Watch Hill Vacation Rentals
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Our top choices for Watch Hill vacation rentals
Aparthotel in Montauk
Montauk Manor9.2 out of 10, Wonderful, (1271)
"The room was very clean, comfortable and quiet.
The hotel was decorated beautifully for the holidays.
The pool area with hot tub was clean and enjoyable "
Kathleen
The price is ￥21,613
￥27,744 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Cottage in Oakdale,
The Tiny Cottage at Clem & Clyde's10.0 out of 10, Exceptional, (2)
"Cottage was perfect! The fresh eggs given to us by the host made for an awesome breakfast! The host was great! My 2 energetic boys loved every animal. The host made sure to take my boys through every fence/gate there was to get my boys front and center with the animals. This isn’t just about money him seeing my boys smile and run around with the animals definitely made his day! Left about an hour ago and my boys already asked 17 times when we are going back! "
jeff
The price is ￥14,814
￥20,155 total
includes taxes & fees
Dec 28 - Dec 29
Apartment in Stonington
Stevedore Landing-#3 · walk downtown Mystic · train · aquarium10.0 out of 10, Exceptional, (4)
"We enjoyed our stay. The apartment is in excellent condition."
Marcell
The price is ￥11,858
￥33,153 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Apartment in Groton
Escape to the Thames: Quaint Groton Retreat10.0 out of 10, Exceptional, (1)
"The house was neat, well maintained, and very warmly furnished. The host has put some work into the details that make the stay really enjoyable. I would definitely go back. "
Stephen S.
The price is ￥10,604
￥18,900 total
includes taxes & fees
Dec 27 - Dec 28
Cottage in Ledyard
Lakeside cottage ON the water with beautiful views up the lake!9.8 out of 10, Exceptional, (192)
"There were stunning views, it was very relaxing, and we had excellent communication with the host. We couldn’t be happier, it was perfect! Kayaking was the best part. Plenty to see and do in the area as well."
Heather S.
The price is ￥21,676
￥47,695 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Apartment in Old Mystic
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC10.0 out of 10, Exceptional, (27)
"Everything was perfect! Great location, easy check in/out, great amenities in room, and super comfy bed. "
Paul S.
The price is ￥13,894
￥30,910 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Mobile Home in East Lyme
Cozy Lakefront Tiny House10.0 out of 10, Exceptional, (2)
"The bed and pillows were very comfortable. The outside space was very relaxing. Kevin’s place was perfect! We had questions and he replied back right away. We definitely want to go back. "
Rebecca K.
The price is ￥15,971
￥35,111 total
includes taxes & fees
Jan 21 - Jan 22, 2026
Vacation Home in Waterford
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks10.0 out of 10, Exceptional, (11)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
Elaine A.
The price is ￥14,671
￥56,218 total
includes taxes & fees
Jan 5 - Jan 6, 2026
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.
Top Watch Hill Hotel Reviews
Spark by Hilton Mystic Groton
10/10 Excellent
Find out more about Watch Hill
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