Thimble Islands Holiday Rentals

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Holiday Rentals in Thimble Islands

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

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

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

10.0 out of 10, Exceptional, (135)
"Perfect location for a get-away! Beautiful location on the water. The cottage was cozy & had everything we needed. Very clean. Lots to do in the area. Host was very nice We had a great time and will absolutely be back! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Shoreline Oasis

9.0 out of 10, Wonderful, (4)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
The price is NZ$426
includes taxes & fees
4 Aug - 5 Aug
Shoreline Oasis

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

10.0 out of 10, Exceptional, (5)
The price is NZ$1,200
includes taxes & fees
28 July - 29 July
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

adorable ranch in beach community

10.0 out of 10, Exceptional, (45)
"Close to the shore and the heart of Old Saybrook. The house is very comfortable."
The price is NZ$1,068
includes taxes & fees
3 Aug - 4 Aug
adorable ranch in beach community

COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

10.0 out of 10, Exceptional, (37)
"My wife and I loved our weekend stay at this cabin!"
The price is NZ$1,234
includes taxes & fees
1 Aug - 2 Aug
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

Luxury Apartments by Hyatus at Pierpont

4.0 star property
9.4 out of 10, Exceptional, (19)
"Excellent location downtown and close to yale. A lot of complimentary amenities and activities. Very nice size rooms. A nice residential feel for a weeks stay."
Luxury Apartments by Hyatus at Pierpont

Minutes to Walnut Beach, newly renovated 3 bedroom home

10.0 out of 10, Exceptional, (5)
"Very nice place."
Minutes to Walnut Beach, newly renovated 3 bedroom home

Charming Westbrook Cottage, Steps to Private Beach

9.8 out of 10, Exceptional, (6)
"Cozy cottage, good location, nice access to the Sound."
Charming Westbrook Cottage, Steps to Private Beach

42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!

8.6 out of 10, Excellent, (7)
"I rented this place because of the location and convenience to the many things we enjoy about Milford CT. The master bedroom is top-notch as well as the living space downstairs. We hoped to use the outdoor fire place make smores, but due to a medical emergency our trip was cut short. Regardless, we enjoyed our stay at 42 Wood Ave. Thank you, Tiffany, for supplying an awesome rental."
42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!

Cozy 3 bedroom minutes from Yale and the beach

8.0 out of 10, Very good, (1)
"Would recommend. It was quaint second story apartment in an older home. Nicely updated."
Cozy 3 bedroom minutes from Yale and the beach

The Beach Nest-Lux Cottage Steps to the Beach

9.8 out of 10, Exceptional, (6)
"Quick weekend stay as we needed to be in the area for a soccer tournament. The house was super clean and had everything we needed. Would definitely stay again. "
The Beach Nest-Lux Cottage Steps to the Beach

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (27)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is NZ$437
includes taxes & fees
31 July - 1 Aug
1-bedroom cottage with Grove Beach 🏖️ 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.

Waterfront Estate Home - Beach and Shared Pool - East

9.8 out of 10, Exceptional, (43)
"Perfect home for a big family gathering!"
Waterfront Estate Home - Beach and Shared Pool - East

Bright Milford Beach House w/ Outdoor Shower

9.4 out of 10, Exceptional, (11)
"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

Updated kitchen, king+queen beds, AC, walk to beach, 1 min to Waters Edge Resort

10.0 out of 10, Exceptional, (61)
"We really enjoyed our stay at the property. The home was very clean, the beds were comfortable, and the location was convenient for all of our weekend activities."
Updated kitchen, king+queen beds, AC, walk to beach, 1 min to Waters Edge Resort

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

9.6 out of 10, Exceptional, (90)
"It was a very nice stay. Sound of the ocean was calming. We would go back. "
Waterfront House with picture-perfect views from all 3 levels.

Amazing Waterfront Home in Branford Private Beach🏖 Panoramic Water Views+Hot Tub

9.8 out of 10, Exceptional, (65)
"We very much enjoyed our stay and were pleasantly surprised by how great the views were from practically every room in the house. Check-in was very simple and there were many nice touches awaiting us at the property. "
Amazing Waterfront Home in Branford Private Beach🏖 Panoramic Water Views+Hot Tub

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

10.0 out of 10, Exceptional, (16)
"I've stayed here multiple times and it was amazing as always. Great communication, clean, and beautiful! "
The price is NZ$1,446
includes taxes & fees
4 Aug - 5 Aug
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
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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Top Thimble Islands Hotel Reviews