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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Vacation Homes in Cheshire

Fridge, microwave, oven, stovetop
Historic New England home ,Reunions Beach pass

Historic New England home ,Reunions Beach pass

Guilford
9.2 out of 10, Wonderful, (90)
"The location of this place is best!"
United States
Dr. Maureen C.
The price is SAR 642
SAR 1,539 total
includes taxes & fees
3 Dec - 4 Dec
Historic New England home ,Reunions Beach pass
Smart TV, fireplace, video games
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

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

Durham
10.0 out of 10, Exceptional, (24)
"As advertised. Enjoyed our stay. "
United States
Jeff C.
The price is SAR 2,196
SAR 3,566 total
includes taxes & fees
3 Dec - 4 Dec
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Interior
Cozy Guest Suite in Historic Home

Cozy Guest Suite in Historic Home

Middletown
10.0 out of 10, Exceptional, (1)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is SAR 554
SAR 806 total
includes taxes & fees
15 Dec - 16 Dec
Cozy Guest Suite in Historic Home
Interior
2-bedroom Oasis in Portland

2-bedroom Oasis in Portland

2.0 star property
Portland
The price is SAR 435
SAR 2,009 total
includes taxes & fees
3 Dec - 4 Dec
2-bedroom Oasis in Portland
Property grounds
One private bedroom with work space and shared home with spa.

One private bedroom with work space and shared home with spa.

Rocky Hill
The price is SAR 345
SAR 515 total
includes taxes & fees
3 Dec - 4 Dec
One private bedroom with work space and shared home with spa.
Fridge, microwave, oven, stovetop
Family Stays: Middletown, CT

Family Stays: Middletown, CT

Middletown
10.0 out of 10, Exceptional, (18)
"The house was great, the welcome snacks and balloons were thoughtful and the kitchen coffee, etc, was much appreciated. This was an excellent stay and I highly recommend it!"
United States
Cari M.
The price is SAR 450
SAR 863 total
includes taxes & fees
15 Dec - 16 Dec
Family Stays: Middletown, CT
Dining
#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat

Middletown
9.8 out of 10, Exceptional, (21)
"We had a wonderful stay at this property! The house itself was beautiful—spacious, clean, and incredibly comfortable. The setting was just as impressive, offering peaceful views and a great atmosphere to relax and unwind. Everything was exactly as described, if not better. We would absolutely stay here again and highly recommend it to anyone looking for a serene and well-appointed home base for our stay. "
United States
Nichole N.
The price is SAR 447
SAR 1,099 total
includes taxes & fees
10 Dec - 11 Dec
#24 *Serenity* A Lakefront Cottage Retreat
Microwave, oven, stovetop, dishwasher
Cozy East Haven Home • Near Beach & Yale

Cozy East Haven Home • Near Beach & Yale

Momauguin
10.0 out of 10, Exceptional, (4)
"Such a cute place, loved all the nautical touches. Great space for a weekend getaway, pretty well-stocked kitchen, clean & cozy. Really appreciated the outdoor space & amenities too! And Michael the host is very responsive & helpful! "
United States
Amal A.
The price is SAR 469
SAR 614 total
includes taxes & fees
2 Jan - 3 January 2026
Cozy East Haven Home • Near Beach & Yale
Fridge, microwave, oven, stovetop
Private Apartment in Berlin

Private Apartment in Berlin

2.0 star property
Berlin
9.2 out of 10, Wonderful, (5)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
United States
Stacy B.
The price is SAR 439
SAR 1,186 total
includes taxes & fees
7 Dec - 8 Dec
Private Apartment in Berlin
Fridge, microwave, oven, stovetop
Charming 3-Bedroom Home with Modern Comforts in West Hartford

Charming 3-Bedroom Home with Modern Comforts in West Hartford

2.0 star property
West Hartford
8.6 out of 10, Excellent, (9)
"Great house in a safe neighborhood with a fenced in yard. Amenities provided. "
United States
Ben H.
The price is SAR 516
SAR 1,149 total
includes taxes & fees
3 Dec - 4 Dec
Charming 3-Bedroom Home with Modern Comforts in West Hartford
TV
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

