Cheshire Historic District Vacation Rentals

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Vacation Rentals in Cheshire Historic District

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.6 out of 10, Exceptional, (54)
"Loved the property and we will surely be coming back."
Luxury Furnished Apartments by Hyatus Downtown at Yale

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

9.8 out of 10, Exceptional, (12)
"Beautiful area, close to the beach, with a wonderfully kept house."
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

Modern Beach Home - Waterview, close to restaurants, universities and hospitals

10.0 out of 10, Exceptional, (1)
"The check in process was very easy. The home was airy and bright. My family and I felt the peace and relaxation of the home. The kitchen was large and clean."
Modern Beach Home - Waterview, close to restaurants, universities and hospitals

Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

9.8 out of 10, Exceptional, (66)
"We very much enjoyed our stay and were pleasantly surprised by how great the views were from practically every room in the house. Check-in was very simple and there were many nice touches awaiting us at the property. "
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

Cozy 1-bedroom apartment in cool New Haven with WiFi, fitness room

2.0 out of 10, (1)
"Host never emailed info. After numerous attempts to contact them, we gave up and stayed in a hotel. VRBO gave full refund. I don’t recommend this host, but VRBO was great!"
The price is CA $211
CA $417 total
includes taxes & fees
Sep 6 - Sep 7
Cozy 1-bedroom apartment in cool New Haven with WiFi, fitness room

Cozy Country Cottage

2.0 star property
9.0 out of 10, Wonderful, (7)
"Very accommodating and understanding host.They are warm and willing to listen and make your stay as comfortable as possible. Trent and his family will go out of their way to make the stay memorable.. I would highly recommend the stay at this accommodation to everyone. A home away from home."
The price is CA $206
CA $362 total
includes taxes & fees
Sep 7 - Sep 8
Cozy Country Cottage

Charming Studio| Near Yale| Downtown New Haven

10.0 out of 10, Exceptional, (3)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
The price is CA $153
CA $300 total
includes taxes & fees
Sep 8 - Sep 9
Charming Studio| Near Yale| Downtown New Haven

Yale Casa Verde Studio

10.0 out of 10, Exceptional, (4)
"Had a great stay!"
The price is CA $137
CA $292 total
includes taxes & fees
Sep 7 - Sep 8
Yale Casa Verde Studio

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

10.0 out of 10, Exceptional, (143)
"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! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

New Furnished Apt in West Hartford w/ Parking and Central AC

9.0 out of 10, Wonderful, (2)
"Good communication with the manager, quiet place and extremely clean. I enjoyed it"
The price is CA $87
CA $239 total
includes taxes & fees
Sep 7 - Sep 8
New Furnished Apt in West Hartford w/ Parking and Central AC

McAngel Haven: 5 mins from Yale

9.6 out of 10, Exceptional, (14)
"Had a wonderful but short stay in New Haven. Home.of PEZ and PIZZA . "
The price is CA $317
CA $727 total
includes taxes & fees
Sep 7 - Sep 8
McAngel Haven: 5 mins from Yale

Angelica’s safe haven @ west haven

10.0 out of 10, Exceptional, (4)
"This place was perfect for our weekend trip to New Haven. Angelica was a great Host, and communicated timely and clear. I would stay again if I ever come back to New Haven. "
The price is CA $189
CA $465 total
includes taxes & fees
Sep 7 - Sep 8
Angelica’s safe haven @ west haven

Seven Sleeps + Patio retreat/lake + Two-in-one game table/PS5

6.0 out of 10, (2)
"This place was very clean and Michael was great, answering all my questions quickly. check in was simple just a code to get in it was very updated and the beds were very comfortable. It was close to Yale and to some great pizza places"
The price is CA $201
CA $507 total
includes taxes & fees
Sep 8 - Sep 9
Seven Sleeps + Patio retreat/lake + Two-in-one game table/PS5

Direct waterfront cottage on private sandy beach

10.0 out of 10, Exceptional, (6)
"Enjoyed our stay very much. Cute cottage, rustic. Only downside was the airport is close "
Direct waterfront cottage on private sandy beach

Ranch style living at its best with country garden & patio!

9.6 out of 10, Exceptional, (13)
"Solid location and quiet neighborhood good after a long day."
Ranch style living at its best with country garden & patio!

Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds

10.0 out of 10, Exceptional, (2)
" Heck-on was smooth and the kitchen and facilities were great. "
The price is CA $211
CA $404 total
includes taxes & fees
Sep 22 - Sep 23
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds

Conference Room Rental no sleeping arrangements

The price is CA $993
CA $1,284 total
includes taxes & fees
Sep 7 - Sep 8
Conference Room Rental no sleeping arrangements

Family Gem on Dyer Street

The price is CA $597
CA $1,295 total
includes taxes & fees
Sep 7 - Sep 8
Family Gem on Dyer Street

Direct Waterfront Private Beach Escape

9.6 out of 10, Exceptional, (18)
"Thank you so Much, the family had a great time. Found some good seaglass"
Direct Waterfront Private Beach Escape

Luxury Apartments by Hyatus at Pierpont

4.0 star property
9.4 out of 10, Exceptional, (19)
"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
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 Historic District Hotel Reviews

Find out more about Cheshire Historic District

Find out more about Cheshire Historic District

Everything you need to know about Cheshire Historic District 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 Historic District vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cheshire Historic District vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cheshire Historic District vacation rentals we have selected for you start as low as CA $87 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 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 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 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 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 vacation rentals in Cheshire Historic District?

Yes, there are vacation rentals near popular sights in Cheshire Historic District, or you can go with a 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 vacation home rentals in Cheshire Historic District?

Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds: This vacation home rental outside of Cheshire Historic District has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

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 larger area, you’ll find Toyota Oakdale Theatre and Sleeping Giant State Park.

What are vacation rentals like in Cheshire Historic District?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Cheshire Historic District. Vacation rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family trip or a small group gathering.