Thimble Islands Holiday Rentals

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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, (54)
"Loved the property and we will surely be coming back."
Luxury Furnished Apartments by Hyatus Downtown at Yale

Charming Studio| Near Yale| Downtown New Haven

9.0 out of 10, Wonderful, (4)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
The price is NZ$356
includes taxes & fees
29 Sept - 30 Sept
Charming Studio| Near Yale| Downtown New Haven

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 NZ$455
includes taxes & fees
27 Sept - 28 Sept
Shoreline Oasis

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

10.0 out of 10, Exceptional, (46)
"Amazing property, we loved everything about it, highly recommended, will stay again "
The price is NZ$1,210
includes taxes & fees
6 Oct - 7 Oct
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, (14)
"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!

Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

10.0 out of 10, Exceptional, (7)
"My best friend and I wanted to get out of the city with our pups for a long weekend, and this was absolutely the perfect place to do that! Robert was accommodating, kind, and quick to respond. And the neighborhood/community is adorable, friendly, and low key. Being literally steps from the beach was beyond amazing, and being able to sit on the front patio and get the breeze/view was unmatched! Can’t wait to come back again! "
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

Waterfront House with picture-perfect views from all 3 levels.

9.6 out of 10, Exceptional, (93)
"Took our four grandsons here for a week and it was perfect. Location is great and the house worked perfectly for us. Owners could not be easier to work with "
Waterfront House with picture-perfect views from all 3 levels.

Stunning Apt W/ Parking and Gym | Downtown at Yale

10.0 out of 10, Exceptional, (42)
"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

Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

2.0 star property
10.0 out of 10, Exceptional, (7)
Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (127)
"Fantastic all around!"
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

9.8 out of 10, Exceptional, (109)
"Cute place, very clean"
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

Relaxing summer rental, walking distance to the beach, short ride to the outlets

9.8 out of 10, Exceptional, (48)
"Very pleased with this stay. Perfect for us and the kids. Super cute beach home."
Relaxing summer rental, walking distance to the beach, short ride to the outlets

Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

9.8 out of 10, Exceptional, (68)
"Great family get together where we all were very comfortable. "
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge

10.0 out of 10, Exceptional, (69)
"Beautiful home with every aminity you could dream about. Located in a prefect location. Close to beaches and restaurants. Host was available whenever needed. Overall, a prefect vacation home."
UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (144)
"Perfect location for a get-away! Beautiful location on the water. The cottage was cozy & had everything we needed. Very clean. Lots to do in the area. Host was very nice We had a great time and will absolutely be back! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Cozy Two Bedroom Stay In Downtown New Haven!

The price is NZ$560
includes taxes & fees
28 Sept - 29 Sept
Cozy Two Bedroom Stay In Downtown New Haven!

Chic 1-bedroom apartment with WiFi, fitness room in cool New Haven

The price is NZ$528
includes taxes & fees
28 Sept - 29 Sept
Chic 1-bedroom apartment with WiFi, fitness room in cool New Haven

Large Charming Historic House close to Beaches

9.8 out of 10, Exceptional, (31)
"Great place and location. There was 8 of us and plenty of space and beds!"
Large Charming Historic House close to Beaches

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (30)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is NZ$321
includes taxes & fees
29 Sept - 30 Sept
1-bedroom cottage with Grove Beach 🏖️ access.
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.
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Top Thimble Islands Hotel Reviews

Find out more about Thimble Islands

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 favorite 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 depends 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 NZ$321 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 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.