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Check prices for these dates

Next weekend
14 Rab. I - 16 Rab. I
In two weeks
21 Rab. I - 23 Rab. I
In one month
4 Rab. II - 6 Rab. II
In two months
2 Jum. I - 4 Jum. I

Compare 278 Vacation Homes in Cheshire with updated reviews, rates, and availability.

McAngel Haven: 5 mins from Yale
Fridge, microwave, oven, stovetop

McAngel Haven: 5 mins from Yale

9.8 out of 10, Exceptional, (10)
"Excellent to had a nice house like that "
The price is SAR 956
SAR 2,126 total
includes taxes & fees
4 Mar - 5 Mar
McAngel Haven: 5 mins from Yale
Amazing Lakefront Property
Dining

Amazing Lakefront Property

9.8 out of 10, Exceptional, (24)
"Absolutely beautiful house! Super clean! Superb setting! Very comfortable! Amazing view! Many amenities! Host very responsive and kind! The property manager quickly responded to our needs. My family and friends loved the spectacular experience and would definitely comeback! "
Amazing Lakefront Property
Lake house cozy to relax with a family. 6 bedroom very spacious house.
Terrace/patio

Lake house cozy to relax with a family. 6 bedroom very spacious house.

Lake house cozy to relax with a family. 6 bedroom very spacious house.
NEW-Another Fun Downtown Location 1st floor
Interior

NEW-Another Fun Downtown Location 1st floor

2.0 star property
10.0 out of 10, Exceptional, (10)
"Can’t beat proximity to downtown and other CT locations.Unfortunately we were hit with icy conditions so we could not enjoy all it has to offer. Owner checked in on us and kept driveway safe and clear. We really appreciated his hospitality.The rental was well equipped with everything you need. I LOVED the sunny kitchen to enjoy my morning coffee.We’ll definitely come back when it is warmer!"
NEW-Another Fun Downtown Location 1st floor
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (9)
"My friends and I have stayed twice now at this house and have had the best time both times! It has everything we could need in the house and we can’t wait to be back again!"
The price is SAR 2,250
SAR 3,181 total
includes taxes & fees
4 Mar - 5 Mar
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Bright Milford Beach House w/ Outdoor Shower
Property grounds

Bright Milford Beach House w/ Outdoor Shower

9.6 out of 10, Exceptional, (7)
"We had the best time! It was clean, good location, and the owner was wonderful! We even got to go the beach in December! We would definitely rent this place again!!"
Bright Milford Beach House w/ Outdoor Shower
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
Beach nearby, sun loungers, beach towels

Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

10.0 out of 10, Exceptional, (42)
"This property is beautiful and the house is spacious and well equipped for a wonderful stay. The host was attentive and easy to contact when it was necessary. Such a fantastic choice for a stay in a delightful town. "
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
Near Yale with Game Room
Fridge, microwave, oven, stovetop

Near Yale with Game Room

The price is SAR 2,010
SAR 4,283 total
includes taxes & fees
4 Mar - 5 Mar
Near Yale with Game Room
Family Stays: Middletown, CT
Fridge, microwave, oven, stovetop

Family Stays: Middletown, CT

10.0 out of 10, Exceptional, (2)
"We came to stay at Gilbert’s for a quick ski weekend at Powder Ridge. Gilbert was incredibly gracious and accommodating. He was very easy to communicate with, and really went out of his way to make us feel at home. The location is a little loud at night/early morning, as it is very close to a main road. But the property itself was exactly as described. Clean, comfortable, and very welcoming. "
The price is SAR 364
SAR 687 total
includes taxes & fees
26 Mar - 27 Mar
Family Stays: Middletown, CT
Beautiful 3BR, Rare Find, Clean & Guest Favorite
Fridge, microwave, oven, stovetop

Beautiful 3BR, Rare Find, Clean & Guest Favorite

2.0 star property
10.0 out of 10, Exceptional, (2)
"Nice clean 3 bedroom that was as described. It was a short drive to downtown West Hartford."
The price is SAR 491
SAR 1,117 total
includes taxes & fees
4 Mar - 5 Mar
Beautiful 3BR, Rare Find, Clean & Guest Favorite
Enjoy a taste of New England in Historic Guilford Ct
Beach nearby

Enjoy a taste of New England in Historic Guilford Ct

10.0 out of 10, Exceptional, (9)
"Wonderful property combining original details with modern amenities. Well located near the town green and shops. We would definitely stay here again."
Enjoy a taste of New England in Historic Guilford Ct
Ranch style living at its best with country garden & patio!
Exterior

Ranch style living at its best with country garden & patio!

