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Cheshire Vacation Rentals

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Vacation Rentals in Cheshire

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

9.6 out of 10, Exceptional, (7)
"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 CA $129
CA $238 total
includes taxes & fees
Jul 29 - Jul 30
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (135)
"Perfect location for a get-away! Beautiful location on the water. The cottage was cozy & had everything we needed. Very clean. Lots to do in the area. Host was very nice We had a great time and will absolutely be back! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

10.0 out of 10, Exceptional, (5)
The price is CA $543
CA $990 total
includes taxes & fees
Jul 28 - Jul 29
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

8.8 out of 10, Excellent, (20)
"We had a wonderful time at the cabin by the lake. Beautiful views in the Morning!! Loved it."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Luxury Apartments by Hyatus at Pierpont

4.0 star property
9.4 out of 10, Exceptional, (19)
"Excellent location downtown and close to yale. A lot of complimentary amenities and activities. Very nice size rooms. A nice residential feel for a weeks stay."
Luxury Apartments by Hyatus at Pierpont

Cozy apartment in charming Hartford with AC, WiFi

10.0 out of 10, Exceptional, (1)
The price is CA $156
CA $231 total
includes taxes & fees
Jul 27 - Jul 28
Cozy apartment in charming Hartford with AC, WiFi

Lux Boutique Large Private LOFT Pratt St Hartford

9.0 out of 10, Wonderful, (17)
"I am impressed with the Lux Private Loft. Absolutely Gorgeous!!. I hope to return. The kitchen area, enormous shower, large screen t.v. I will book again as soon as possible."
The price is CA $189
CA $268 total
includes taxes & fees
Aug 2 - Aug 3
Lux Boutique Large Private LOFT Pratt St Hartford

Cozy 3 bedroom minutes from Yale and the beach

8.0 out of 10, Very good, (1)
"Would recommend. It was quaint second story apartment in an older home. Nicely updated."
Cozy 3 bedroom minutes from Yale and the beach

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

10.0 out of 10, Exceptional, (47)
"Home was very comfortable and a great location. The views were spectacular. Owner gave us great recommendations for restaurants and nearby attractions. "
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

Bright Milford Beach House w/ Outdoor Shower

9.4 out of 10, Exceptional, (11)
"We had the best time! It was clean, good location, and the owner was wonderful! We even got to go the beach in December! We would definitely rent this place again!!"
Bright Milford Beach House w/ Outdoor Shower

Cozy 2-bedroom Cottage with Access to Bantam Lake

9.6 out of 10, Exceptional, (17)
"Even with horrible weather, we had a wonderful stay!"
Cozy 2-bedroom Cottage with Access to Bantam Lake

Modern Condo|DWNTN Hartord| XL Center| GYM

4.0 out of 10, (2)
"The location was fantastic.Check-In, Parking and Check-Out easy.The images of the condo were misleading.- cockroaches were present- Floors were not swept- sofa bed sheets were still on bed and unwashed- makeup on the pillow cases from the pullout couch and the hair dryer bag- bedside furniture had broken drawers- one kitchen chair was extremely wobbly- kitchen table light did not workWe will not staying here again."
The price is CA $153
CA $289 total
includes taxes & fees
Jul 28 - Jul 29
Modern Condo|DWNTN Hartord| XL Center| GYM

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Charming, Large Cozy 1-bedroom house in fabulous Berlin with WiFi, near Hartford

2.0 star property
10.0 out of 10, Exceptional, (1)
"I'd like to say that upon arriving the house was beautiful. There's a gorgeous backyard pond with a water spout in the middle. A nice accessible driveway and a cute little cobblestone walkway leading up to the entrance of the guest house. It was beautiful when we arrived inside. House was clean and inviting and there was also cold water and refreshments. Will 100% be booking again... I would give it a hundred stars if I could. Best experience ever."
Charming, Large Cozy 1-bedroom house in fabulous Berlin with WiFi, near Hartford

Amazing Waterfront Home in Branford Private Beach🏖 Panoramic Water Views+Hot Tub

9.8 out of 10, Exceptional, (65)
"We very much enjoyed our stay and were pleasantly surprised by how great the views were from practically every room in the house. Check-in was very simple and there were many nice touches awaiting us at the property. "
Amazing Waterfront Home in Branford Private Beach🏖 Panoramic Water Views+Hot Tub

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

10.0 out of 10, Exceptional, (16)
"I've stayed here multiple times and it was amazing as always. Great communication, clean, and beautiful! "
The price is CA $735
CA $1,213 total
includes taxes & fees
Jul 29 - Jul 30
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

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

10.0 out of 10, Exceptional, (63)
"Great location "
New Madison beach house - Ocean front- Great views- booking Summer 2025

Totally Private Cozy studio in awesome Hartford with WiFi, AC

9.0 out of 10, Wonderful, (6)
"I was a little worried to be right in downtown with just me and my daughter. But this location was very safe and cute shopping area around the apartment. "
The price is CA $148
CA $221 total
includes taxes & fees
Aug 3 - Aug 4
Totally Private Cozy studio in awesome Hartford with WiFi, AC

Angelica’s safe haven @ west haven

10.0 out of 10, Exceptional, (4)
"This place was perfect for our weekend trip to New Haven. Angelica was a great Host, and communicated timely and clear. I would stay again if I ever come back to New Haven. "
The price is CA $184
CA $446 total
includes taxes & fees
Aug 2 - Aug 3
Angelica’s safe haven @ west haven

Direct Waterfront Private Beach Escape

9.8 out of 10, Exceptional, (14)
"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
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

Frequently asked questions

Can I find a vacation rental in Cheshire?

Yes, we have vacation rentals in Cheshire close to Barker Character, Comic and Cartoon Museum, or you can select a more remote option if you'd like a relaxing place to stay. Our travelers say Cheshire has a good selection of restaurants. Make sure you have time to check out the waterfalls and shopping during your trip.

What are some of the best vacation home rentals in Cheshire?

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub : You might want to consider this vacation home rental near Cheshire, which is located on the beach and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Kick off your shoes and enjoy yourself with a garden and a hot tub.

How many vacation rentals are there in Cheshire?

Expedia has 3 vacation rentals for your stay in Cheshire.

What’s there to see and do in Cheshire?

Family-friendly attractions include Barker Character, Comic and Cartoon Museum and Cheshire Hollow Farm, whereas Roaring Brook Park and Drazen Orchards are a couple of great spots to enjoy the outdoors. While here, Maplecroft Plaza Shopping Center and Bartlem Park are other places worth a visit.

What’s a vacation rental in Cheshire like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Cheshire. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for family trips or small group gatherings.