Cheshire Historic District Vacation Rentals

Vacation Rentals in Cheshire Historic District

Property grounds
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (110)
"I stayed at this amazing studio cottage with my girlfriend for 2 nights for her birthday. Our hosts, Liz and Adam were simply amazing. They allowed us an early check in and a late check out. Liz even brought out bicycles for us to use to tour around the neighborhood and ride along the shore line. Because it was my girlfriends birthday (or maybe they just do this), they had Prosecco and Orange Juice plus beer and cheese and other snacks for us when we arrived. The cottage is adorable, perfect...
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Business center
Luxury Furnished Apartments by Hyatus Downtown at Yale
3.5 star property
10.0 out of 10, Exceptional, (18)
"Everything was okay, the apartment was great, enough space for 3 people. During the nighttime no noise, silence, good for well sleeping and so on… 5 points!"
Luxury Furnished Apartments by Hyatus Downtown at Yale
On the beach, beach towels
gorgeous victorian direct ocean front single family six bedroom, ten rooms
10.0 out of 10, Exceptional, (51)
"Wonderful host. Easy communication. Great house."
gorgeous victorian direct ocean front single family six bedroom, ten rooms
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Property grounds
Beautiful 4BR Beach House with Private Beach Access.
10.0 out of 10, Exceptional, (64)
"Small house a short walk from beach that well accommodated our party of five. Clean and comfortable, well laid out and equipped with everything you’d need."
Beautiful 4BR Beach House with Private Beach Access.
4 bedrooms, iron/ironing board, WiFi, bed sheets
Waterfront Cottage in Branford
10.0 out of 10, Exceptional, (80)
"The house is beautiful! Clean and organized. We had everything we needed and the view is incredible. We enjoyed the deck very much. So relaxing. My daughter (the bride) and her friends enjoyed getting ready there in the morning. I can’t say enough good things about this house."
Waterfront Cottage in Branford
Property grounds
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
10.0 out of 10, Exceptional, (19)
"We had such a relaxing, wonderful stay at this lakefront oasis. The lake views from the upstairs living room & the downstairs kitchen and yard were lovely. The number of song birds was delightful to watch and hear. We counted 31 birds in <1 hour! We also saw turtles, fish, and a Bald Eagle."
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Aerial view
Private Island Compound with Large Cottage and Guest House
10.0 out of 10, Exceptional, (18)
"Beautiful property with a really cool history! Loved the water toys and little beach!"
Private Island Compound with Large Cottage and Guest House
Interior
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
10.0 out of 10, Exceptional, (40)
"We were in town to celebrate my son's college graduation, and stayed at this beautiful home about 30 minutes from Quinnipiac University. The house was very clean and the check in process was smooth. Stacie was extremely responsive to our inquiries, despite being on vacation in a different time zone. The sitting room area overlooked the Long Island sound, and the master bedroom and kitchen also had beautiful views. The house was stocked with some board games, and also outdoor games (Spikeball,...
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
1 bedroom, desk, iron/ironing board, internet
Guilford Carriage House at Granite Lodge!
10.0 out of 10, Exceptional, (3)
"Gorgeous cottage, spotless, tastefully decorated, thoughtful personal touches, many windows looking into private woods, comfortable bed with beautiful bedding!"
Guilford Carriage House at Granite Lodge!
4 bedrooms, iron/ironing board, bed sheets
New Haven Oasis: Steps to Yale & Fine Dining
10.0 out of 10, Exceptional, (2)
"Was perfect for my family of 8 for the few days we were in New Haven for my PA graduation. Close to all main dining ! Host was very responsive on all questions I had !"
The price is $298
$631 total
includes taxes & fees
May 28 - May 29
New Haven Oasis: Steps to Yale & Fine Dining
Smart TV, fireplace, offices
Amazing Lakefront Property
10.0 out of 10, Exceptional, (15)
"This was my second go round staying at this property. My family and I enjoyed it the first time. More so the second time with the upgrades. Being familiar with the area was a great help. This time we went in the lake and enjoyed ourselves. We are looking forward to returning back again. Thank you Raymond for letting us stay at your property. Richard and Joanne"
Amazing Lakefront Property
Outdoor pool
Private Home - Pool and Close to CT Shoreline Beaches
10.0 out of 10, Exceptional, (3)
"Our group loved the layout of this property and everything was very clean and tidy. We had plenty of room to spread out and the kitchen was well stocked for us to make our meals! The host is very accommodating and responsive as well! A couple things as a heads up for future bookers: - the room with the single bed and little yellow couch is actually attached to the main bedroom. It’s hard to tell in the listing imo. - the other thing I would be aware of is the neighbors do not want VRBOs in...
Private Home - Pool and Close to CT Shoreline Beaches
Property grounds
The Dream Location for Your Perfect Vacation
9.8 out of 10, Exceptional, (15)
"The cottage has the most wonderful views! We loved our stay!"
The Dream Location for Your Perfect Vacation
Fridge, microwave, oven, stovetop
Amazing Waterfront, Private Sandy Beach 🏖Hot Tub, Gorgeous Sunsets
9.8 out of 10, Exceptional, (55)
"Everything was perfect!! House is amazing for family/friends gathering. Spacious, clean and great views. The home was everything we needed to celebrate the holiday. Thank you to host for communication and special touches throughout the home. Highly recommend"
Amazing Waterfront, Private Sandy Beach 🏖Hot Tub, Gorgeous Sunsets
Interior
2 Fl Loft, East Rock, YALE, SOM, New Haven, @ State St/Bishop St -Anchor Lodging
9.8 out of 10, Exceptional, (59)
"Located close to everything you need and in a quiet location close to the Yale Campus.....one of our favorite places to stay when we are in town!"
The price is $147
$293 total
includes taxes & fees
May 22 - May 23
2 Fl Loft, East Rock, YALE, SOM, New Haven, @ State St/Bishop St -Anchor Lodging
Property grounds
Wooster Square New Haven • 3 Bedrooms • Apizza • Yale • SOM • Downtown
9.8 out of 10, Exceptional, (36)
"nice place in New Haven"
The price is $147
$466 total
includes taxes & fees
Jun 4 - Jun 5
Wooster Square New Haven • 3 Bedrooms • Apizza • Yale • SOM • Downtown
Dining
Fun Downtown Location
9.8 out of 10, Exceptional, (47)
"Host was amazing 5 star all the way ... we walked right down the street and had some pizza everything we needed was just around the corner."
Fun Downtown Location
Property grounds
Direct Waterfront Private Beach Escape
9.8 out of 10, Exceptional, (8)
"We had a beautiful time . Kids didn’t wanted to leave. Amazing views from house , mostly just hung out by the water, watched the birds, and enjoyed the amazing views of the sky. We will be definitely back."
Direct Waterfront Private Beach Escape
Property grounds
Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger
9.6 out of 10, Exceptional, (4)
"Super-clean and the kitchen cabinets and drawers were all labeled-a great convenience. The house is situated in a quiet and tranquil spot, perfect for unwinding and enjoying one’s companions. Not avlocation for people who need entertainment, but want tranquility and nature. Would be great if there could be access to the washer and dryer, especially when folks are in and out of the sweet lake. The owners are extremely king and helpful."
Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger
Fridge, microwave, oven, stovetop
Historic Whitneyville Cottage
9.6 out of 10, Exceptional, (10)
"We have stayed in this little cottage several times now. Convenient location for visiting downtown New Haven. Bed is comfortable - kitchen small but it has what you need. Nice walking neighborhood if you have dogs. We will be back."
Historic Whitneyville Cottage
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See all available properties in Cheshire Historic District
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.

