Cheshire Vacation Rentals from $99: Search Short-Term Rentals

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Vacation Rentals in Cheshire

Cheshire Vacation Rental Travel Info

Number of vacation rentals	2
Popular accommodation	Cheshire private vacation homes
Known landmarks	Lake Compounce, Toyota Presents Oakdale Theatre and Powder Ridge Mountain Park and Resort
International airport	Hartford, CT (BDL-Bradley Intl.)

Other types of properties in Cheshire you may be interested in

"I wanted to give this hotel 4- to 5 stars. The staff were excellent. That said, this is an old property, with worn out rugs in halls, threadbare bedding and towels (mine had tears and holes), but nonetheless clean, and nearly arranged. The hotel is off a main highway, but local food choices did not work and what they had available was limited."

$144 total

includes taxes & fees

Jun 9 - Jun 10

"I was from 9pm to 9am each night. Otherwise I was away at graduation and reunion at the school where I taught from 1960 to 2004.The inn was very clean, comfortable, functional, and affordable: basics were good, not fancy and with few frills - KS bed, firm mattress, efficient heat/ac: clean but very basic bathroom {sink drain slow, satisfactory but not soft linen, tub clean without safety bars, good and sufficient lighting, desk w/.comfortable rolling & padded chair, small bedside cabinets4 ...

$88 total

includes taxes & fees

Jun 16 - Jun 17

"Old school charm"

$171 total

includes taxes & fees

Jun 30 - Jul 1

Everything you need to know about Cheshire vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cheshire vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cheshire vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cheshire vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cheshire. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cheshire in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $99 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cheshire rentals

At Expedia, we put the best Cheshire vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cheshire rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cheshire vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cheshire. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Cheshire?

Yes, we have vacation rentals in Cheshire close to Cheshire Hollow Farm, 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 spa 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 Cheshire Hollow Farm and Barker Character, Comic and Cartoon Museum, whereas Quinnipiac Recreation Area 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.