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Cheshire Holiday Rentals

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Holiday Rentals in Cheshire

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 NZ$193
includes taxes & fees
24 Nov - 25 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 NZ$427
includes taxes & fees
26 Nov - 27 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 NZ$195
includes taxes & fees
27 Nov - 28 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

A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

10.0 out of 10, Exceptional, (23)
"This was a great spot to stay with friends, with great separate living areas and a great central living room to gather. The location is minutes from downtown Guilford and was very convenient to do and see everything. I would not recommend bringing small children because there is so much beautiful artwork all around the house, but it’s a beautiful retreat for older kids/teens and adults! "
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

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

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

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.

Beachfront 3-bedroom vacation home just 14 minutes from Yale University

10.0 out of 10, Exceptional, (28)
"Very comfortable home. Perfect for our grown family. We enjoyed the relaxed atmosphere, the beach and water views right outside the back steps. We set up our umbrellas and chairs, had fun using the kyack and paddle board. It was a wonderful and relaxing time together! Looking forward to it again next year."
Beachfront 3-bedroom vacation home just 14 minutes from Yale University

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!

Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!

9.8 out of 10, Exceptional, (24)
"I can not say enough about our stay. Hunter was an amazing host and communication was quick, easy, and made the experience delightful!!! The house is bright and comfy and the view was stunning and relaxing. Every room was perfect from bedroom to living room to kitchen. We wanted for nothing. A quiet getaway to relax was what we were looking for and this was the perfect stay for that. We would love to come back again when we need downtime. This was one of our favorite VRBO rentals ever. Thank...
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!

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

Life is Better at the Beach!

10.0 out of 10, Exceptional, (28)
"When I walked in I immediately noticed how spotless the place was. Every room looked exactly like the pictures that were listed. They had all of the essentials. We didn't need anything except food. The host and the people in the neighborhood were friendly. It was a comfortable and fun stay."
Life is Better at the Beach!

Seaside Escape: Relax by Beautiful Jacob’s Beach

9.2 out of 10, Wonderful, (29)
"Pros: Close to town Nicely appointed. Lots of common space. Nice neighborhood Attached 3 season porch Cons: Yard needs Maintenace; overgrown shrubs and weeds, some make it difficult to see leaving driveway and use sidewalk as well as getting to trash/recycle area ants in kitchen "
Seaside Escape: Relax by Beautiful Jacob’s Beach
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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Other types of properties in Cheshire you may be interested in

Holiday Inn Cheshire - Southington, an IHG Hotel

3.0 star property
8.4 out of 10, Very good, (928)
"No hot water for shower "
The price is NZ$190
includes taxes & fees
16 Dec - 17 Dec
Holiday Inn Cheshire - Southington, an IHG Hotel

Cheshire Welcome Inn

2.5 star property
8.4 out of 10, Very good, (629)
"Very nice for one night "
The price is NZ$182
includes taxes & fees
5 Dec - 6 Dec
Cheshire Welcome Inn

Motel 6 New Haven - Branford, CT

2.0 star property
6.6 out of 10, (1007)
"Thanks "
The price is NZ$138
includes taxes & fees
1 Dec - 2 Dec
Motel 6 New Haven - Branford, CT
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

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Frequently asked questions

Can I find a holiday rental in Cheshire?

Yes, there are holiday rentals in Cheshire close to Drazen Orchards, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Cheshire has a good selection of restaurants. Make sure you have time to check out the waterfalls and shopping during your trip.

What are some of the best holiday rentals that Cheshire has to offer?

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub : This holiday home rental outside of Cheshire 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.

How many holiday rentals are there in Cheshire?

Expedia has 3 holiday rentals for your stay in Cheshire.

What’s there to see and do in Cheshire?

Family-friendly attractions include Barker Character, Comic and Cartoon Museum and Cheshire Hollow Farm, whereas Drazen Orchards and Bartlem Park are a couple of great spots to enjoy the outdoors. While here, Maplecroft Plaza Shopping Center and Roaring Brook Park are other places worth a visit.

What’s a holiday rental in Cheshire like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cheshire. Holiday rentals offer amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for small groups.