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Vacation Homes in Cheshire

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

10.0 out of 10, Exceptional, (132)
"My husband and I had a wonderful time at this idyllic cottage on the water in Branford. Great location and hosts. Beautiful community for long walks, restaurants nearby. Highly recommend! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Grammy's Lake House w/ Private Waterfront Access

9.4 out of 10, Exceptional, (13)
"Had a great stay with extended family. House had everything we needed plus a great view of a quiet lake. Was a nice quite place to have a relaxing fun filled weekend."
Grammy's Lake House w/ Private Waterfront Access

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

10.0 out of 10, Exceptional, (45)
"Home was very comfortable and a great location. The views were spectacular. Owner gave us great recommendations for restaurants and nearby attractions. "
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

Bright Milford Beach House w/ Outdoor Shower

9.2 out of 10, Wonderful, (10)
"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

Cozy Lakefront Bungalow w firepit/dock/kayaks

10.0 out of 10, Exceptional, (29)
"This is our second time visiting the area and staying at this beautiful home. It's close to many activities for children and adults, easy to access food and services and a beautiful overall area and home. We truly enjoy visiting!"
Cozy Lakefront Bungalow w firepit/dock/kayaks

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (14)
"My friends and stayed for a night. The house is nice and the owners is very communicative. "
The price is AED 826
AED 1,181 total
includes taxes & fees
23 Jul - 24 Jul
Tranquil Litchfield Connecticut Retreat".

🏡🐕Large Hist. New England home❤🐕Pet❤Reunions😎Beach pass

9.2 out of 10, Wonderful, (88)
"House was perfect for family get together. Enjoyed walking into town for afternoon shopping and dining."
The price is AED 1,455
AED 2,549 total
includes taxes & fees
28 Jul - 29 Jul
🏡🐕Large Hist. New England home❤🐕Pet❤Reunions😎Beach pass

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

8.4 out of 10, Very Good, (7)
"It was everything that I expected. Fabian was very attentive and responsive. I would definitely rent again. "
Updated ranch Home 4 minutes from the beach on a quiet end street.

Cozy 3 bedroom minutes from Yale and the beach

Cozy 3 bedroom minutes from Yale and the beach

Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

10.0 out of 10, Exceptional, (3)
"We had a great time, the house felt very cozy and it was spotless. Our host Robert was very nice and answered all of my concerns. I would definitely recommend this lovely house to anyone.I give it 5 stars."
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

Spacious Woodbury Home w/ Pool + Hot Tub!

8.0 out of 10, Very Good, (2)
"The host was very kind and responsive, which we truly appreciated. However, the house was not properly cleaned. There were a lot of flies inside, the basement had a strong musty smell, and the hot tub water was untreated and had a bad odor, With better cleaning, maintenance, and care for the house the stay could have been much more pleasant."
Spacious Woodbury Home w/ Pool + Hot Tub!

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

10.0 out of 10, Exceptional, (57)
"We had a great time and I would highly recommend for your next stay. Very clean and had everything to make your vacation enjoyable."
The price is AED 955
AED 1,669 total
includes taxes & fees
17 Jul - 18 Jul
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

10.0 out of 10, Exceptional, (3)
"I stayed with my mom and the 2 bedroom 1 bath was perfect for our stay. The house way cozy and in a quiet area. Would absolutely stay again; my mom is already talking about coming back to explore more of the surrounding areas!"
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

Cozy 2 bedroom home located minutes from downtown

9.6 out of 10, Exceptional, (26)
"Perfect stay for the Yale-Harvard game. "
Cozy 2 bedroom home located minutes from downtown

Gorgeous 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (74)
"We loved our stay at this beautiful cottage. The entire experience was very smooth, from pre-check in to getting there and even offers to help with anything we needed in our stayThe cottage is very cozy and well-cared for. The rooms are comfortable and the Internet fast. There is a lot to do in the area, with New Haven nearby and many good restaurants."
Gorgeous 4BR Beach House with Private Beach Access.

Private Apartment in Berlin

2.0 star property
10.0 out of 10, Exceptional, (4)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
The price is AED 536
AED 1,584 total
includes taxes & fees
22 Jul - 23 Jul
Private Apartment in Berlin

The Jewel of The Cove - Historic Coastal Retreat

2.0 star property
10.0 out of 10, Exceptional, (3)
"loved it so much, beautiful property 100 % would stay again "
The price is AED 951
AED 2,111 total
includes taxes & fees
3 Aug - 4 Aug
The Jewel of The Cove - Historic Coastal Retreat

7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

10.0 out of 10, Exceptional, (12)
"The house was as advertised and located in a really quiet neighborhood. The host was easy to work with and responded to me each time I texted her. If the opportunity ever comes up again, we would definitely stay at this property again."
7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook

2.0 star property
10.0 out of 10, Exceptional, (7)
"We met our kids (who live on the east coast) at Natures Nest and really enjoyed our time here. We cooked 2 big meals and the kitchen had everything we needed…even spices & coffee. And Marco left some apples, sweets and wine for us! He was very responsive and helpful anytime we had questions, and gave us great recommendations. Everything was great!"
Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook

Westshore Luxury

7.0 out of 10, Good, (4)
"Check-in time was at 12 noon. House was not clean, was asked to come back 3 hours later. Contact property manager, they said to contact the vacation rental company We chose this place because check-in was supposed to be at 12pm as listed but it was not ready at12 o'clock. That was the reason why we chose that place. Because we had a wedding to be at 4 and we wanted Get dressed at rental property. Was explain this to the property manager? Not only the day of but the day before, reminding her...
The price is AED 1,833
AED 2,481 total
includes taxes & fees
28 Jul - 29 Jul
Westshore Luxury
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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