Search Vacation Homes in Cheshire Historic District

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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

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

Stylish & Luxurious 3 BDR Home with Play Station
Fridge, microwave, oven, stovetop

Stylish & Luxurious 3 BDR Home with Play Station

9.4 out of 10, Exceptional, (10)
"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 Retreat w Hot Tub, Game Room & Peaceful Views - Fall Mountain Lake
Outdoor spa tub

Lakefront Retreat w Hot Tub, Game Room & Peaceful Views - Fall Mountain Lake

10.0 out of 10, Exceptional, (3)
"Everything was great. "
Lakefront Retreat w Hot Tub, Game Room & Peaceful Views - Fall Mountain Lake
Luxe Lake House in Connecticut
Fridge, microwave, oven, stovetop

Luxe Lake House in Connecticut

10.0 out of 10, Exceptional, (2)
"Couldn’t have asked for a better weekend! Thank you so much Shawn! "
The price is AED 1,288
AED 3,322 total
includes taxes & fees
6 May - 7 May
Luxe Lake House in Connecticut
Tranquil Litchfield Connecticut Retreat".
Property grounds

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (11)
"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 1,160 total
includes taxes & fees
5 May - 6 May
Tranquil Litchfield Connecticut Retreat".
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Outdoor pool

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
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (11)
"This pet friendly home is located in a great residential neighborhood close to Yale campus and the bowl. Very clean and comfortable. Great fenced yard for pets and kids."
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
Interior

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
Fridge, microwave, oven, stovetop

Family Stays: Middletown, CT

10.0 out of 10, Exceptional, (6)
"Our experience with this facility, from online service to exiting the residence, was the most pleasurable experience, for staying in accommodations when traveling!!The owner was a complete gentleman and it was absolutely wonderful experience to meet and talk with him."
Family Stays: Middletown, CT
Beautiful 4BR Beach House with Private Beach Access.
Beach nearby, beach towels

Beautiful 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (70)
"My husband and I stayed in this lovely home for a long weekend while attending the Soundside music festival. It was perfect for what we were looking for; comfortable beds, equipped kitchen and nice location. We had the entire private beach to ourselves. The owners were also quick to respond to all questions. "
Beautiful 4BR Beach House with Private Beach Access.
Direct Waterfront Private Beach Escape
Outdoor dining

Direct Waterfront Private Beach Escape

9.8 out of 10, Exceptional, (13)
"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
Property grounds

Cozy dog friendly updated house in quiet village adjacent to park

10.0 out of 10, Exceptional, (26)
"Stayed for two weeks and really enjoyed the experience. Anthony is a fantastic host with great communication. "
Cozy dog friendly updated house in quiet village adjacent to park
Charming West Haven Home - Walk to Beach!
Fridge, microwave, stovetop, dishwasher

Charming West Haven Home - Walk to Beach!

8.6 out of 10, Excellent, (11)
"Throughly enjoyed our stay! Was a wonderful experience. The house and area were wonderful!"
Charming West Haven Home - Walk to Beach!
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Smart TV, fireplace, video games

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

10.0 out of 10, Exceptional, (13)
"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
5 May - 6 May
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
Fridge, microwave, oven, stovetop

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
Beach nearby

Walk to Beaches: Sunny East Haven Home w/ Grill

2.0 star property
10.0 out of 10, Exceptional, (4)
"The beds were so comfy. The shower was awesome. Everything was perfect"
Walk to Beaches: Sunny East Haven Home w/ Grill
Near Yale with Game Room
Fridge, microwave, oven, stovetop

Near Yale with Game Room

The price is AED 1,969
AED 4,183 total
includes taxes & fees
5 May - 6 May
Near Yale with Game Room
Charming home, easy access - everything Branford. Super Host with 5-Star Rating
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (12)
"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
Cozy 2 bedroom home located minutes from downtown
Interior

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!
Outdoor dining

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!
Exterior

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

9.6 out of 10, Exceptional, (8)
"Solid location and quiet neighborhood good after a long day."
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
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (2026)
"Okay place to stay "
New Haven Village Suites
Luxury Furnished Apartments by Hyatus Downtown at Yale
Honeymoon Apartment, 3 Bedrooms, Kitchen | In-room dining

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.6 out of 10, Exceptional, (45)
"Love their kitchen. Room is clean and comfortable. The staff is helpful. Will turn. "
Luxury Furnished Apartments by Hyatus Downtown at Yale
Luxury Apartments by Hyatus at Pierpont
Seasonal outdoor pool

Luxury Apartments by Hyatus at Pierpont

4.0 star property
9.6 out of 10, Exceptional, (15)
"My husband and I both loved this property and it’s convenient location; so much that we even discussed purchasing one of the apartments as a condo! We ran a bit over checkout and the property manager was very communicative and accommodating. A wonderfully quaint, quiet, and walkable location with great food options in close proximity to prominent institutions. Definitely will stay again. "
Luxury Apartments by Hyatus at Pierpont
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.