall it was a great place for our family to celebrate together!"
The price is AED 3,526
AED 6,220 total
includes taxes & fees
22 Feb - 23 Feb
Spacious 18th Century Victorian Mansion - Sleep 16+ Large Group
Charming Coastal Retreat Steps from the Beach!
Living area

Charming Coastal Retreat Steps from the Beach!

9.8 out of 10, Exceptional, (31)
"The house was perfect for our multi generation gathering, spacious enough for all. The kitchen was well equipped for our cooking needs. The beds very comfortable. Would highly recommend it!"
Charming Coastal Retreat Steps from the Beach!
Hidden Gem: Newly Remodeled 5-Bedroom Haven with Central AC in New Haven
Exterior

Hidden Gem: Newly Remodeled 5-Bedroom Haven with Central AC in New Haven

Hidden Gem: Newly Remodeled 5-Bedroom Haven with Central AC in New Haven
Cozy dog friendly updated house in quiet village adjacent to park
Exterior

Cozy dog friendly updated house in quiet village adjacent to park

10.0 out of 10, Exceptional, (25)
"The house is pretty nice and there's space for friends to chill and relax"
Cozy dog friendly updated house in quiet village adjacent to park
11 Mi to Powder Ridge Mountain: Connecticut Home
Killingworth Vacation Rental | 4BR | 2BA | 2,034 Sq Ft | Stairs Required

11 Mi to Powder Ridge Mountain: Connecticut Home

9.6 out of 10, Exceptional, (4)
"Everything about our stay was flawless. The instructions prior to arrival were complete and clear. The property was clean and stocked with basic necessities. The pool was an added plus.Excellent communication from our gracious hostess."
11 Mi to Powder Ridge Mountain: Connecticut Home
Cozy Lakefront Bungalow w firepit/dock/kayaks
Covered Mahogany deck, perfect for drinks and hanging out

Cozy Lakefront Bungalow w firepit/dock/kayaks

10.0 out of 10, Exceptional, (25)
"This is our second time visiting the area and staying at this beautiful home. It's close to many activities for children and adults, easy to access food and services and a beautiful overall area and home. We truly enjoy visiting!"
Cozy Lakefront Bungalow w firepit/dock/kayaks
The Connecticut Chalet - On 5 Acres!
Interior

The Connecticut Chalet - On 5 Acres!

10.0 out of 10, Exceptional, (2)
"If you’re looking for a relaxing, unique/fun home this is it!! The host was amazing & left no questions to ask. The home is fully stocked with all your needs from cooking utensils, wood to start a warm fire & even games for in between time. The bedrooms are cozy and the beds are super soft. The deck & sun room/dining room was a fav, the views are amazing. I would certainly recommend and even stay here again. Thank you "
The Connecticut Chalet - On 5 Acres!
Charming home, easy access - everything Branford. Super Host with 5-Star Rating
Exterior

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

10.0 out of 10, Exceptional, (10)
"Cottage has two lovely bedrooms with full bath, very clean and well-equipped kitchen, nice dining and living rooms all on first floor."
Charming home, easy access - everything Branford. Super Host with 5-Star Rating
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
Front of property

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (2005)
"Easy fast check in"
The price is AED 324
AED 373 total
includes taxes & fees
4 Mar - 5 Mar
New Haven Village Suites
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, (38)
"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
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms
Sunset 🌅 Living room view .

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

10.0 out of 10, Exceptional, (59)
"Our family ranged in ages from 13 to 96. We were 12 people for a couple days and then 10. We all had a marvelous time and my mom just can’t stop talking about how beautiful the view and the antique furniture was. It was difficult for that many people only having two bathrooms, but we made it work. We did run out of hot water so we learned to scatter showers when possible. The view is amazing and the location was wonderful for us. I can’t say enough, how accommodating our hostess was. We told her...
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms
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.