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

Exterior detail
New Haven Hotel
3.5 star property
8.8 out of 10, Excellent, (1233)
"All was great!!"
The price is $149
$171 total
includes taxes & fees
May 26 - May 27
New Haven Hotel
Exterior
Cambria Hotel New Haven University Area
3.0 star property
8.8 out of 10, Excellent, (331)
"The staff was amazing,check-in and check-out was easy. Hotel was clean. The beds were amazing! "
The price is $144
$165 total
includes taxes & fees
May 28 - May 29
Cambria Hotel New Haven University Area
Exterior
Holiday Inn Express Southington, an IHG Hotel
2.5 star property
8.4 out of 10, Very Good, (1004)
"I liked my stay and it was a comfortable hotel. Only thing I didnt like is i havent recieved my refund for the incidental fee at check in"
The price is $128
$147 total
includes taxes & fees
May 19 - May 20
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.

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 $96 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.

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?

Amazing Waterfront, Private Sandy Beach 🏖Hot Tub, Gorgeous Sunsets: This vacation home rental outside of Cheshire Historic District is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a spa tub so you can immerse yourself in your vacation.

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 larger area, you’ll find Toyota Oakdale Theatre and Mount Carmel.

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.

Recent reviews of Cheshire Historic District properties
Expedia verified reviews

Wyndham Southbury

Wyndham Southbury

5/5 Excellent
"👍"
A verified traveler stayed at Wyndham Southbury
Posted 2 days ago
Wyndham Southbury