Holiday Rentals in Cheshire Historic District

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Check prices for these dates

Tonight
11 Jul - 12 Jul
Tomorrow
12 Jul - 13 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

Holiday Rentals in Cheshire Historic District

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Enjoy a refreshing dip in the pool surrounded by a deck and basketball hoop.

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

10.0 out of 10, Exceptional, (132)
"My husband and I had a wonderful time at this idyllic cottage on the water in Branford. Great location and hosts. Beautiful community for long walks, restaurants nearby. Highly recommend! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Luxury Apartments by Hyatus at Pierpont
Relax by the rooftop pool with a stunning city view, surrounded by lounge chairs and a railing.

Luxury Apartments by Hyatus at Pierpont

4.0 star property
9.4 out of 10, Exceptional, (18)
"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
Charming Historic 2BR Retreat in New Haven – Cozy Stay Near Yale & Downtown!
Stunning two-story home with a central entrance, double doors, and a charming porch.

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

8.8 out of 10, Excellent, (6)
"We enjoyed our stay at this property. There was lots of room for us to gather and spend time together. The hosts were super helpful when we had any questions or issues and went out of their way to make our stay enjoyable. The property was close to Yale and the freeway, which made it easy to get around. The house was well appointed with everything we needed and was a great deal for the price. "
Charming Historic 2BR Retreat in New Haven – Cozy Stay Near Yale & Downtown!
Cozy 3 bedroom minutes from Yale and the beach
Kitchen features a central island, oven, and white cabinetry with a patterned backsplash.

Cozy 3 bedroom minutes from Yale and the beach

Cozy 3 bedroom minutes from Yale and the beach
Cozy Lakefront Bungalow w firepit/dock/kayaks
Enjoy the view from the upper balcony, which offers a fire pit and Adirondack chairs in the yard.

Cozy Lakefront Bungalow w firepit/dock/kayaks

10.0 out of 10, Exceptional, (27)
"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
Tranquil Litchfield Connecticut Retreat".
Relax by the fire pit in a serene outdoor seating area surrounded by Adirondack chairs.

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (14)
"My friends and stayed for a night. The house is nice and the owners is very communicative. "
The price is €277
includes taxes & fees
23 Jul - 24 Jul
Tranquil Litchfield Connecticut Retreat".
Luxury Furnished Apartments by Hyatus Downtown at Yale
Enjoy a city view from the large window, with a dining table and chairs, a sofa, and a side table.

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.6 out of 10, Exceptional, (50)
"Great location, great stay!"
Luxury Furnished Apartments by Hyatus Downtown at Yale
Heavenly Home in New Haven /5 mins drive from Yale
Fridge, microwave, oven, stovetop

Heavenly Home in New Haven /5 mins drive from Yale

9.0 out of 10, Wonderful, (19)
"Place was so cute and spacious. Owner was awesome too! Definitely recommend."
The price is €896
includes taxes & fees
13 Jul - 14 Jul
Heavenly Home in New Haven /5 mins drive from Yale
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Enjoy a peaceful lakeside retreat with a dock, table, and chairs, surrounded by lush grass and a shaded tree.

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (33)
"We stayed at the property for 2 nights and it was just what we had hoped. We enjoyed the lake, the fall colors and the house thoroughly. Would love to come back someday. "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Relax in this inviting living space with a comfortable sofa, coffee table, and scenic forest views.

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

10.0 out of 10, Exceptional, (16)
"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! "
The price is €660
includes taxes & fees
21 Jul - 22 Jul
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Spacious Woodbury Home w/ Pool + Hot Tub!
Relax in a warm and inviting space with a hot tub, wicker furniture, and large windows.

Spacious Woodbury Home w/ Pool + Hot Tub!

8.0 out of 10, Very good, (1)
"We rented this place for the first time for a family gathering. The setting was very private and “country-ish”. For the most part everything listed was present at the place and there were enough sleeping options for our crew. Overall - the owners were nice and fairly responsive but there was a level of disappointment to the care of the property and more importantly the preparedness for our arrival. They said the pool and hot tub were cleaned and ready but the pool was still dirty and the hot tub...
Spacious Woodbury Home w/ Pool + Hot Tub!
Direct Waterfront Private Beach Escape
Enjoy ocean views from this deck with a flat roof and covered seating area.

Direct Waterfront Private Beach Escape

9.8 out of 10, Exceptional, (13)
"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
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
Compact kitchen with modern cabinetry, oven, and stovetop, offering versatile cooking options.

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

7.6 out of 10, Good, (7)
"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! ❤️"
The price is €285
includes taxes & fees
12 Jul - 13 Jul
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
New One Bedroom Apartment Centrally Located in Southbury
Enjoy a meal or relax with friends on the deck, surrounded by a lush yard and trees.

New One Bedroom Apartment Centrally Located in Southbury

9.8 out of 10, Exceptional, (6)
"Excellent place in an excellent location. Charles is a wonderful host. Will be staying there again. "
The price is €140
includes taxes & fees
9 Aug - 10 Aug
New One Bedroom Apartment Centrally Located in Southbury
Charming Studio| Near Yale| Downtown New Haven
Classic brick building with ornate metal stairs and a small garden area.

Charming Studio| Near Yale| Downtown New Haven

10.0 out of 10, Exceptional, (3)
"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!"
The price is €186
includes taxes & fees
13 Jul - 14 Jul
Charming Studio| Near Yale| Downtown New Haven
Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and oven, complemented by white cabinetry and a skylight above the island.

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

Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Guests can enjoy access to a tranquil beach with calm waters.

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

9.8 out of 10, Exceptional, (8)
"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!
Relax by the River | Branford Waterfront Home
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and a large window offering a view of the outdoors.

Relax by the River | Branford Waterfront Home

8.8 out of 10, Excellent, (3)
"Clean, family friendly, and fun."
Relax by the River | Branford Waterfront Home
Modern Luxury, The Perfect Getaway Awaits
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and a dining area.

Modern Luxury, The Perfect Getaway Awaits

10.0 out of 10, Exceptional, (1)
The price is €463
includes taxes & fees
13 Jul - 14 Jul
Modern Luxury, The Perfect Getaway Awaits
Cozy, year round beachside cottage just steps to the water
Relax in this inviting living space with a comfortable sofa, coffee table, and bookshelf, perfect for unwinding. Enjoy a well-equipped kitchen and open architecture.

Cozy, year round beachside cottage just steps to the water

10.0 out of 10, Exceptional, (16)
"The house was beautiful, immaculate and right on the water. I’ve never had better price to value in a rental. Sheila was extremely accommodating and I would highly recommend!"
Cozy, year round beachside cottage just steps to the water
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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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.