Thimble Islands Vacation Rentals

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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, (1848)
"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 CA $128
CA $148 total
includes taxes & fees
Jul 1 - Jul 2
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
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Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
10.0 out of 10, Exceptional, (89)
"Mel and her husband were awesome! Perfect beach home and location was perfect. House was immaculate! I will stay there again. I only needed to use the first floor and did not have to use the stairs. Very close to the beach. Thank you, Mel!"
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
9.8 out of 10, Exceptional, (38)
"Great place. Cozy cottage!"
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
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
Luxury Furnished Apartments by Hyatus Downtown at Yale
3.5 star property
10.0 out of 10, Exceptional, (22)
"This was an amazing property to stay at. Super accommodating when we needed to extend our stay. Very clean and easy to check in and out of. They thought of everything even down to the toothpaste!"
Luxury Furnished Apartments by Hyatus Downtown at Yale
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 CA $617
CA $1,127 total
includes taxes & fees
Jul 14 - Jul 15
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, (22)
"Property exactly as described. What an amazing view and right on the beach. Great communication with host. Answered all our questions very promptly. Would definitely recommend."
The price is CA $1,194
CA $1,897 total
includes taxes & fees
Jul 7 - Jul 8
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
10.0 out of 10, Exceptional, (15)
"Donna, the host, was absolutely wonderful. Very responsive. Cute beach bungalow. Very comfortable. Perfect for the three of us, 2 adults and 19 year old daughter. Would absolutely recommend."
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
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
Waterfront Cottage in Branford
10.0 out of 10, Exceptional, (81)
"Beautiful house in a beautiful location! We hope to return soon!"
Waterfront Cottage in Branford
Shalom Cottage with private beach rights.
9.4 out of 10, Exceptional, (8)
"Has everything you need for 2, for a Summer stay. (The portable heater didn't keep up with the December evenings)."
The price is CA $246
CA $396 total
includes taxes & fees
Jun 20 - Jun 21
Shalom Cottage with private beach rights.
Modern, updated spacious home. 5 min walk to beach. 1 min to Water's Edge Resort
10.0 out of 10, Exceptional, (44)
"Property was perfect. Very nicely updated and had everything we needed for a great beach getaway. Kevin was extremely responsive when we had questions. Would definitely stay again!"
Modern, updated spacious home. 5 min walk to beach. 1 min to Water's Edge Resort
NEW Luxury 1bd apt w/all the amenities @ Yale, Wooster Sq, DT New Haven. Pets ok
9.0 out of 10, Wonderful, (2)
"What a great place! Location, location. Located on edge of Little Italy with great restaurants and bars. Our favorite was Zenellis. Less than 15 minute walk to downtown New Haven with lots of dining options. Take in the Trinity Bar nearby- great fun! Furniture was modest but adequate. Great kitchen."
The price is CA $203
CA $430 total
includes taxes & fees
Jun 23 - Jun 24
NEW Luxury 1bd apt w/all the amenities @ Yale, Wooster Sq, DT New Haven. Pets ok
Beautiful 4BR Beach House with Private Beach Access.
10.0 out of 10, Exceptional, (65)
"Visited family back in CT and this was the perfect place to stay. Kind of like a Tardis, it was bigger on the inside! Thank you!"
Beautiful 4BR Beach House with Private Beach Access.
Direct Beachfront Property On Long Island Sound
10.0 out of 10, Exceptional, (26)
"We had a wonderful time on the beach, in the ocean and just relaxing in the house. There were nice restaurants in the area to try and some fun day trips to take with the kids. We'd go back!"
Direct Beachfront Property On Long Island Sound
The Dream Location for Your Perfect Vacation
9.8 out of 10, Exceptional, (15)
"The cottage has the most wonderful views! We loved our stay!"
The Dream Location for Your Perfect Vacation
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons
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!
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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.

Thimble Islands Vacation Rental Travel Info

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, (1248)
"We are visiting Yale. The location of the hotel is good -- walkable to the campus and business around. The room is clean and renovated."
The price is CA $204
CA $235 total
includes taxes & fees
Jun 23 - Jun 24
New Haven Hotel
Red Roof Inn Milford - New Haven
2.0 star property
7.0 out of 10, Good, (1000)
"Always my little spot to go to when pass through, it’s clean always and the atmosphere is clean!!"
The price is CA $114
CA $131 total
includes taxes & fees
Jun 20 - Jun 21
Red Roof Inn Milford - New Haven
Hilton Garden Inn Shelton
3.0 star property
7.6 out of 10, Good, (1001)
"Was great to find a place at the last minute. property is becoming worn."
The price is CA $150
CA $173 total
includes taxes & fees
Jul 1 - Jul 2
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.

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Thimble Islands vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Thimble Islands vacation rentals we have selected for you start as low as CA $128 per night. Entering your travel dates in the search wizard 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. 

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