Cheshire Historic District Holiday Rentals

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Holiday 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

Charming Studio| Near Yale| Downtown New Haven

9.0 out of 10, Wonderful, (4)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
The price is AU$321
includes taxes & fees
29 Sept - 30 Sept
Charming Studio| Near Yale| Downtown New Haven

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

9.4 out of 10, Exceptional, (14)
"This Carriage House is exactly as described. Wonderful location and setting, just steps away from Branford Point. Hope to visit again soon! "
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

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

6.8 out of 10, (3)
"Good communication with the manager, quiet place and extremely clean. I enjoyed it"
The price is AU$283
includes taxes & fees
1 Oct - 2 Oct
New Furnished Apt in West Hartford w/ Parking and Central AC

Stunning Apt W/ Parking and Gym | Downtown at Yale

10.0 out of 10, Exceptional, (42)
"High quality experience, walking distance to all we needed, clean and spacious. Excellent support and communication from the hosts, would stay again."
Stunning Apt W/ Parking and Gym | Downtown at Yale

Luxury Apartments by Hyatus at Pierpont

4.0 star property
9.4 out of 10, Exceptional, (20)
"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

McAngel Haven: 5 mins from Yale

9.6 out of 10, Exceptional, (14)
"My family and I stayed at the property for a wedding in Milford. The house had plenty of space for our group to say, and the bedrooms were comfortable. The three bathrooms were helpful for our group to efficiently get ready for the wedding, and the kitchen was adequately appointed for us to have meals."
The price is AU$800
includes taxes & fees
5 Oct - 6 Oct
McAngel Haven: 5 mins from Yale

Conference Room Rental no sleeping arrangements

The price is AU$1,411
includes taxes & fees
27 Sept - 28 Sept
Conference Room Rental no sleeping arrangements

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

10.0 out of 10, Exceptional, (3)
"Great stay at this lovely house. Walk to beach! Perfect backyard to enjoy a beautiful weekend "
Modern Beach Home - Waterview, close to restaurants, universities and hospitals

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

10.0 out of 10, Exceptional, (5)
The price is AU$434
includes taxes & fees
28 Sept - 29 Sept
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds

Cozy Safe Home

The price is AU$501
includes taxes & fees
29 Sept - 30 Sept
Cozy Safe Home

Yale Casa Verde Studio

10.0 out of 10, Exceptional, (5)
"The apartment was very comfortable , clean and close to the university. "
The price is AU$319
includes taxes & fees
30 Sept - 1 Oct
Yale Casa Verde Studio

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

9.8 out of 10, Exceptional, (68)
"Great family get together where we all were very comfortable. "
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

Cozy Two Bedroom Stay In Downtown New Haven!

The price is AU$499
includes taxes & fees
1 Oct - 2 Oct
Cozy Two Bedroom Stay In Downtown New Haven!

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

10.0 out of 10, Exceptional, (144)
"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

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

The price is AU$466
includes taxes & fees
30 Sept - 1 Oct
Chic 1-bedroom apartment with WiFi, fitness room in cool New Haven

Angelica’s safe haven @ west haven

10.0 out of 10, Exceptional, (5)
"Quiet place with spacious living room perfect for movie nights. Also just a 10-minute drive from the beach and multiple dining options. Host was very accommodating and communicative. Would stay here again."
The price is AU$513
includes taxes & fees
30 Sept - 1 Oct
Angelica’s safe haven @ west haven

Family Gem on Dyer Street

10.0 out of 10, Exceptional, (1)
"The check in process was simple and easy. The house was exactly as pictured and perfect for 7 guests. It was clean and had all the amenities."
The price is AU$1,464
includes taxes & fees
28 Sept - 29 Sept
Family Gem on Dyer Street

Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area

10.0 out of 10, Exceptional, (5)
"Everything was amazing "
Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area

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

10.0 out of 10, Exceptional, (19)
"I've stayed here multiple times and it was amazing as always. Great communication, clean, and beautiful! "
The price is AU$1,441
includes taxes & fees
26 Sept - 27 Sept
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
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 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, 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 favourite 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 depend 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 AU$283 per night. Entering your travel dates in the search wizard might find you 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?

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!: This holiday home rental outside of Cheshire Historic District is located near the beach, and has a selection of games, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, 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 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.