New Britain
10.0 out of 10, Exceptional, (7)
"Beautiful, clean, bright, spacious and easy to travel to. Felt safe. Nice to have the garage to park in. "
United States
Angela L.
The price is SAR 422
SAR 932 total
includes taxes & fees
7 Dec - 8 Dec
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
1 bedroom, iron/ironing board, WiFi, bed sheets
Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment

Wallingford Center
9.0 out of 10, Wonderful, (13)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is SAR 431
SAR 1,089 total
includes taxes & fees
15 Dec - 16 Dec
Once the old Schools house now a newly furnished Apartment
TV
Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private

Wallingford
10.0 out of 10, Exceptional, (9)
"The flat has a nice layout and was very comfortable. We enjoyed our stay."
United States
Mary R.
The price is SAR 431
SAR 1,063 total
includes taxes & fees
2 Jan - 3 January 2026
Newly Remodeled 1-BR Close to Everything yet Very Private
Smart TV
#28- *Modern Bungalow*

#28- *Modern Bungalow*

New Britain
9.0 out of 10, Wonderful, (2)
"This stay was very comfortable and also not too fat from the Convention Center either "
United States
Vicente B.
The price is SAR 507
SAR 988 total
includes taxes & fees
21 Dec - 22 Dec
#28- *Modern Bungalow*
Terrace/patio
The Jewel of The Cove - Historic Coastal Retreat

The Jewel of The Cove - Historic Coastal Retreat

2.0 star property
East Shore
10.0 out of 10, Exceptional, (5)
"loved it so much, beautiful property 100 % would stay again "
United States
Leilani R.
The price is SAR 777
SAR 1,944 total
includes taxes & fees
9 Dec - 10 Dec
The Jewel of The Cove - Historic Coastal Retreat
Outdoor pool
Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

East Shore
8.0 out of 10, Very Good, (1)
"It was a nice place. We were in CT for a wedding. It was very close to the venue. The bathrooms were a good size for 10 people staying there getting ready. I would definitely return for another family event in the area. Thank you to the home owners."
United States
Suzanne S.
The price is SAR 1,291
SAR 2,329 total
includes taxes & fees
2 Jan - 3 January 2026
Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches
Smart TV, books
Clear LI Sound waterview, Wedding pics, Yale&Beach

Clear LI Sound waterview, Wedding pics, Yale&Beach

East Shore
10.0 out of 10, Exceptional, (10)
"My husband and I enjoyed our stay. The host was very easy to communicate with and very responsive. The property is clean and lovely. Gorgeous view. "
United States
Kerri F.
The price is SAR 2,158
SAR 3,665 total
includes taxes & fees
15 Dec - 16 Dec
Clear LI Sound waterview, Wedding pics, Yale&Beach
Fridge, microwave, oven, coffee/tea maker
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Fair Haven
7.6 out of 10, Good, (5)
"Thanks for hosting us! It was clean and nice. For future guests, a long body mirror might be nice but we had a wonderful time and appreciated you bringing us extra towels quickly!"
United States
Jamie S.
The price is SAR 456
SAR 877 total
includes taxes & fees
3 Dec - 4 Dec
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Interior
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Fair Haven
9.6 out of 10, Exceptional, (14)
"Had a really nice stay, enjoyed this open airy space with comfortable beds and beautiful light with a view of the river. Very nice time, would stay again."
United States
Brian B.
The price is SAR 635
SAR 1,192 total
includes taxes & fees
3 Dec - 4 Dec
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Interior
Gorgeous Waterfront 2:1 - 2 houses in 1 building.

Gorgeous Waterfront 2:1 - 2 houses in 1 building.

Fair Haven
Gorgeous Waterfront 2:1 - 2 houses in 1 building.
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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Top Cheshire Hotel Reviews

Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

10/10 Excellent
"We have stayed at this hotel multiple times. It is a very convenient location, it is always kept very clean, and it is a very good value noting also the exceptional complimentary breakfast. This trip stood out in that the customer service provided at the front desk was above and beyond to make our stay even better. Donna at the front desk went out of her way to correct a booking problem with our room and her kindness and friendliness made us feel both welcome and appreciated as guests. She provided exceptional customer service that is uncommon to find nowadays and she did it cheerfully despite the challeges brought about by a holiday weekend."
lea 3-night trip
Posted 1 day ago
Hampton Inn & Suites Hartford/East Hartford