Cheshire Historic District Vacation Rentals

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Vacation Rentals in Cheshire Historic District

Luxury Furnished Apartments by Hyatus Downtown at Yale
Honeymoon Apartment, 3 Bedrooms, Kitchen | In-room dining

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.6 out of 10, Exceptional, (55)
"Loved our stay here. "
Luxury Furnished Apartments by Hyatus Downtown at Yale
Charming Studio| Near Yale| Downtown New Haven
Exterior

Charming Studio| Near Yale| Downtown New Haven

9.2 out of 10, Wonderful, (5)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
$209 nightly
The price is $209
Oct 6 - Oct 7
Total with taxes and fees
Charming Studio| Near Yale| Downtown New Haven
Luxury Apartments by Hyatus at Pierpont
Seasonal outdoor pool

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
Private Apartment in Berlin
Fridge, microwave, oven, stovetop

Private Apartment in Berlin

2.0 star property
9.2 out of 10, Wonderful, (5)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
$279 nightly
The price is $316
Oct 5 - Oct 6
Total with taxes and fees
Private Apartment in Berlin
3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay
3 bedrooms, iron/ironing board, WiFi, bed sheets

3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay

7.0 out of 10, Good, (2)
"My son and I booked this property last minute. The owner was very quick to get back to us. It was very clean and had everything we needed. We would definitely stay there again."
$248 nightly
The price is $281
Oct 8 - Oct 9
Total with taxes and fees
3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay
Stunning Apt W/ Parking and Gym | Downtown at Yale
Interior

Stunning Apt W/ Parking and Gym | Downtown at Yale

10.0 out of 10, Exceptional, (44)
"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
Conference Room Rental no sleeping arrangements
Interior

Conference Room Rental no sleeping arrangements

$820 nightly
The price is $928
Oct 2 - Oct 3
Total with taxes and fees
Conference Room Rental no sleeping arrangements
New Cozy 2BR Stay New Haven Close to Yale
Fridge, microwave, oven, stovetop

New Cozy 2BR Stay New Haven Close to Yale

2.0 star property
7.4 out of 10, Good, (3)
"Place was great for family and having a washer and dryer was a big help. Place was super clean and comfortable "
$223 nightly
The price is $232
Oct 5 - Oct 6
Total with taxes and fees
New Cozy 2BR Stay New Haven Close to Yale
Cozy Safe Home
Fridge, microwave, oven, stovetop

Cozy Safe Home

$319 nightly
The price is $361
Oct 2 - Oct 3
Total with taxes and fees
Cozy Safe Home
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Beach nearby

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

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!
Fridge, microwave, oven, stovetop

Cozy Two Bedroom Stay In Downtown New Haven!

10.0 out of 10, Exceptional, (1)
"Exactly as advertised and had nice personal touches. Very close to attractions and very walkable. "
$296 nightly
The price is $305
Oct 2 - Oct 3
Total with taxes and fees
Cozy Two Bedroom Stay In Downtown New Haven!
Angelica’s safe haven @ west haven
Exterior

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."
$296 nightly
The price is $335
Oct 7 - Oct 8
Total with taxes and fees
Angelica’s safe haven @ west haven
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds
TV

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

10.0 out of 10, Exceptional, (5)
$256 nightly
The price is $290
Oct 5 - Oct 6
Total with taxes and fees
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds
Luxurious 3BR Apartment with Premium Amenities
Smart TV, video games, table tennis, books

Luxurious 3BR Apartment with Premium Amenities

10.0 out of 10, Exceptional, (16)
"The property was great- amenities like linens, decor, kitchen items were high quality. Great view also!"
Luxurious 3BR Apartment with Premium Amenities
Family Gem on Dyer Street
Dining

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."
$868 nightly
The price is $983
Oct 6 - Oct 7
Total with taxes and fees
Family Gem on Dyer Street
Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area
Exterior

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

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

$269 nightly
The price is $304
Oct 3 - Oct 4
Total with taxes and fees
Chic 1-bedroom apartment with WiFi, fitness room in cool New Haven
McAngel Haven: 5 mins from Yale
Fridge, microwave, oven, stovetop

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."
$454 nightly
The price is $515
Oct 5 - Oct 6
Total with taxes and fees
McAngel Haven: 5 mins from Yale
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Fridge, microwave, oven, stovetop

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

9.4 out of 10, Exceptional, (8)
"Needed a place to sleep for a couple of nights and this worked for us."
$155 nightly
The price is $175
Oct 2 - Oct 3
Total with taxes and fees
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
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

New Haven Hotel

New Haven Hotel

10/10 Excellent
"Friendly staff. Nice rooms. Good location/value."
William 1-night trip
Posted 1 day ago
New Haven Hotel

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Cheshire Historic District in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $175 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!: This vacation home rental outside of Cheshire Historic District is located near the beach and has a selection of games, a barbecue grill, 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 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.