Cheshire Vacation Rentals from $196: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Cheshire vacation rentals

Apartment in Cheshire

Robert S.

$183 nightly

Mar 26 - Mar 27

Total with taxes and fees

Vacation Home in Wallingford Center

Jeanette W.

$273 nightly

Mar 10 - Mar 11

Total with taxes and fees

Vacation Home in Middletown

Brooke

$189 nightly

Mar 10 - Mar 11

Total with taxes and fees

Smart TV, fireplace, books, music library

Apartment in Haddam

Glenna M.

$223 nightly

Mar 16 - Mar 17

Total with taxes and fees

Apartment in Southington

Ryan A.

$302 nightly

Mar 10 - Mar 11

Total with taxes and fees

Apartment in West Haven

Veronica

$283 nightly

Mar 10 - Mar 11

Total with taxes and fees

Apartment in Wallingford Center

Nadine C.

1 bedroom, iron/ironing board, WiFi, bed sheets

Apartment in Dwight

Michael H.

$240 nightly

Mar 10 - Mar 11

Total with taxes and fees

Apartment in Wallingford Center

David S.

$284 nightly

Mar 10 - Mar 11

Total with taxes and fees

Vacation Home in East Shore

Leilani R.

$485 nightly

Mar 16 - Mar 17

Total with taxes and fees

Apartment in Dwight

"The studio apartment is in a very convenient location. It is a lovely walk to Yale. Many restaurants just outside the door. My friends, who joined me for a meal, found parking easily. It was a plus having use of a parking pass for Dwight Street. We never had a problem getting a parking spot. We also loved being able to bring our two small pups with us. The bottle of wine was a thoughtful touch. "

ELIZABETH M S M.

$218 nightly

Mar 10 - Mar 11

Total with taxes and fees

Vacation Home in Fair Haven

Brian B.

$273 nightly

Mar 10 - Mar 11

Total with taxes and fees

Cabin in Bethlehem

Jennifer Y.

$371 nightly

Mar 10 - Mar 11

Total with taxes and fees

Vacation Home in The Hill

Peterson

$137 nightly

Mar 10 - Mar 11

Total with taxes and fees

Desk, iron/ironing board, WiFi, bed sheets

Apartment in Dwight

Jeffrey C.

$180 nightly

Mar 10 - Mar 11

Total with taxes and fees

Vacation Home in Mill River

Lawrence

$195 nightly

Mar 10 - Mar 11

Total with taxes and fees

Apartment in West New Haven

Joan S.

$200 nightly

Mar 15 - Mar 16

Total with taxes and fees

Apartment in East Rock

Denyce D.

$334 nightly

Mar 14 - Mar 15

Total with taxes and fees

Vacation Home in Fair Haven

Jamie S.

$205 nightly

Mar 10 - Mar 11

Total with taxes and fees

Vacation Home in West Haven

Joseph T.

$462 nightly

Mar 10 - Mar 11

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Cottages

Cabins

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Cheshire Hotel Reviews

Cambria Hotel New Haven University Area

4/10 Poor

"Hotel staff not the most friendly nor helpful. Paid almost $100 for parking for 3 nights and stayed over by an hour and had to pay an additional amount since parking is only through check out time. Furthermore the room wasn’t even the most cleanliness, traces of hair throughout the room and bedding. Mold and mildew in the shower, low water pressure, and broken shower door. When brought it to the front desk attention was told they’ll look into it and never heard anything back. Only thing that was good about this hotel was the location but don’t think I would ever stay here again."

The Capitol Hotel

2/10 Terrible

"I travel frequently and am comfortable staying in modest hotels as long as they are clean and safe. Unfortunately, The Capitol Hotel in Hartford raised serious safety concerns and appears to be significantly misrepresented online. The property does not resemble the photos on Expedia. The exterior is extremely run down, and the covered entrance had large holes in the roof with exposed pipes and roofing material hanging down, giving the immediate impression that the building is poorly maintained. My daughter arrived around 11 PM after a late flight. When she entered the lobby there were multiple people sleeping on the floor and in chairs, and she overheard the front desk telling someone without a room that they could sleep in the lobby for the night. This did not feel like a safe or properly managed environment for guests arriving late at night. While the room appeared old but generally clean, the bed was two box springs with only a thin mattress topper instead of a proper mattress, which is completely unacceptable and clearly not what is represented online. The listing also advertises a fitness center, but the front desk confirmed there is no gym. The television only received one channel. These issues reflect clear misrepresentation of the amenities advertised on Expedia. When I arrived the next morning, I was so concerned by the property conditions that we immediately checked out and left. Travelers should be aware that the actual conditions of this property"

Find out more about Cheshire

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 $196 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.

Explore a world of travel with Expedia

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?

A spacious TREETOPS Reunion/ Retreat/Event venue! Sleeps 10-12. Seasonal POOL!: Visitors like this Cheshire vacation home rental. It is located in the city center and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of books so you can immerse yourself in your vacation.

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 Bartlem Park are a couple of great spots to enjoy the outdoors. While here, Maplecroft Plaza Shopping Center and Drazen Orchards 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.

Cheshire Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Cheshire vacation rentals

Apartment in Cheshire

Vacation Home in Wallingford Center

Vacation Home in Middletown

Apartment in Haddam

Apartment in Southington

Apartment in West Haven

Apartment in Wallingford Center

Apartment in Dwight

Apartment in Wallingford Center

Vacation Home in East Shore

Apartment in Dwight

Vacation Home in Fair Haven

Cabin in Bethlehem

Vacation Home in The Hill

Apartment in Dwight

Vacation Home in Mill River

Apartment in West New Haven

Apartment in East Rock

Vacation Home in Fair Haven

Vacation Home in West Haven

The Annual Vacation Sale

Find vacation rentals that suit your style

Top Cheshire Hotel Reviews

Cambria Hotel New Haven University Area

Find out more about Cheshire

Explore a world of travel with Expedia

Trending destinations on Expedia.com

Frequently asked questions

Expedia's Latest Trends

Go further with the Expedia app