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Compare 351 Vacation Homes in Cheshire with updated reviews, rates, and availability.

🌾Welcoming Tiny Home! Downtown & Beachy☀️

10.0 out of 10, Exceptional, (4)
"Just went for a few days, and decided to stay an extra night! Hostess was wonderful as well, and very helpful! Will definitely be going back!"
🌾Welcoming Tiny Home! Downtown & Beachy☀️

Blue Back Bungalow

2.0 star property
9.6 out of 10, Exceptional, (12)
"The stay was amazing and the host was very responsive, understanding and helpful!"
The price is SAR 469
SAR 1,439 total
includes taxes & fees
5 Jun - 6 Jun
Blue Back Bungalow

New Haven Gem w/ Private Pool, Walk to Beach!

9.6 out of 10, Exceptional, (4)
"I enjoyed my stay and would definitely stay again. The amenities were above and beyond and the home has many upgrades. The area where the home is located is quiet and peaceful."
New Haven Gem w/ Private Pool, Walk to Beach!

Cozy dog friendly updated house in quiet village adjacent to park

10.0 out of 10, Exceptional, (29)
"Stayed for two weeks and really enjoyed the experience. Anthony is a fantastic host with great communication. "
Cozy dog friendly updated house in quiet village adjacent to park

Charming Connecticut Retreat Near Museums & Hiking

8.0 out of 10, Very Good, (3)
"We loved this place. It's an older house but the owner had done a wonderful job with restoration and upkeep. The yard was perfect for our large dog and the kitchen was cozy and inviting. We really enjoyed our stay and would definitely return on another trip to do it all over again."
Charming Connecticut Retreat Near Museums & Hiking

New!Quaint & Convenient Hideaway: Great Location

9.8 out of 10, Exceptional, (10)
"Very comfortable house for our stay to visit with family. It was conveniently located near highway and Glastonbury shopping. Owner was extremely communicative and helpful."
New!Quaint & Convenient Hideaway: Great Location

Grammy's Lake House w/ Private Waterfront Access

9.4 out of 10, Exceptional, (12)
"Enjoyable stay, nice property and great views. The home is aged, but the location is amazing! We had a nice weekend excursion to enjoy New England in October. "
Grammy's Lake House w/ Private Waterfront Access

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (21)
"This property was perfect for our weekend trip to celebrate my nieces family/birthday weekend at Fairfield"
Lakeside luxury: beautiful, relaxing 4 bedroom home

Connecticut Retreat: Steps to Historic Downtown!

9.6 out of 10, Exceptional, (13)
"Everything was as described and updated we enjoyed our stay. "
Connecticut Retreat: Steps to Historic Downtown!

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

9.8 out of 10, Exceptional, (6)
"Loved the feeling of being in a family cottage near the beautiful water and pretty old homes "
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

Peaceful Oasis in Naugatuck - Charming 3-Bedroom Home with serene backyard.

Peaceful Oasis in Naugatuck - Charming 3-Bedroom Home with serene backyard.

Bright Milford Beach House w/ Outdoor Shower

9.2 out of 10, Wonderful, (9)
"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

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

10.0 out of 10, Exceptional, (14)
"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 2,251
SAR 3,200 total
includes taxes & fees
22 Jun - 23 Jun
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

Updated ranch Home 4 minutes from the beach on a quiet end street.

8.8 out of 10, Excellent, (6)
"A nice long weekend beach getaway with family. House had everything we needed, was very clean and neat and everyone had their own space too. Our host was very responsive when I messaged him. Lots of places to shop and eat and the beach is super close! Thank you for a great place to stay for a really nice long weekend with my family. We will be back!"
Updated ranch Home 4 minutes from the beach on a quiet end street.

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

10.0 out of 10, Exceptional, (129)
"Although I went went it is cold the view and location were excellant. I can definately see taking advantage of this place during the summer. The host was responsive and available. "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Charming ,affordable, Private 1-bed & 1 ba , safe park. Quiet neighborhood,

The price is SAR 319
SAR 580 total
includes taxes & fees
11 Jun - 12 Jun
Charming ,affordable, Private 1-bed & 1 ba , safe park. Quiet neighborhood,

Relax by the River | Branford Waterfront Home

Relax by the River | Branford Waterfront Home

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

10.0 out of 10, Exceptional, (1)
"Perfect setting for our family as we celebrated a college graduation locally. Great location. Home has many amenities and you cannot beat lake living! Trying to think about a reason we can return. ;-)"
Lake house cozy to relax with a family. 6 bedroom very spacious house.

The Jewel of The Cove - Historic Coastal Retreat

2.0 star property
10.0 out of 10, Exceptional, (2)
"A group of us stayed there for a work trip and it was the perfect situation for us. The beds were SO comfortable! The decor was vibe! Supplies were plenty. Towels were top quality. The fire pit was so fun to use on our last night in town. Very close to a beach so we could dip our toes in the ocean.There is an airport runway behind the property but the noise wasn’t terrible. "
The price is SAR 1,054
SAR 2,292 total
includes taxes & fees
26 Jun - 27 Jun
The Jewel of The Cove - Historic Coastal Retreat

NEW-Another Fun Downtown Location 1st floor

2.0 star property
9.8 out of 10, Exceptional, (17)
"This was our second stay at this VRBO and hope to stay again on return trips to the area."
NEW-Another Fun Downtown Location 1st floor
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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