Thimble Islands Vacation Rentals from $264: Search Short-Term Rentals

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Vacation Rentals in Thimble Islands

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

$571 nightly

Jul 7 - Jul 8

Total includes taxes and fees

Beach nearby, sun loungers, beach towels

"We stayed for a week and the house was perfect. Comfortable, so clean, very well stocked, really nice decor and a fantastic location. Host was very helpful and responsive. Highly recommend and we will definitely be back. "

$432 nightly

Jul 6 - Jul 7

Total includes taxes and fees

"We loved our stay!"

$804 nightly

Jul 9 - Jul 10

Total includes taxes and fees

"Everyone had a great time, including our puppy! The location is fabulous and we enjoyed all the amenities inside and outside!"

$1,188 nightly

Jul 18 - Jul 19

Total includes taxes and fees

"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. "

$619 nightly

Jul 9 - Jul 10

Total includes taxes and fees

"So the listing said house number 26 but it's really 25. So we circled the block a few times. Then the key was not in the key safe. Called the owner who apologized profusely. Had to wait a half hour for the key. Not ideal. Otherwise ok. "

$233 nightly

Jul 6 - Jul 7

Total includes taxes and fees

"House was perfect for family get together. Enjoyed walking into town for afternoon shopping and dining."

$615 nightly

Jul 31 - Aug 1

Total includes taxes and fees

"perfect location beautiful house"

$668 nightly

Jul 17 - Jul 18

Total includes taxes and fees

" This joke of a property management and Vrbo double booked the property so when we got there after 6 hours of driving, we couldnt stay there! Both the property management and VRBO did more to try and deflect blame on one another instead of just refunding my money asap. I had to wait a week and a half before vrbo approved the refund because of it! If you stay here, call the property management first so you can make sure you're not getting screwed like we did! "

$242 nightly

Jul 10 - Jul 11

Total includes taxes and fees

1 bedroom, iron/ironing board, WiFi, bed sheets

"The place was perfect for a quick weekend trip back to our hometown."

$260 nightly

Jul 13 - Jul 14

Total includes taxes and fees

"Clean and comfortable, in a quiet area. Prefect for a family gathering"

$314 nightly

Jul 7 - Jul 8

Total includes taxes and fees

$1,212 nightly

Jul 13 - Jul 14

Total includes taxes and fees

$818 nightly

Jul 6 - Jul 7

Total includes taxes and fees

"loved it so much, beautiful property 100 % would stay again "

$581 nightly

Jul 28 - Jul 29

Total includes taxes and fees

$602 nightly

Jul 21 - Jul 22

Total includes taxes and fees

"Amazing location & views. House was pristine & had all amenities. Great park & dog walking path across the street"

$844 nightly

Jul 15 - Jul 16

Total includes taxes and fees

$633 nightly

Jul 9 - Jul 10

Total includes taxes and fees

$1,426 nightly

Jul 12 - Jul 13

Total includes taxes and fees

"This was a 2 month stay for us and was not equipped for longer term stays. Storage is a challenge. On the plus side, the host is responds quickly and helped with any issues we had. The location was great as we needed to be in a specific area."

$306 nightly

Jul 7 - Jul 8

Total includes taxes and fees

"The apartment was beautiful. One highlight for the children was the arcade game in the living room. The view of the water was striking from the living room and bedroom. The neighborhood was very quiet. Shakeema was a great host, easy to contact and she responds quickly. Thank you! I would recommend this VRBO to family and friends."

$492 nightly

Jul 22 - Jul 23

Total includes taxes and fees

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Find out more about Thimble Islands

Everything you need to know about Thimble Islands vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Thimble Islands vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Thimble Islands vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Thimble Islands vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Thimble Islands. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Thimble Islands in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $264 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Thimble Islands rentals

At Expedia, we put the best Thimble Islands vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Thimble Islands rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Thimble Islands vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Thimble Islands. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Thimble Islands properties

5/5 Excellent

" The property was very nice with great customer service.We stayed on a Friday night and we could hear the music from the night club behind the hotel late into the night. Other than that I have no complaints about the property."

A verified traveler stayed at New Haven Hotel

Posted 23 hours ago

Best Western Executive Hotel Of New Haven - West Haven

5/5 Excellent

"Our room keys stopped working every time we left the room. Maybe invest in new room keys. Everyone was very kind and helpful otherwise. The ladies behind the desk were all very sweet and helpful. We enjoyed our stay. "

A verified traveler stayed at Best Western Executive Hotel Of New Haven - West Haven

Posted 4 days ago

5/5 Excellent

Excellent choice for us

"Room was extremely nice, unexpectedly with a well-furnished kitchenette. Good HVAC, overall very quiet room even though next to elevator (#514). Valet service was friendly and prompt. Found a great restaurant (Heirloom) in the neighborhood, which was full of them. Blake lobby had a restaurant of its own, but it seem to close very early."

A verified traveler stayed at The Blake Hotel

Posted 4 days ago

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Thimble Islands Vacation Rentals

Check prices for these dates

Vacation Rentals in Thimble Islands

adorable ranch in beach community

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕

Beach front property steps from Long Island Sound!

The Beach Nest-Lux Cottage Steps to the Beach

Shoreline Oasis

🏡🐕Large Hist. New England home❤🐕Pet❤Reunions😎Beach pass

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

BEST Location-Spacious Luxury Oasis-Free Wine

Once the old Schools house now a newly furnished Apartment

New! Trail-side Haven Retreat! Pet friendly

Gorgeous beachfront house with hot tub

Family Home|Pool|HotTub|Near Lighthouse Point Park

The Jewel of The Cove - Historic Coastal Retreat

Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

Clear LI Sound waterview, Wedding pics, Yale&Beach

Beautiful cozy home w jacuzzi & dock for boat

2 water view new homes with outdoor Spa

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Find out more about Thimble Islands

Recent reviews of Thimble Islands properties

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