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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, (10)
"This was a great weekend rental for a trip to a family reunion. The house is very clean and had everything we needed. The location is convenient; it is on a main street but not difficult to get into and out of. Our staybwas very comfortable. "
Stylish & Luxurious 3 BDR Home with Play Station

Lakefront Cottage - Hot Tub, Game Room & Scenic Views

10.0 out of 10, Exceptional, (3)
"Everything was great. "
Lakefront Cottage - Hot Tub, Game Room & Scenic Views

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
28 Apr - 29 Apr
Luxe Lake House in Connecticut

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (11)
"The house was cozy. Check in was easy. The washer dryer was helpful and there were plenty of towels and blankets. All 3 mattresses were quite uncomfortable, and the couches could use an upgrade. There was only one frying pan in the kitchen, which made cooking a little tricky. The windows may not have been opened for a while as it was quite dusty when I opened them to let in some fresh air. "
The price is AED 808
AED 1,149 total
includes taxes & fees
28 Apr - 29 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, (11)
"The house was as advertised and located in a really quiet neighborhood. The host was easy to work with and responded to me each time I texted her. If the opportunity ever comes up again, we would definitely stay at this property again."
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, (5)
"House was extremely clean, plenty of room, and provided all the comforts of home. Owner provided snacks, water, sodas, etc. Everything was perfect. Wouldn't change a thing! "
The price is AED 459
AED 813 total
includes taxes & fees
30 Apr - 1 May
Family Stays: Middletown, CT

Beautiful 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (70)
"We loved our stay at this beautiful cottage. The entire experience was very smooth, from pre-check in to getting there and even offers to help with anything we needed in our stayThe cottage is very cozy and well-cared for. The rooms are comfortable and the Internet fast. There is a lot to do in the area, with New Haven nearby and many good restaurants."
Beautiful 4BR Beach House with Private Beach Access.

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

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

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

10.0 out of 10, Exceptional, (12)
"I've stayed here multiple times and it was amazing as always. Great communication, clean, and beautiful! "
The price is AED 2,204
AED 3,133 total
includes taxes & fees
28 Apr - 29 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, (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

The price is AED 1,969
AED 4,205 total
includes taxes & fees
28 Apr - 29 Apr
Near Yale with Game Room

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

10.0 out of 10, Exceptional, (12)
"Hosts were very communicative and the house had everything I needed. Great location with access to town. "
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!

Enjoy a taste of New England in Historic Guilford Ct

10.0 out of 10, Exceptional, (10)
"Fantastic to host our guests in a pre-1776 house. That alone was a great experience. Add right in the Guilford Green, a great host in Tracy, comfortable beds and lots of touches. We highly recommend and it will be our go-to for our house guests that can’t fit in our house. "
Enjoy a taste of New England in Historic Guilford Ct
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, (2025)
"Good stay. "
New Haven Village Suites

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

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.6 out of 10, Exceptional, (43)
"Love their kitchen. Room is clean and comfortable. The staff is helpful. Will turn. "
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.