Cheshire Historic District Holiday Rentals

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Cheshire Historic District

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (1966)
"It is a great Apartment-hotel and the suites have the right amenities. One critic that I have would be that there would sometimes you could smell the cigarette smoke from other neighbours blowing into the furnace. Public transportation is limited and so it's best to have a car. Staff is super helpful and accommodating. "
The price is AU$174
includes taxes & fees
25 Nov - 26 Nov
New Haven Village Suites

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

10.0 out of 10, Exceptional, (126)
"We stayed here for an anniversary weekend away and found the property and neighborhood to be amazing. We enjoyed the hot tub, pool and firepit and went kayaking in the afternoon. Enjoyed amazing sunsets from the deck; Adam gave us spot-on restaurant recommendations. I don't know if the supply of snacks is standard or an anniversary "special", but all in all this place was a wonderful find. Thank you!!"
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.8 out of 10, Exceptional, (34)
"Great location! Clean building And modern. "
Luxury Furnished Apartments by Hyatus Downtown at Yale

Beautiful cozy rooms near hospital and down town area

8.0 out of 10, Very good, (17)
"I will forever love coming here. The host was great, Parking was amazing, Rooms were so cleanly. "
The price is AU$389
includes taxes & fees
25 Nov - 26 Nov
Beautiful cozy rooms near hospital and down town area

cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.

The price is AU$179
includes taxes & fees
25 Nov - 26 Nov
cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.

Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

10.0 out of 10, Exceptional, (58)
"Great"
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

Waterfront Cottage in Branford

10.0 out of 10, Exceptional, (87)
"The house was perfect for our annual getaway. We are a group of nine women who have been friends for over 45 years. The large well stocked kitchen with amazing view of the water and fireplace made our Friendsgiving meal memorable! The outdoor hot tub, fire pit, and deck with comfy seating topped off the weekend. Great location, plenty of parking, responsive host. 5/5 stars! "
Waterfront Cottage in Branford

lakefront estate

3.8 out of 10, (8)
"Overall do not stay in this house! They are scamming people! They say they are military family yet took advantage of one!! Still owe me my refund and refuse to answer VRBO to give the okay to refund my money! This place was not clean it was very unsanitary and there were drug paraphernalia in the backyard! Towels wet and dirty on the bathroom floor and one of the bedrooms the sheets were dirty in the floor claimed that the house keeper cleaned it! The pool was disgusting!! I have videos pictures...
lakefront estate

Beautiful 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (69)
"our annual girls (5) trip took us to Branford, CT this year. It was awesome to have a private beach access even though we couldn’t get in the water, but it was great for strolls and shell collecting. Would definitely do better with a second bathroom, but we managed just fine. Overall, it’s a nice little place to stay for a getaway. My only issue is not with the hosts or place, but with one of the fees and the checkout process. However, it does not take away from our stay. "
Beautiful 4BR Beach House with Private Beach Access.

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (26)
"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

The Dream Location for Your Perfect Vacation

9.8 out of 10, Exceptional, (16)
"beautiful quiet spot on the beach, great place to stay."
The Dream Location for Your Perfect Vacation

New Haven Gem w/ Private Pool, Walk to Beach!

9.6 out of 10, Exceptional, (4)
"In town for college visits we were able to stay and use the home as “base” giving everyone space - inside and out to decompress. Kitchen was great and outdoor space is lovely. Beautiful walk to Lighthouse Point Park!"
New Haven Gem w/ Private Pool, Walk to Beach!

Amazing Waterfront Home Private Beach 🏖+ Hot Tub

9.8 out of 10, Exceptional, (59)
"Overall the house was great. The beds were so so comfortable and the house has everything you need to cook and grill. Unfortunately weather wasn’t ideal but we still got to enjoy the hot tub and at least check out the private beach. The beach is across the street and it’s not too bad, just a lot of sharp shells so I’d rec wearing some sandals to and on the beach! The house is a lot bigger than we realized and beautiful views all around. Owner was great and responsive. The master was awesome and...
Amazing Waterfront Home Private Beach 🏖+ Hot Tub

Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger

9.4 out of 10, Exceptional, (6)
"There was 7 family members all had sleeping quarters. We enjoyed the location. The lake was beautiful went out on kayaks and enjoyed walks around the neighborhood. Sat outside and played games and enjoyed the fire. Nice weekend was had by all "
Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger

Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

10.0 out of 10, Exceptional, (46)
"The house was beautiful and a perfect place for our family to be at while visiting our daughter who is a student at Yale. We saw the sunrise over the ocean from our bedroom window. Wish we found this sooner!"
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

Historic Whitneyville Cottage

9.4 out of 10, Exceptional, (13)
"Road noise was annoying. Otherwise as advertised."
Historic Whitneyville Cottage

Guilford Carriage House at Granite Lodge!

10.0 out of 10, Exceptional, (8)
"We had a couple of out of town events in the are this past weekend, and it was also my birthday, so we decided to stay somplace special. The Granite Lodge Carriage hose was all of that! Beautifully decorated and furnished with lots of special touches from the host! We would definitely recommend, and will!"
Guilford Carriage House at Granite Lodge!

Guest Cottage on Country Estate

9.2 out of 10, Wonderful, (40)
"Beautiful cottage, spectacular property, wonderful hosts. Not sure what else to say? We came up to CT with our pup to look at areas we may want to move to. The cottage was perfect for us, nice and private and lots of land for our pup to walk. Great state park a few miles away and plenty of good restaurants nearby. Very happy!"
Guest Cottage on Country Estate

Fun Downtown Location 2nd flr

9.8 out of 10, Exceptional, (65)
"This property is a remodeled older house. With all that old house charm. It is spacious and has three bedrooms, each with a queen bed. The couch is extremely comfortable and it was great watching TV and sipping wine."
Fun Downtown Location 2nd flr

Private Home - Pool and Close to CT Shoreline Beaches

9.4 out of 10, Exceptional, (6)
"House was very clean and slept all 7 of us comfortably! Pool and firepit were nice to have and enjoy. Would absolutely book this house again if I ever needed. Just be sure to ignore the unkind neighbor signs, they don't reflect on the property at all. "
Private Home - Pool and Close to CT Shoreline Beaches
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.
Don't see what you're looking for?
See all available properties in Cheshire Historic District
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Cheshire Historic District you may be interested in

New Haven Hotel

3.5 star property
8.8 out of 10, Excellent, (1391)
"The staff friendly and helpful . Room was comfortable,quiet and clean ."
The price is AU$228
includes taxes & fees
20 Dec - 21 Dec
New Haven Hotel

Motel 6 New Haven - Branford, CT

2.0 star property
6.6 out of 10, (1071)
"Thanks "
The price is AU$124
includes taxes & fees
1 Dec - 2 Dec
Motel 6 New Haven - Branford, CT

Holiday Inn Express Southington, an IHG Hotel

2.5 star property
8.6 out of 10, Excellent, (1068)
"Nice place to rest your head, breakfast was lackluster, convenient location."
The price is AU$204
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn Express Southington, an IHG Hotel
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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 Crystal Bees, or get out into nature at a spot like Sleeping Giant State Park. In the wider area, you’ll find Toyota Oakdale Theatre and Mount Carmel.

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.