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Top Holiday Rentals in Cheshire Historic District

Cozy 3 bedroom minutes from Yale and the beach

7.4 out of 10, Good, (3)
"The inside was very clean, the back patio/garden area is cute, but the pool was green by day two. Overall we enjoyed our time here"
Cozy 3 bedroom minutes from Yale and the beach

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

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

10.0 out of 10, Exceptional, (136)
"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

Cozy 1-bedroom apartment in cool New Haven with WiFi, fitness room

The price is £228
includes taxes & fees
11 Aug - 12 Aug
Cozy 1-bedroom apartment in cool New Haven with WiFi, fitness room

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (35)
"Clean stunning views amazing host "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

Beachside Branford- walk to Beach, Grill

9.8 out of 10, Exceptional, (6)
"Charming little cottage that was just right for our trip to the CT shoreline."
Beachside Branford- walk to Beach, Grill

Cute and comfy condo

Cute and comfy condo

Gorgeous 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (74)
"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."
Gorgeous 4BR Beach House with Private Beach Access.

Modern 3BR ★ Fast Wi-Fi + Free Parking ★ Flexible Cancel Anytime! - 10 Mins WeHa

2.0 star property
6.6 out of 10, (4)
"Communication with the host was excellent. His place was clean, bright, and very well equipped! The location makes it easy to get around the greater Hartford area. Our stay was very good!"
Modern 3BR ★ Fast Wi-Fi + Free Parking ★ Flexible Cancel Anytime! - 10 Mins WeHa

Modern Luxury, The Perfect Getaway Awaits

10.0 out of 10, Exceptional, (2)
"Super clear, spacious, house looks just like the photos. Very easy communication with the host. Thank you!"
The price is £375
includes taxes & fees
11 Aug - 12 Aug
Modern Luxury, The Perfect Getaway Awaits

Cozy Lakefront Bungalow w firepit/dock/kayaks

10.0 out of 10, Exceptional, (29)
"This is our second time visiting the area and staying at this beautiful home. It's close to many activities for children and adults, easy to access food and services and a beautiful overall area and home. We truly enjoy visiting!"
Cozy Lakefront Bungalow w firepit/dock/kayaks

Beach Bungalow, walk to beach, private backyard

10.0 out of 10, Exceptional, (3)
"The property was perfect for all of us. It was in a quiet neighborhood and great location."
Beach Bungalow, walk to beach, private backyard

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.6 out of 10, Exceptional, (51)
"Great location, great stay!"
Luxury Furnished Apartments by Hyatus Downtown at Yale

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

10.0 out of 10, Exceptional, (18)
"I've stayed here multiple times and it was amazing as always. Great communication, clean, and beautiful! "
The price is £620
includes taxes & fees
13 Aug - 14 Aug
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

Spacious 3-bedroom apartment with WiFi, AC in fabulous New Haven

7.0 out of 10, Good, (2)
"It was very clean "
Spacious 3-bedroom apartment with WiFi, AC in fabulous New Haven

4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy

10.0 out of 10, Exceptional, (33)
"We went for a family vacation and we had a great time - location is close to lots of great places - house was clean and very roomy"
4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy

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 £133
includes taxes & fees
13 Aug - 14 Aug
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi

Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

9.6 out of 10, Exceptional, (13)
"The apartment was beautiful. One highlight for the children was the arcade game in the living room. The view of the water was striking from the living room and bedroom. The neighborhood was very quiet. Shakeema was a great host, easy to contact and she responds quickly. Thank you! I would recommend this VRBO to family and friends."
The price is £323
includes taxes & fees
11 Aug - 12 Aug
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF

9.8 out of 10, Exceptional, (120)
"Very responsive owner in beautiful place! We enjoyed our time here."
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
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 Historic District Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Cheshire Historic District?

Yes, there are holiday rentals close to the most popular sights in Cheshire Historic District, or you can select a more secluded option if you're looking for a relaxing stay. Cheshire Historic District is known for its churches and university setting.

What are some of the best holiday rentals that Cheshire Historic District has to offer?

Cozy 3 bedroom minutes from Yale and the beach: This holiday home rental outside of Cheshire Historic District is located near the beach, and offers a BBQ, air conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Cheshire Historic District?

Explore the area and family-friendly sights such as Lake Compounce, or get out into nature at a spot like Mount Carmel. In the wider area, you’ll find Toyota Oakdale Theatre and Sleeping Giant State Park.

What are holiday rentals like in Cheshire Historic District?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cheshire Historic District. Holiday rentals offer extras like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for families.