Cheshire Historic District Vacation Rentals

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Check prices for these dates

Tonight
Jul 25 - Jul 26
Tomorrow
Jul 26 - Jul 27
This weekend
Jul 25 - Jul 27
Next weekend
Aug 1 - Aug 3

Vacation Rentals in Cheshire Historic District

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, (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
Luxury Apartments by Hyatus at Pierpont
Seasonal outdoor pool

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 3 bedroom minutes from Yale and the beach
Private kitchen

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
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Interior

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

9.6 out of 10, Exceptional, (5)
"Great night stay! Wonderful place would definitely recommend! "
The price is ￥13,089
￥17,994 total
includes taxes & fees
Jul 28 - Jul 29
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Charming Historic 2BR Retreat in New Haven – Cozy Stay Near Yale & Downtown!
Exterior

Charming Historic 2BR Retreat in New Haven – Cozy Stay Near Yale & Downtown!

7.8 out of 10, Good, (7)
"Very nice property and close to the Shubert Theatre for my event. I would stay at the property again."
Charming Historic 2BR Retreat in New Haven – Cozy Stay Near Yale & Downtown!
StedleyCreek! One bed-room apartment in the Stoney Creek area of Branford, CT.
Terrace/patio

StedleyCreek! One bed-room apartment in the Stoney Creek area of Branford, CT.

2.0 star property
10.0 out of 10, Exceptional, (9)
"The property is clean ,comfortable tastefully decorated, convenient to many locations. Host communication is great! Highly recommend!"
StedleyCreek! One bed-room apartment in the Stoney Creek area of Branford, CT.
Cozy Lakefront Bungalow w firepit/dock/kayaks
Terrace/patio

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

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
Dining

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.
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, (16)
"I've stayed here multiple times and it was amazing as always. Great communication, clean, and beautiful! "
The price is ￥79,418
￥131,113 total
includes taxes & fees
Jul 29 - Jul 30
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Direct Waterfront Private Beach Escape
Outdoor dining

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
Luxury Furnished Apartments by Hyatus Downtown at Yale
Honeymoon Apartment, 3 Bedrooms, Kitchen | In-room dining

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
Angelica’s safe haven @ west haven
Exterior

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 ￥19,854
￥48,974 total
includes taxes & fees
Aug 1 - Aug 2
Angelica’s safe haven @ west haven
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Property grounds

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (34)
"Clean stunning views amazing host "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Modern 3BR ★ Fast Wi-Fi + Free Parking ★ Flexible Cancel Anytime! - 10 Mins WeHa
Fridge, microwave, oven, stovetop

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
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Beach nearby

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

9.6 out of 10, Exceptional, (10)
"Loved the feeling of being in a family cottage near the beautiful water and pretty old homes "
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Interior

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 ￥42,650
￥69,637 total
includes taxes & fees
Jul 28 - Jul 29
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (32)
"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
Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi
Fridge, microwave, oven, stovetop

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

Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Fridge, microwave, oven, stovetop

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 ￥13,898
￥25,690 total
includes taxes & fees
Jul 28 - Jul 29
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
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

Wyndham Southbury

Wyndham Southbury

10/10 Excellent
"This is a beautiful hotel nestled in the middle of forested hills of the interstate. The lobby is grand, and the rooms are large and comfortable. The 50" flat-screen tv is nice with lots of channels. The beds are very comfortable and the linens clean and bright white.the bathrooms are updated and bright, and the shower performed like a champ. I enjoyed the large swimming pool, especially at 6:00 am. A great syay, staff are friendly and helpful "
Howard 2-night trip
Posted 3 hours ago
Wyndham Southbury

Frequently asked questions

Can I find vacation rentals in Cheshire Historic District?

Yes, there are vacation rentals near popular sights in Cheshire Historic District, or you can go with a 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 vacation home rentals in Cheshire Historic District?

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub : This vacation home rental outside of Cheshire Historic District 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.

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 larger area, you’ll find Toyota Oakdale Theatre and Sleeping Giant State Park.

What are vacation rentals like in Cheshire Historic District?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Cheshire Historic District. Vacation rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family trip or a small group gathering.