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Check prices for these dates

Next weekend
2 Jum. I - 4 Jum. I
In two weeks
9 Jum. I - 11 Jum. I
In one month
23 Jum. I - 25 Jum. I
In two months
20 Jum. II - 22 Jum. II

Compare 335 Vacation Homes in Cheshire with updated reviews, rates, and availability.

Lakeside luxury: beautiful, relaxing 4 bedroom home
Property grounds

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (20)
"This property was perfect for our weekend trip to celebrate my nieces family/birthday weekend at Fairfield"
Lakeside luxury: beautiful, relaxing 4 bedroom home
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
New Madison beach house - Ocean front- Great views- booking Summer 2025
Fridge, microwave, oven, stovetop

New Madison beach house - Ocean front- Great views- booking Summer 2025

10.0 out of 10, Exceptional, (57)
"Great location "
New Madison beach house - Ocean front- Great views- booking Summer 2025
Lakefront Cottage - Hot Tub, Game Room & Scenic Views
Outdoor spa tub

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
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 SAR 1,343
SAR 3,428 total
includes taxes & fees
29 Apr - 30 Apr
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 SAR 825
SAR 1,177 total
includes taxes & fees
27 Apr - 28 Apr
Tranquil Litchfield Connecticut Retreat".
Grammy's Lake House w/ Private Waterfront Access
TV

Grammy's Lake House w/ Private Waterfront Access

9.4 out of 10, Exceptional, (12)
"Enjoyable stay, nice property and great views. The home is aged, but the location is amazing! We had a nice weekend excursion to enjoy New England in October. "
Grammy's Lake House w/ Private Waterfront Access
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
Fridge, microwave, oven, stovetop

Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

10.0 out of 10, Exceptional, (42)
"This property is beautiful and the house is spacious and well equipped for a wonderful stay. The host was attentive and easy to contact when it was necessary. Such a fantastic choice for a stay in a delightful town. "
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
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
Fridge, microwave, oven, stovetop

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (19)
"Clean, Cozy and Comfortable "
Charming 3BR Hilltop House, Newly Remodeled with Arcade
WeHa Oak Haven
Private kitchen

WeHa Oak Haven

10.0 out of 10, Exceptional, (5)
"Lovely property in a great area of West Hartford. Will definitely stay again!"
WeHa Oak Haven
Family Stays: Middletown, CT
Fridge, microwave, oven, stovetop

Family Stays: Middletown, CT

10.0 out of 10, Exceptional, (5)
"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."
The price is SAR 469
SAR 830 total
includes taxes & fees
29 Apr - 30 Apr
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.
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Exterior

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (116)
"Had a quick work trip and wish we stayed longer! "
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Ocean Front Beach House with Private Beach Access - Newly Renovated!
Smart TV

Ocean Front Beach House with Private Beach Access - Newly Renovated!

10.0 out of 10, Exceptional, (16)
"Wonderful week at this beautiful home! Great space, comfortable furniture, well equipped. Breathtaking sunrises AND sunsets. Highly recommend this home !"
Ocean Front Beach House with Private Beach Access - Newly Renovated!
Direct Waterfront Private Beach Escape
Fridge, microwave, oven, stovetop

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
Litchfield County Four Season Country Paradise
Outdoor pool, a heated pool

Litchfield County Four Season Country Paradise

9.6 out of 10, Exceptional, (40)
"Overall rating 5/5. I would recommend this home to other families and would stay again. "
Litchfield County Four Season Country Paradise
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, (12)
"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 SAR 2,251
SAR 3,200 total
includes taxes & fees
27 Apr - 28 Apr
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
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

Quiet 2bd Townhome apt in the heart of Cheshire.
Fridge, microwave, oven, stovetop

Quiet 2bd Townhome apt in the heart of Cheshire.

10.0 out of 10, Exceptional, (1)
"Overall a positive experience. Property was clean and worked out really well for us as location was close to family we were visiting. We are from Florida, and it was cold in CT and the heat worked great so that was really good. Andrew was responsive to requests. Only criticism was in some of the set up. There are no dressers, so you need to stack your clothes on shelves in closet, which was not terrible. Also, the only mirror in the entire place was in the bathroom downstairs (bedrooms...
The price is SAR 409
SAR 718 total
includes taxes & fees
7 May - 8 May
Quiet 2bd Townhome apt in the heart of Cheshire.
New Haven Village Suites
Suite, Multiple Beds | Egyptian cotton sheets, premium bedding, pillowtop beds, desk

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (2025)
"Okay place to stay "
New Haven Village Suites
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Outdoor pool, a heated pool

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
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.