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

Waterfront Beach House
9.6 out of 10, Exceptional, (39)
"This was perfect for us. We had a family funeral and this was a nice retreat. We would stay again for sure. "
Waterfront Beach House
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (126)
"We stayed here for an anniversary weekend away and found the property and neighborhood to be amazing. We enjoyed the hot tub, pool and firepit and went kayaking in the afternoon. Enjoyed amazing sunsets from the deck; Adam gave us spot-on restaurant recommendations. I don't know if the supply of snacks is standard or an anniversary "special", but all in all this place was a wonderful find. Thank you!!"
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
9.0 out of 10, Wonderful, (85)
"We liked the house which is ideal for a large group. But we were disappointed that the water views shown in the photo gallery did not exist as views from the house directly. "
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Coastal Retreat: Waterfront, Deck, Awesome Views
10.0 out of 10, Exceptional, (13)
"My friends and I had a wonderful getaway vacation at this Northfork house. The water views were stunning, and the house had a good mix of indoor and outdoor areas to relax and hangout. Highly recommend. "
Coastal Retreat: Waterfront, Deck, Awesome Views
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
10.0 out of 10, Exceptional, (46)
"The house was beautiful and a perfect place for our family to be at while visiting our daughter who is a student at Yale. We saw the sunrise over the ocean from our bedroom window. Wish we found this sooner!"
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW
9.4 out of 10, Exceptional, (33)
"Our second stay at the cottage. We spent a long weekend and the weather cooperated. The house is quite quirky, but has a really pleasant feel at home vibe. Beds were very comfortable. Kitchen could use some updates, but was sufficient. (still need a new can opener) The porch overlooking the Sound is magical. Nice neighborhood. If you have one...bring a golf cart! Lots of golf carts about. Host is always pleasant, communicating through Vrbo. We hope to return again. Thank you Khalig Family...
OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW
Amazing Lakefront Property
9.8 out of 10, Exceptional, (23)
"Great views and a good central location for day trips 👌. "
Amazing Lakefront Property
Cozy Modern Home
9.6 out of 10, Exceptional, (29)
"I gave the property listing all five stars because all aspects of the property were as described in the listing. The only suggestion l have for improvement of the property would be for hand railings to be installed on the wall side of the stairs to the 2nd floor, as the stairs are very steep and hard to navigate for an older person. "
Cozy Modern Home
Modern 2BR House w/ Fenced Yard & Wi-Fi
9.6 out of 10, Exceptional, (16)
"We had a blast staying at this property. The attention to detail in the amenities provided was amazing. We travelled with our infant and there was a high chair, pack & play, and baby bath available for us to use, this was perfect so we didn’t have to worry about traveling with these items. Loved the toiletry boxes provided for shampoo, conditioner, laundry pods, dish soap, & more! The location was perfect! Nice short walk to the delicious Walnut Beach Creamery, Walnut Beach Coffee House, and...
Modern 2BR House w/ Fenced Yard & Wi-Fi
NEW! Seaside Beach Haven with a private beach!
10.0 out of 10, Exceptional, (11)
"Good"
NEW! Seaside Beach Haven with a private beach!
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
10.0 out of 10, Exceptional, (2)
"Started with Kristine greeting us as we drove in. Was accommodating to our requests and was very quick to reply to our few messages. Clothes dryer is very small. Short walk to a great park and beach."
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
9.6 out of 10, Exceptional, (11)
"Very nice and clean family was visiting my daughter at the University of New Haven was also very close "
The price is SAR 545
SAR 1,043 total
includes taxes & fees
16 Dec - 17 Dec
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
McAngel Haven: 5 mins from Yale
9.6 out of 10, Exceptional, (5)
"The house was perfect for a family of 4 and a couple! It’s a fairly quiet neighborhood so it was a good place to come back to relax each day. Parking for 2 cars was helpful and the coded entry was very easy. Nice setup and thoughtful features. Angela was very responsive and friendly! Definitely recommend!"
The price is SAR 823
SAR 1,988 total
includes taxes & fees
1 Dec - 2 Dec
McAngel Haven: 5 mins from Yale
Ocean Front Beach House with Private Beach Access - Newly Renovated!
10.0 out of 10, Exceptional, (12)
"We rented this house to celebrate my mother’s 80th birthday. The 6 of us had a great time. The house couldn’t be closer to the water. Beautiful house. Plenty of room for everyone. Get comfortable. Clean. Nice quiet street. Great host. Gave us games, towels, and there were more things in the garage that we didn’t even use. Weather wasn’t the best but we made the most of it. Water is very shallow for a long distance so you can easily walk out and hang around when the tide goes down. Overall...
Ocean Front Beach House with Private Beach Access - Newly Renovated!
Home on the sound
8.6 out of 10, Excellent, (7)
"This was a greay stay and the property was really cute and cozy. It is an upstairs portion of a duplex "
Home on the sound
Cozy 2 bedroom home located minutes from downtown
9.6 out of 10, Exceptional, (23)
"We found this house to be the perfect spot just outside downtown New Haven. We did need a car, but the location was great. We had easy access to main roads, downtown, and there was sufficient local restaurants and stores for stocking the house. The unit was as it appeared and the host was responsive and helpful when needed."
Cozy 2 bedroom home located minutes from downtown
Nature's Paradise: Private Dock & Water Views
10.0 out of 10, Exceptional, (7)
"Everything was great"
Nature's Paradise: Private Dock & Water Views
Guilford home -self check in, off-street parking
9.4 out of 10, Exceptional, (8)
"The property was nice, clean and comfortable. "
Guilford home -self check in, off-street parking
The ARLO - Walk to Brewery and Restaurants
10.0 out of 10, Exceptional, (1)
"Great proximity to restaurants graduation venue, Sacred Heart. We had a great time. The property is clean private, and really really cute."
The ARLO - Walk to Brewery and Restaurants
Near Yale 8 beds Gaming Room
The price is SAR 2,066
SAR 4,126 total
includes taxes & fees
20 Nov - 21 Nov
Near Yale 8 beds Gaming Room
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.
Don't see what you're looking for?
See all available properties in Thimble Islands
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, (1963)
"As always, clean and quiet."
The price is SAR 314
SAR 350 total
includes taxes & fees
26 Nov - 27 Nov
New Haven Village Suites
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
10.0 out of 10, Exceptional, (102)
"We really enjoyed our stay. Beds, linens, towels all super comfortable. Kitchen bright and useful. Bathrooms spotless. 2 minute walk to cute beach. Tons of stuff to do in the area. Great, private backyard well appointed with portable fire pit, grill, furniture. Lots of kid games and books and puzzles in house. Need functional carbon monoxide detector. "
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.