Cheshire Historic District Holiday Rentals : Search Short-Term Rentals

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Holiday Rentals in Cheshire Historic District

Enjoy a refreshing dip in the pool surrounded by a deck and basketball hoop.

"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! "

Relax by the rooftop pool with a stunning city view, surrounded by lounge chairs and a railing.

"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."

Kitchen features a central island, oven, and white cabinetry with a patterned backsplash.

"Would recommend. It was quaint second story apartment in an older home. Nicely updated."

Stunning two-story home with a central entrance, double doors, and a charming porch.

"Very nice property and close to the Shubert Theatre for my event. I would stay at the property again."

Enjoy meals in this kitchen with a microwave, stainless steel range hood, and dining area with a table and chairs.

"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!"

Enjoy the view from the upper balcony, which offers a fire pit and Adirondack chairs in the yard.

"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!"

Enjoy a city view from the large window, with a dining table and chairs, a sofa, and a side table.

"Great location, great stay!"

Relax by the fire pit in a serene outdoor seating area surrounded by Adirondack chairs.

"My friends and stayed for a night. The house is nice and the owners is very communicative. "

includes taxes & fees

23 Jul - 24 Jul

Relax in style with a comfortable sofa, small table, and barbecue grill in this modern outdoor space.

"What a great place. We will be back!"

includes taxes & fees

21 Jul - 22 Jul

"Place was so cute and spacious. Owner was awesome too! Definitely recommend."

includes taxes & fees

20 Jul - 21 Jul

Enjoy a peaceful lakeside retreat with a dock, table, and chairs, surrounded by lush grass and a shaded tree.

"Clean stunning views amazing host "

Relax in this inviting living space with a comfortable sofa, coffee table, and scenic forest views.

"I have stayed here multiple times because I love it so much and it's amazing as always! Beautiful house, so clean, and great communication with Chad! "

includes taxes & fees

29 Jul - 30 Jul

Enjoy cooking in this well-equipped kitchen with a central island and stainless steel appliances.

"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"

Enjoy ocean views from this deck with a flat roof and covered seating area.

"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! "

Compact kitchen with modern cabinetry, oven, and stovetop, offering versatile cooking options.

"Overall, this property is honestly one of the nicest homes I’ve stayed at. The kitchen was nice and big and the bathroom was so pretty. I enjoyed my stay it was very nice and would love to come and stay again. I recommend this home !! The neighbor is also very nice ! they helped me find my parking spot! ❤️"

includes taxes & fees

20 Jul - 21 Jul

Relax in a warm and inviting space with a hot tub, wicker furniture, and large windows.

"The host was very kind and responsive, which we truly appreciated. However, the house was not properly cleaned. There were a lot of flies inside, the basement had a strong musty smell, and the hot tub water was untreated and had a bad odor, With better cleaning, maintenance, and care for the house the stay could have been much more pleasant."

Classic brick building with ornate metal stairs and a small garden area.

"Great studio, worked well for our stay to attend Yale Commencement. The location is convenient to campus with multiple close dining options. Well appointed space with everything necessary for a comfortable stay. There are shared laundry and kitchen areas….be mindful of that if you’re planning to cook meals, there is no kitchen in the unit but it does have an under counter refrigerator and a small sink.We would recommend a stay here, it’s very convenient and comfortable!"

Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and oven, complemented by white cabinetry and a skylight above the island.

Enjoy a meal or relax with friends on the deck, surrounded by a lush yard and trees.

"Excellent place in an excellent location. Charles is a wonderful host. Will be staying there again. "

Guests can enjoy access to a tranquil beach with calm waters.

"Loved the feeling of being in a family cottage near the beautiful water and pretty old homes "

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

Sign in

Sign up, it's free

Top Cheshire Historic District Hotel Reviews

Find out more about Cheshire Historic District

Everything you need to know about Cheshire Historic District holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cheshire Historic District holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 Historic District holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cheshire Historic District holiday rentals: An excellent choice for every season

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cheshire Historic District holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cheshire Historic District holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cheshire Historic District rentals

At Expedia, we put the best Cheshire Historic District holiday 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 Historic District 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 Historic District holiday.

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 Historic District. 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 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?

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub : This holiday home rental outside of Cheshire Historic District is located on the beach, and has an outdoor pool, a balcony and a BBQ 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 1 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 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.

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Holiday Rentals in Cheshire Historic District

Change your mind

Treat yourself

Be picky

Check prices for these dates

Holiday Rentals in Cheshire Historic District

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

Luxury Apartments by Hyatus at Pierpont

Cozy 3 bedroom minutes from Yale and the beach

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

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

Cozy Lakefront Bungalow w firepit/dock/kayaks

Luxury Furnished Apartments by Hyatus Downtown at Yale

Tranquil Litchfield Connecticut Retreat".

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

Heavenly Home in New Haven /5 mins drive from Yale

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

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

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

Direct Waterfront Private Beach Escape

Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment

Spacious Woodbury Home w/ Pool + Hot Tub!

Charming Studio| Near Yale| Downtown New Haven

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

New One Bedroom Apartment Centrally Located in Southbury

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

Top Cheshire Historic District Hotel Reviews

Find out more about Cheshire Historic District

Frequently asked questions