Search Vacation Homes in Thimble Islands

    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

Compare 294 Vacation Homes in Thimble Islands with updated reviews, rates, and availability.

Cozy Ocean Front Retreat with Private Beach!
10.0 out of 10, Exceptional, (3)
"Had a fabulous weekend at this beach cottage. Great location, extremely close to the water, coffee shop, ice cream shop, lobster rolls, boardwalk along the water and of course the beach! Milford is a hidden gem for summer vacation and I will definitely go back and stay in this beach home!!"
Cozy Ocean Front Retreat with Private Beach!
Ocean Front Beach House with Private Beach Access - Newly Renovated!
10.0 out of 10, Exceptional, (5)
"Great home, great location! Very clean and was perfect for a large family. Host was responsive. Need to fix child door locks on sliders if you're going with children, the tide gets high on the wall."
Ocean Front Beach House with Private Beach Access - Newly Renovated!
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (113)
"Was looking for a coastal retreat to enjoy a couple days with my daughter who lives near this location. This property had everything from a super clean, cozy studio with fridge and counters filled with surprising treats, incredible hot tub with lights in the trees, pool to cool off and little private beach to launch a paddlleboard and kayak, or hang out at night with a burn pit. If you are just a beach person and want toes in the sand and to swim in the ocean, this area is not for you....
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Save an average of 15% on thousands of hotels when you're signed in
Patchogue River Retreat, 8 minute walk to West Beach
10.0 out of 10, Exceptional, (6)
"House was very nice. Location is great. Easy walk to beach and convenient to Westbrook center."
Patchogue River Retreat, 8 minute walk to West Beach
Walkable New Haven Retreat w/ Ocean Views!
9.6 out of 10, Exceptional, (10)
"What a wonderful property! The home was simply beautiful and the view of the water was amazing. We had everything we needed and the home was spotless. There was such attention to detail. We would definitely stay here again. It was a most enjoyable experience. It was the nicest VRBO we have stayed in. Definitely a 5 star rating!"
Walkable New Haven Retreat w/ Ocean Views!
Lovely Westbrook Home w/ Patio - Walk to Beach!
10.0 out of 10, Exceptional, (1)
"Beautifully decorated comfortable and clean would definitely rent again"
Lovely Westbrook Home w/ Patio - Walk to Beach!
Quiet Connecticut Retreat w/ Pool, Deck & Fire Pit
Quiet Connecticut Retreat w/ Pool, Deck & Fire Pit
Updated ranch Home 4 minutes from the beach on a quiet end street.
8.0 out of 10, Very Good, (2)
"Family of 5 (2 adults, 3 teens) stayed for long weekend. Friendly and fairly quick communication with Fabian was appreciated. House is approx 1 to 1.5 miles to Long Island Sound and beach. Nice and quiet neighborhood. The place was clean with exception of downstairs which had some of the owner's personal belongings strewn about. The biggest disappoint was no hot water or heat for most of the stay. Fabian offered hot showers at another nearby location and brought in a space heater which was...
Updated ranch Home 4 minutes from the beach on a quiet end street.
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
10.0 out of 10, Exceptional, (2)
"Quality property with a top notch owner."
The price is SAR 2,251
SAR 3,200 total
includes taxes & fees
26 Jun - 27 Jun
26 Jum. II - 27 Jum. II
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
2BR Home with Fenced Backyard near Walnut Beach
9.6 out of 10, Exceptional, (11)
"I stayed for 4 nights while traveling for business. The location was ideal and I enjoyed being able to walk the beach boardwalk every night. The house had everything I needed, was clean and the host was very responsive. I would stay here again."
2BR Home with Fenced Backyard near Walnut Beach
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
9.0 out of 10, Wonderful, (69)
"We very much enjoyed our stay and the host had everything prepared for us. The check in/out process was very easy as well!"
The price is SAR 1,688
SAR 3,081 total
includes taxes & fees
14 Jul - 15 Jul
14 Raj. - 15 Raj.
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, (51)
"Wonderful host. Easy communication. Great house."
gorgeous victorian direct ocean front single family six bedroom, ten rooms
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
10.0 out of 10, Exceptional, (16)
"My month-long stay was absolutely wonderful. Hunter was an amazing, proactive host. The weather wasn't cooperative in the beginning of my stay, but Hunter went above and beyond to make sure whatever issues arose were taken care of and I couldn't be happier to have made this choice. I will definitely be back!"
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
Cozy Westbrook Vacation Rental - Walk to Beach!
10.0 out of 10, Exceptional, (3)
"Everything one would need for a beach vacation. Responsive contact person."
Cozy Westbrook Vacation Rental - Walk to Beach!
Amazing Lakefront Property
10.0 out of 10, Exceptional, (15)
"This was my second go round staying at this property. My family and I enjoyed it the first time. More so the second time with the upgrades. Being familiar with the area was a great help. This time we went in the lake and enjoyed ourselves. We are looking forward to returning back again. Thank you Raymond for letting us stay at your property. Richard and Joanne"
Amazing Lakefront Property
Direct Waterfront Private Beach Escape
9.8 out of 10, Exceptional, (10)
"Great little spot for a family! Private beach, quiet, everything you need for a beach getaway. Close to places to walk espeically with little ones! We will be back for sure!"
Direct Waterfront Private Beach Escape
Cozy Modern Home
9.6 out of 10, Exceptional, (26)
"Very nice place, stay there for a couple of nights for a get together, plenty of room. Only problem was some of the cleaning supplies where locked away where we couldn’t access it so we had to bring a mop and other supplies."
Cozy Modern Home
Coastal Retreat: Waterfront, Deck, Awesome Views
10.0 out of 10, Exceptional, (8)
"We had an amazing time at this house! My family all came back to Long Island to attend my fathers memorial service nearby and this house had all the details and comforts to make the weekend as enjoyable as possible...and the view is AMAZING! I would definitely recommend this location and would stay there again!"
Coastal Retreat: Waterfront, Deck, Awesome Views
McAngel Haven: 5 mins from Yale
9.0 out of 10, Wonderful, (2)
"The location was good for our needs and the place well maintained. There were scent devices in many outlets and two of our guests are allergic. We had to unplug them and air out the home. It would be good to alert guests to those devices and allow them to choose to have them not present."
McAngel Haven: 5 mins from Yale
PREMIER BEACH HOUSE ~ Steps From The Beach And Restaurants
9.8 out of 10, Exceptional, (22)
"My wife and I recently stayed at this property in Milford, CT and it was wonderful. The home was cozy and the area quiet, letting us have a nice relaxing weekend away from the hustle and bustle of NYC. The space was clean and comfortable with multiple places for sitting and relaxing after a long day out in the sun! Would definitely recommend."
PREMIER BEACH HOUSE ~ Steps From The Beach And Restaurants
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.

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, (1847)
"We stayed only one night as planned. The property is in need of renovation, more than just paint. Our room had a musty smell and the carpets were worn out. The people working there were great. I hope they can rejuvenate this area. "
The price is SAR 351
SAR 390 total
includes taxes & fees
30 Jun - 1 Jul
30 Jum. II - 1 Raj.
New Haven Village Suites
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (113)
"Was looking for a coastal retreat to enjoy a couple days with my daughter who lives near this location. This property had everything from a super clean, cozy studio with fridge and counters filled with surprising treats, incredible hot tub with lights in the trees, pool to cool off and little private beach to launch a paddlleboard and kayak, or hang out at night with a burn pit. If you are just a beach person and want toes in the sand and to swim in the ocean, this area is not for you....
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
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.

Recent reviews of Thimble Islands hotels
Expedia verified reviews