Thimble Islands Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Thimble Islands

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Luxury Furnished Apartments by Hyatus Downtown at Yale
3.5 star property
9.6 out of 10, Exceptional, (58)
"Loved our stay here. "
Luxury Furnished Apartments by Hyatus Downtown at Yale
Shoreline Oasis
9.2 out of 10, Wonderful, (7)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
The price is AU$407
includes taxes & fees
19 Oct - 20 Oct
Shoreline Oasis
Charming Studio| Near Yale| Downtown New Haven
8.6 out of 10, Excellent, (7)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
The price is AU$331
includes taxes & fees
20 Oct - 21 Oct
Charming Studio| Near Yale| Downtown New Haven
Stunning Apt W/ Parking and Gym | Downtown at Yale
10.0 out of 10, Exceptional, (45)
"High quality experience, walking distance to all we needed, clean and spacious. Excellent support and communication from the hosts, would stay again."
Stunning Apt W/ Parking and Gym | Downtown at Yale
New Cozy 2BR Stay New Haven Close to Yale
2.0 star property
7.4 out of 10, Good, (3)
"Place was great for family and having a washer and dryer was a big help. Place was super clean and comfortable "
The price is AU$409
includes taxes & fees
15 Oct - 16 Oct
New Cozy 2BR Stay New Haven Close to Yale
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
10.0 out of 10, Exceptional, (33)
"Enjoyed our stay"
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
10.0 out of 10, Exceptional, (128)
"Fantastic all around!"
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Exclusive Weekend Fall Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
9.8 out of 10, Exceptional, (69)
"Great family get together where we all were very comfortable. "
Exclusive Weekend Fall Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
10.0 out of 10, Exceptional, (33)
"Very much enjoyed our stay!"
The price is AU$495
includes taxes & fees
15 Oct - 16 Oct
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
DIRECT WATERFRONT with awesome views and near Yale
10.0 out of 10, Exceptional, (1)
"A quick overnight while exploring New Haven. It was rainy but we enjoyed the views and indoor accommodations. We had enough space for the 5 of us and the host had plenty of items in the kitchen for us to make a nice dinner."
The price is AU$704
includes taxes & fees
21 Oct - 22 Oct
DIRECT WATERFRONT with awesome views and near Yale
Cozy Two Bedroom Stay In Downtown New Haven!
10.0 out of 10, Exceptional, (1)
"Exactly as advertised and had nice personal touches. Very close to attractions and very walkable. "
The price is AU$512
includes taxes & fees
15 Oct - 16 Oct
Cozy Two Bedroom Stay In Downtown New Haven!
1-bedroom cottage with Grove Beach 🏖️ access.
9.4 out of 10, Exceptional, (32)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is AU$281
includes taxes & fees
20 Oct - 21 Oct
1-bedroom cottage with Grove Beach 🏖️ access.
Beach house in Milford, CT
10.0 out of 10, Exceptional, (1)
"Beautiful Home right on the Long Island sound, we had such a great time. Beach was easily accessible, The Host’s were amazing and went above and beyond in accommodating us. Highly recommend!!!"
The price is AU$1,439
includes taxes & fees
15 Oct - 16 Oct
Beach house in Milford, CT
Angelica’s safe haven @ west haven
10.0 out of 10, Exceptional, (5)
"Quiet place with spacious living room perfect for movie nights. Also just a 10-minute drive from the beach and multiple dining options. Host was very accommodating and communicative. Would stay here again."
The price is AU$525
includes taxes & fees
16 Oct - 17 Oct
Angelica’s safe haven @ west haven
Large Charming Historic House close to Beaches
9.8 out of 10, Exceptional, (33)
"Great place and location. There was 8 of us and plenty of space and beds!"
Large Charming Historic House close to Beaches
Waterfront Estate Home - Beach and Shared Pool - East
9.8 out of 10, Exceptional, (46)
"Perfect accommodations for our multi-generational family gathering. Lots of space for our group of 13 to find one’s quiet spot, both in the house and outside. Active neighborhood with walkers and bikers, which gave us motivation to join them! A one mile walk into town to grab coffee and browse the local shops. The access to the kayaks and paddle board made for a perfect beach front vacation; with size options of life jackets and water shoes to choose from!John was a great host while there and...
Waterfront Estate Home - Beach and Shared Pool - East
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
10.0 out of 10, Exceptional, (49)
"Amazing property, we loved everything about it, highly recommended, will stay again "
The price is AU$1,163
includes taxes & fees
10 Nov - 11 Nov
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
9.4 out of 10, Exceptional, (15)
"This Carriage House is exactly as described. Wonderful location and setting, just steps away from Branford Point. Hope to visit again soon! "
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Chic 1-bedroom apartment with WiFi, fitness room in cool New Haven
The price is AU$472
includes taxes & fees
16 Oct - 17 Oct
Chic 1-bedroom apartment with WiFi, fitness room in cool New Haven
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

Top Thimble Islands Hotel Reviews

Find out more about Thimble Islands

Everything you need to know about Thimble Islands holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Thimble Islands holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Thimble Islands holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Thimble Islands holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Thimble Islands holiday rentals we have selected for you start as low as AU$281 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Thimble Islands rentals

At Expedia, we put the best Thimble Islands holiday 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 holiday.

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.