Holiday Homes in Thimble Islands

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Thimble Islands and around

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Enjoy a refreshing dip in the pool surrounded by a deck and basketball hoop.

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

10.0 out of 10, Exceptional, (136)
"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
Stroll up to this charming colonial-style house, featuring a welcoming front porch with a bench and a beautiful garden.

Shoreline Oasis

8.8 out of 10, Excellent, (5)
"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 €231
includes taxes & fees
5 Sept - 6 Sept
Shoreline Oasis
Cozy 3 bedroom minutes from Yale and the beach
Kitchen features a central island, oven, and white cabinetry with a patterned backsplash.

Cozy 3 bedroom minutes from Yale and the beach

7.0 out of 10, Good, (2)
"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"
Cozy 3 bedroom minutes from Yale and the beach
Minutes to Walnut Beach, newly renovated 3 bedroom home
Enjoy a serene beachside retreat with a balcony overlooking the tranquil ocean.

Minutes to Walnut Beach, newly renovated 3 bedroom home

10.0 out of 10, Exceptional, (6)
"Very nice place."
Minutes to Walnut Beach, newly renovated 3 bedroom home
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
Guests can enjoy a serene beach experience with calm seas and fine sand.

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

10.0 out of 10, Exceptional, (47)
"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.
The Daydreamer - Walk To Walnut Beach, Restaurant + Shops
Stunning marina views with boats docked, surrounded by beautifully lit buildings.

The Daydreamer - Walk To Walnut Beach, Restaurant + Shops

10.0 out of 10, Exceptional, (11)
"5 Star stay!"
The Daydreamer - Walk To Walnut Beach, Restaurant + Shops
Historic New England home ,Reunions Beach pass
Enjoy cooking and dining in this kitchen with a central island and dining table.

Historic New England home ,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 €585
includes taxes & fees
2 Sept - 3 Sept
Historic New England home ,Reunions Beach pass
Updated ranch Home 4 minutes from the beach on a quiet end street.
Enjoy cooking in this well-equipped kitchen with a microwave, toaster, and oven.

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.
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access
Enjoy the ocean view from this room, featuring a sofa, chair, and small table.

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

10.0 out of 10, Exceptional, (5)
The price is €620
includes taxes & fees
11 Aug - 12 Aug
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access
adorable ranch in beach community
Walk along the beach on a paved path, bordered by grass and rocky shoreline, with the ocean stretching out to the horizon.

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 €572
includes taxes & fees
13 Aug - 14 Aug
adorable ranch in beach community
42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!
Relax in this stylish living room with a high ceiling, leather sofa, and comfortable armchair.

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!
The Beach Nest-Lux Cottage Steps to the Beach
Stunning living area with a spiral staircase, dining table, and modern kitchen.

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
UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge
Pathway leads to serene views of the surrounding landscape.

UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge

10.0 out of 10, Exceptional, (63)
"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 HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge
Gorgeous 4BR Beach House with Private Beach Access.
Guests can enjoy beach access with a sandy shoreline and ocean views.

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.
Large Charming Historic House close to Beaches
Enjoy cooking in this well-equipped kitchen with a central island, water dispenser, and stainless steel refrigerator.

Large Charming Historic House close to Beaches

9.6 out of 10, Exceptional, (28)
"Had a wonderful stay. The house was large enough to allow us all to have our own rooms. Location was perfect and within walking distance of everything. "
Large Charming Historic House close to Beaches
Beach community with private beaches
Enjoy cooking in this well-equipped kitchen with an oven, microwave, and stainless steel dishwasher.

Beach community with private beaches

10.0 out of 10, Exceptional, (11)
"We had a wonderful week staying here with my family. It was family friendly, clear, had everything we needed and was a 10 min walk from beach!"
Beach community with private beaches
Cozy 2 bedroom home located minutes from downtown
Kitchen features a central island, microwave, coffee maker, and dining table with four chairs.

Cozy 2 bedroom home located minutes from downtown

9.6 out of 10, Exceptional, (29)
"Perfect stay for the Yale-Harvard game. "
Cozy 2 bedroom home located minutes from downtown
The Jewel of The Cove - Historic Coastal Retreat
Enjoy a serene beach experience with sailboats on the calm sea and palm trees along the shoreline.

The Jewel of The Cove - Historic Coastal Retreat

2.0 star property
10.0 out of 10, Exceptional, (4)
"loved it so much, beautiful property 100 % would stay again "
The price is €453
includes taxes & fees
17 Aug - 18 Aug
The Jewel of The Cove - Historic Coastal Retreat
Dulce La Donna by the beach
Relax on the beach with comfortable lounge chairs and enjoy the ocean views.

Dulce La Donna by the beach

10.0 out of 10, Exceptional, (1)
"The owner is extremely welcoming and communicates very well. "
Dulce La Donna by the beach
Spacious 4-bedroom house with AC, WiFi in welcoming Guilford
Relax in a spacious living area with a comfortable sofa and dining space for casual meals or entertaining.

Spacious 4-bedroom house with AC, WiFi in welcoming Guilford

10.0 out of 10, Exceptional, (2)
" The house was awesome, had an very good layout, great yard, nice deck and it was the perfect place for our group! Great communication with the owner!"
Spacious 4-bedroom house with AC, WiFi in welcoming Guilford
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

Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

10/10 Excellent
"The Breakfast was good. The bed very comfortable "
Evette 2-night trip
Posted 23 hours ago
Hilton Garden Inn Shelton