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

Vacation Rentals 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, (1966)
"Convenient location, helpful staff, comfortable bed. Thanks!"
The price is CA $138
CA $159 total
includes taxes & fees
Dec 2 - Dec 3
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

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

Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly

9.8 out of 10, Exceptional, (43)
"Amazing property and relaxing weekend! 😄 Host was accommodating and responded promptly. Disappointed with accuracy of listing regarding the spa tub and picture/listing of canoe. Planned a canoe day and was unable due to no canoe on property. Dog loved the yard and enjoyed her stay too! "
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.8 out of 10, Exceptional, (34)
"Great location! Clean building And modern. "
Luxury Furnished Apartments by Hyatus Downtown at Yale

Patchogue River Retreat, 8 minute walk to West Beach

10.0 out of 10, Exceptional, (8)
"My staff and I stayed here for a horse show. It was clean and very comfortable. We wished we had time to actual enjoy the house!!!"
Patchogue River Retreat, 8 minute walk to West Beach

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

9.0 out of 10, Wonderful, (86)
"Very cute ranch in a lovely neighborhood. Good location for access to area sites like Hammonasset Beach, Chamard Vineyard, and the Water's Edge. Not truly a "water's view", but the house had all the amenities needed for a fun stay! "
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

9.8 out of 10, Exceptional, (25)
"We spent the weekend at the shore to celebrater my wife's 70th Birthday. The accommodations were fabulous and everyone enjoyed the home, the view and the location. Thank you to our host Laura."
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

10.0 out of 10, Exceptional, (25)
"The house was clean, and very comfortable. They are well stocked, even with our odd allergies, we were able to find some snacks. It saved us a good amount of town since it was a short visit. "
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME

Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

10.0 out of 10, Exceptional, (58)
"Great"
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

10.0 out of 10, Exceptional, (23)
"This was a great spot to stay with friends, with great separate living areas and a great central living room to gather. The location is minutes from downtown Guilford and was very convenient to do and see everything. I would not recommend bringing small children because there is so much beautiful artwork all around the house, but it’s a beautiful retreat for older kids/teens and adults! "
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

Shalom Cottage with private beach rights.

9.0 out of 10, Wonderful, (17)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is CA $129
CA $248 total
includes taxes & fees
Dec 3 - Dec 4
Shalom Cottage with private beach rights.

Waterfront Cottage in Branford

10.0 out of 10, Exceptional, (87)
"The house was perfect for our annual getaway. We are a group of nine women who have been friends for over 45 years. The large well stocked kitchen with amazing view of the water and fireplace made our Friendsgiving meal memorable! The outdoor hot tub, fire pit, and deck with comfy seating topped off the weekend. Great location, plenty of parking, responsive host. 5/5 stars! "
Waterfront Cottage in Branford

Beautiful 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (69)
"our annual girls (5) trip took us to Branford, CT this year. It was awesome to have a private beach access even though we couldn’t get in the water, but it was great for strolls and shell collecting. Would definitely do better with a second bathroom, but we managed just fine. Overall, it’s a nice little place to stay for a getaway. My only issue is not with the hosts or place, but with one of the fees and the checkout process. However, it does not take away from our stay. "
Beautiful 4BR Beach House with Private Beach Access.

Beachfront 3-bedroom vacation home just 14 minutes from Yale University

10.0 out of 10, Exceptional, (28)
"Very comfortable home. Perfect for our grown family. We enjoyed the relaxed atmosphere, the beach and water views right outside the back steps. We set up our umbrellas and chairs, had fun using the kyack and paddle board. It was a wonderful and relaxing time together! Looking forward to it again next year."
Beachfront 3-bedroom vacation home just 14 minutes from Yale University

The Dream Location for Your Perfect Vacation

9.8 out of 10, Exceptional, (16)
"beautiful quiet spot on the beach, great place to stay."
The Dream Location for Your Perfect Vacation

Updated spacious home, huge kitchen, 5 min walk to beach, 1 min to Water's Edge

10.0 out of 10, Exceptional, (54)
"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 spacious home, huge kitchen, 5 min walk to beach, 1 min to Water's Edge

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

10.0 out of 10, Exceptional, (2)
"We had a fantastic time at this rental on the East end of Long Island. The place was clean, spacious, and perfect for our family getaway. Highly recommend!"
The price is CA $746
CA $1,373 total
includes taxes & fees
Dec 4 - Dec 5
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

New Haven Gem w/ Private Pool, Walk to Beach!

9.6 out of 10, Exceptional, (4)
"In town for college visits we were able to stay and use the home as “base” giving everyone space - inside and out to decompress. Kitchen was great and outdoor space is lovely. Beautiful walk to Lighthouse Point Park!"
New Haven Gem w/ Private Pool, Walk to Beach!
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 types of properties in Thimble Islands you may be interested in

New Haven Hotel

3.5 star property
8.8 out of 10, Excellent, (1398)
"The staff friendly and helpful . Room was comfortable,quiet and clean ."
The price is CA $182
CA $209 total
includes taxes & fees
Dec 20 - Dec 21
New Haven Hotel

Motel 6 New Haven - Branford, CT

2.0 star property
6.6 out of 10, (1076)
"Thanks "
The price is CA $97
CA $113 total
includes taxes & fees
Dec 1 - Dec 2
Motel 6 New Haven - Branford, CT

Hilton Garden Inn Shelton

3.0 star property
7.6 out of 10, Good, (1018)
"It’s your people stupid. That’s the reason I keep coming back. You not only missed that on your list of categories, but you have no idea even as to their very names. That tells me you are a poorly managed company when you don’t know how to value your balance sheet - you missed your biggest asset !!! I’m a billionaire investor. Should I short your stock and start a letter writing campaign that Hilton mistreats its employees. Or perhaps I put your stock if you quickly come to your senses. ...
The price is CA $131
CA $150 total
includes taxes & fees
Dec 22 - Dec 23
Hilton Garden Inn Shelton
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.