A stone tower with a metal gate, surrounded by trees and a stone wall.

Cheshire Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Cheshire vacation rentals

Apartment (1 Bedroom) | Interior

1. Bristol Condo Near Espn HQ & Lake Compounce!

Bristol Condo Near Espn HQ & Lake Compounce!
3.5 star property
Bristol
The price is AED 643
AED 1,153 total
includes taxes & fees
1 Sep - 2 Sep
Bristol Condo Near Espn HQ & Lake Compounce!
Apartment, City View | Living area | 40-inch flat-screen TV with digital channels, Netflix, Hulu

2. Trumbull Apartments

Trumbull Apartments
3.0 star property
Downtown Hartford
The price is AED 711
AED 1,111 total
includes taxes & fees
12 Aug - 13 Aug
Trumbull Apartments
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

New Haven Hotel

New Haven Hotel

10/10 Excellent
"Clean and spacious room; and nice and helpful staff"
Min 1-night trip
Posted 1 hour ago
New Haven Hotel

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?

Cozy 1-bedroom house in lovely New Haven with AC close to Yale University: Visitors like this Cheshire vacation home rental. It is equipped with a patio, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

What’s there to see and do in Cheshire?

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