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Compare 286 Vacation Homes in Thimble Islands with updated reviews, rates, and availability.

Cozy Ocean Front Retreat with Private Beach!

10.0 out of 10, Exceptional, (16)
"The views from this home are great - really enjoyed sunrises from the master bedroom. A very comfortable home with everything we needed. "
Cozy Ocean Front Retreat with Private Beach!

Cozy Westbrook Vacation Rental - Walk to Beach!

10.0 out of 10, Exceptional, (11)
"Stayed at this house for a weekend after Christmas. It was great! Perfect location and easy to get everywhere! Would love to stay again."
Cozy Westbrook Vacation Rental - Walk to Beach!

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 2,148 total
includes taxes & fees
24 Feb - 25 Feb
McAngel Haven: 5 mins from Yale

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

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

10.0 out of 10, Exceptional, (5)
"Perfect getaway for a group of ladies spending a snowy night catching up away from our spouses and kids. Cozy fireplace, beautiful home, ample space and in a great location. Highly recommend!"
The price is SAR 1,875
SAR 3,531 total
includes taxes & fees
24 Feb - 25 Feb
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

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 3,199 total
includes taxes & fees
23 Feb - 24 Feb
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

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.

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

The price is SAR 2,010
SAR 4,267 total
includes taxes & fees
23 Feb - 24 Feb
Near Yale with Game Room

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!

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

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

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!

10.0 out of 10, Exceptional, (24)
"The house is an architectural gem with plenty of space for the family. We enjoyed the fireplace in the evenings."
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

9.8 out of 10, Exceptional, (26)
"When my hometown sib couldn't host, we rented here and had our family Thanksgiving! It was great!"
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Waterfront House with picture-perfect views from all 3 levels.

9.6 out of 10, Exceptional, (78)
"Hosts were great with easy and quick communication! House was very clean and everything is clearly labeled. "
Waterfront House with picture-perfect views from all 3 levels.

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

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 3,600
SAR 6,317 total
includes taxes & fees
20 Mar - 21 Mar
Spacious 18th Century Victorian Mansion - Sleep 16+ Large Group

Storybook Cottage

10.0 out of 10, Exceptional, (1)
"Very charming property, accurate description per listing. Very clean and overall a great stay."
Storybook Cottage

adorable ranch in beach community

10.0 out of 10, Exceptional, (44)
"Beautiful location, lovely neighbors. House is dated as seen in photos. "
adorable ranch in beach community
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 Thimble Islands

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

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

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (2005)
"Easy fast check in"
The price is SAR 331
SAR 380 total
includes taxes & fees
4 Mar - 5 Mar
New Haven Village Suites

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.8 out of 10, Exceptional, (38)
"Great location. Nice place. Noisy neighbors though"
Luxury Furnished Apartments by Hyatus Downtown at Yale
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.