9.6 out of 10, Exceptional, (8)
"Host worked with me due to larger dog. Very accurate instructions and all amenities were very good. Will stay here again"
Ranch style living at its best with country garden & patio!
Walk to Beaches: Sunny East Haven Home w/ Grill
Beach nearby

Walk to Beaches: Sunny East Haven Home w/ Grill

2.0 star property
10.0 out of 10, Exceptional, (3)
"6 of us stayed here for a music festival. The location, fantastic! Ocean views, check. The bedding, the furniture, kitchen supplies....no amenity was overlooked. Happened to meet owner when were checking in. He was great. Couldn't have been more accomodating. Great great place for a few nights or longer. Wush we were here longer. "
Walk to Beaches: Sunny East Haven Home w/ Grill
Home on the sound
Beach

Home on the sound

8.6 out of 10, Excellent, (7)
"This was a greay stay and the property was really cute and cozy. It is an upstairs portion of a duplex "
Home on the sound
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (25)
"This house is amazing! Has everything we needed for our stay and very clean. Dan was accessible and very responsive at all times. Highly recommend!"
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Interior

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
Blue Back Bungalow
Exterior

Blue Back Bungalow

2.0 star property
9.8 out of 10, Exceptional, (9)
"Thank you so much for the amazing stay!!!! The place is beautiful, very clean and cosy! True Jem of West Hartford! We were here for my nieces wedding and felt very comfortable! Thank you for the wonderful TV set, amazing furniture, blow dryer and decorations! Everything in the house set up well and with love."
The price is SAR 469
SAR 1,462 total
includes taxes & fees
16 Mar - 17 Mar
Blue Back Bungalow
Spacious 18th Century Victorian Mansion - Sleep 16+ Large Group
Interior

Spacious 18th Century Victorian Mansion - Sleep 16+ Large Group

10.0 out of 10, Exceptional, (1)
"We had a lovely family gathering with 14 adults and a toddler - the house was perfect for a large family meal and had room for everyone. Lots of games, a pool table, and electric fireplace were great additions. Rick was very helpful and easy to communicate with. Convenient on site parking. As stated in listing, the bedrooms are on 2nd and 3rd floor, with grand/tall staircases. Overall it was a great place for our family to celebrate together!"
The price is SAR 3,601
SAR 6,352 total
includes taxes & fees
4 Mar - 5 Mar
Spacious 18th Century Victorian Mansion - Sleep 16+ Large Group
Charming Coastal Retreat Steps from the Beach!
Smart TV, fireplace, books, stereo

Charming Coastal Retreat Steps from the Beach!

9.8 out of 10, Exceptional, (32)
"The house was perfect for our multi generation gathering, spacious enough for all. The kitchen was well equipped for our cooking needs. The beds very comfortable. Would highly recommend it!"
Charming Coastal Retreat Steps from the Beach!
Lakeside luxury: beautiful, relaxing 4 bedroom home
Property grounds

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (18)
"We enjoyed the lovely view of the lake and our wonderful, brisk walks in the neighborhood. The spacious and well-appointed lake home was perfect of our family with young adult children. We loved this beautiful, comfortable and entertaining home on the lake and hope to return."
Lakeside luxury: beautiful, relaxing 4 bedroom home
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 property types in Cheshire

New Haven Village Suites
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (2010)
"It was a pleasant stay for my 2 days."
The price is SAR 331
SAR 380 total
includes taxes & fees
10 Mar - 11 Mar
New Haven Village Suites
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, (39)
"I was completely satisfied with my stay. Apartment had wonderful amenities and an amazing view. Great location near downtown restaurants too."
Luxury Furnished Apartments by Hyatus Downtown at Yale
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms
On the beach, beach towels

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

10.0 out of 10, Exceptional, (59)
"Our family ranged in ages from 13 to 96. We were 12 people for a couple days and then 10. We all had a marvelous time and my mom just can’t stop talking about how beautiful the view and the antique furniture was. It was difficult for that many people only having two bathrooms, but we made it work. We did run out of hot water so we learned to scatter showers when possible. The view is amazing and the location was wonderful for us. I can’t say enough, how accommodating our hostess was. We told her...
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms
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.