Holiday Rentals Thimble Islands from €218: Find Short-Term Rentals & Holiday Accommodations

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Top Holiday Rentals in Thimble Islands

Relax on the covered porch with a view of the sea, featuring a comfortable seating area with two chairs.

Relax in comfort with a sofa, throw blanket, and natural light pouring in through the large window.

"Loved the overall stay and experience. The private beach access is a bonus"

includes taxes & fees

12 Aug - 13 Aug

Surrounded by lush greenery, this cabin features a cozy porch with seating and a stone pathway leading to the entrance.

"My wife and I loved our weekend stay at this cabin!"

includes taxes & fees

24 Aug - 25 Aug

Stroll up to this charming colonial-style house, featuring a welcoming front porch with a bench and a beautiful garden.

"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!"

includes taxes & fees

12 Aug - 13 Aug

Walk along the beach on a paved path, bordered by grass and rocky shoreline, with the ocean stretching out to the horizon.

"Close to the shore and the heart of Old Saybrook. The house is very comfortable."

includes taxes & fees

8 Sept - 9 Sept

Kitchen features a central island, oven, and white cabinetry with a patterned backsplash.

"The inside was very clean, the back patio/garden area is cute, but the pool was green by day two. Overall we enjoyed our time here"

Enjoy a refreshing dip in the pool surrounded by a deck and basketball hoop.

"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! "

Enjoy a serene sea view from the large window, accompanied by comfortable seating and a small table.

"It was a very nice stay. Sound of the ocean was calming. We would go back. "

Relax in a spacious room with a pool table, comfortable seating area, and large window offering a view of the outside.

includes taxes & fees

12 Aug - 13 Aug

Enjoy a serene beachside retreat with a balcony overlooking the tranquil ocean.

"Very nice place."

Stunning living area with a spiral staircase, dining table, and modern kitchen.

"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. "

Enjoy the ocean view from this room, featuring a sofa, chair, and small table.

includes taxes & fees

12 Aug - 13 Aug

"Charming little cottage that was just right for our trip to the CT shoreline."

Enjoy a city view from the large window, with a dining table and chairs, a sofa, and a side table.

"Great location, great stay!"

Relax in this serene sunroom with a high ceiling and expansive views of the surrounding landscape.

"Perfect home for a big family gathering!"

Guests can enjoy beach access with a sandy shoreline and ocean views.

"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."

Relax in this stylish living room with a high ceiling, leather sofa, and comfortable armchair.

"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."