Thimble Islands Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Browse Select Thimble Islands Vacation Homes

OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW
9.4 out of 10, Exceptional, (30)
"Amazing house on the beach with tons of space for fun!!! We loved being right on the water. The kids found crabs and fished with some of the locals. Would definitely rent this place again!!"
OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
10.0 out of 10, Exceptional, (111)
"Had a quick work trip and wish we stayed longer! "
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Milford Oasis: 2BR, Wi-Fi, Near Walnut Beach
9.6 out of 10, Exceptional, (14)
"We loved our little cottage, it was a perfect size for us. The backyard was a great space for our grandkids to run around in, which was fun for them as well. It was close to family so we could easily have them over for the day. The owners were very kid an responded quickly to our questions also. We also met some of the neighbors who were a lot of fun too!"
Milford Oasis: 2BR, Wi-Fi, Near Walnut Beach
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
9.4 out of 10, Exceptional, (10)
"Beautiful condo as advertised, great communication."
The price is CA $206
CA $389 total
includes taxes & fees
Sep 24 - Sep 25
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Cozy Ocean Front Retreat with Private Beach!
10.0 out of 10, Exceptional, (10)
"We enjoyed our stay very much; a nice open floor plan and nice big kitchen area, comfortable couches and chairs. A gorgeous prospect out the Master bedroom. "
Cozy Ocean Front Retreat with Private Beach!
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
9.8 out of 10, Exceptional, (24)
"We booked late in summer and spent 2 nights on beach road when we should have stayed longer. Fantastic location, great neighborhood, clean and comfortable beach house, my wife and I very much enjoyed the house and the shore. Can’t wait to book again!"
The price is CA $787
CA $1,361 total
includes taxes & fees
Oct 13 - Oct 14
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Waterfront Beach House
9.6 out of 10, Exceptional, (35)
"Beautiful home in great location. Worked perfectly for our family. House was in amazing shape, outdoor patio was awesome! As prior reviews have said, make sure you have water shoes, the water for the first 5-10 ft is very rocky. But overall everything was amazing"
Waterfront Beach House
Lovely Westbrook Home w/ Patio - Walk to Beach!
8.8 out of 10, Excellent, (3)
"Beautifully decorated comfortable and clean would definitely rent again"
Lovely Westbrook Home w/ Patio - Walk to Beach!
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
10.0 out of 10, Exceptional, (21)
"The house was in a great location, was well-stocked and clean, and the host was very responsive. Would definitely stay here again and highly recommend. "
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
10.0 out of 10, Exceptional, (45)
"This house is beautiful and has everything you need, including a gorgeous view of the Sound. All communication was swift and easy. My family built some wonderful memories here this week!"
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Cozy Westbrook Vacation Rental - Walk to Beach!
9.8 out of 10, Exceptional, (6)
"We had a great time. It was a very convenient location. The house was well stocked with everyday items you typically forget to bring. We would definitely come back and stay again."
Cozy Westbrook Vacation Rental - Walk to Beach!
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
10.0 out of 10, Exceptional, (5)
"To say that the property was in pristine condition and impeccably designed and decorated would be understatements. Everything was perfect and if we could have stayed in this luxurious home longer, we would have. The property was a perfect launching point for our visit to Powder Ridge for mountain biking and to visit other nearby sites in the beautiful area. The host responded to inquiries without delay and was a pleasure to interact with. We highly recommend without hesitation!"
The price is CA $814
CA $1,157 total
includes taxes & fees
Sep 24 - Sep 25
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
8.0 out of 10, Very good, (1)
"The property overall was amazing. The house was amazing. The amenities described in the listing we perfect. I had a ton of fun there. I wish my stay was longer. The added affect was there was a Hammock and a Blackstone Griddle outback. Plus a firepit. Lovely time to spend with your spouse or have a family event. Downfall was the beds were a bit uncomfortable. I didn't get as much sleep as I would have liked. But the rest of the stay made up for it. "
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Home on the sound
8.8 out of 10, Excellent, (6)
"I really enjoyed staying here and the apartment was really nice. The only complaint I have is that there was a pair of underwear with poop stains in the dryer left. The silverware was also all dirty and sticky and had stains all over them"
Home on the sound
Cozy 2 bedroom home located minutes from downtown
9.6 out of 10, Exceptional, (21)
"This was my second stay here and it went very well, yet again. Alioune really knows how to take care of the guest and responds extremely quick to any questions that are sent. The place is great. Very close to everything you are going to need and has plenty of space. Very adequate number of bed/bathrooms. I can't say enough. I'll be staying here again when I'm traveling to New Haven. 5-stars."
Cozy 2 bedroom home located minutes from downtown
Near Yale 8 beds Gaming Room
The price is CA $746
CA $1,491 total
includes taxes & fees
Sep 30 - Oct 1
Near Yale 8 beds Gaming Room
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (123)
"Our stay was incredible! The property was gorgeous- even with the home owners on property we barely saw them. We had full, private access to the backyard space- beach, pool, hot tub, fire pit, etc- all to ourselves. The property was clean and inviting and we will definitely go back. Everyone was so friendly and the area is picturesque. "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
9.2 out of 10, Wonderful, (80)
"We enjoyed our long weekend stay at the Count House. Its location was perfect ... easy beach access, close to the highway, etc. Everything we needed was supplied for us to enjoy the beach, cook our meals, or play games. There was only one full-size kayak with paddle and the paddle board paddle was broken (but we used it by kneeling on the board!). We would definitely return."
The price is CA $204
CA $585 total
includes taxes & fees
Sep 29 - Sep 30
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
gorgeous victorian direct ocean front single family six bedroom, ten rooms
10.0 out of 10, Exceptional, (56)
"My family and I thoroughly enjoyed our getaway. The home is a perfect mix of modern amenities and antique charms. The outdoor areas are outstanding."
gorgeous victorian direct ocean front single family six bedroom, ten rooms
Modern, updated spacious home. 5 min walk to beach. 1 min to Water's Edge Resort
10.0 out of 10, Exceptional, (50)
"Together with our cousins we had such a lovely weekend stay. The house is beautiful, clean, and exactly as described. It is a short walk to the beach, and the kids enjoyed riding their bikes there. We drove to the bigger town beach one of the days which was also beautiful. Our favorite part was to hang on the covered patio at night time after dinner. Thank you for offering your home to us! Highly recommended. "
Modern, updated spacious home. 5 min walk to beach. 1 min to Water's Edge Resort
Don't see what you're looking for?
See all available properties in Thimble Islands
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.
Save an average of 15% on thousands of hotels when you're signed in

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, (1925)
"Excellent! Best kept secret in New Haven. My room was spacious. Lobby was beautiful and had coffee and breakfast. I would stay again, but you must have a car."
The price is CA $134
CA $154 total
includes taxes & fees
Oct 6 - Oct 7
New Haven Village Suites
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
10.0 out of 10, Exceptional, (97)
"Easy walk to the beach! Beach was great too. House was clean and spacious. "
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
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.