Compare Thimble Islands Vacation Rentals

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Thimble Islands Rentals

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

0.03 mi from city center
At this vacation home, guests have access to an arcade/game room, local meal delivery service, and barbecue grills. Staff members can help with accommodation requests, and provide concierge services. This family-friendly vacation home also has a garden.
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

3.63 mi from city center
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
New Cozy 2BR Stay New Haven Close to Yale

New Cozy 2BR Stay New Haven Close to Yale

2 out of 5
8.95 mi from city center
$223 nightly
The price is $232 total per night
$232 total
Oct 6 - Oct 7
Total with taxes and fees
This apartment features a gym and laundry facilities.
Charming Studio| Near Yale| Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven

9.61 mi from city center
$197 nightly
The price is $197 total per night
$197 total
Oct 6 - Oct 7
Total with taxes and fees
At this apartment, guests have access to features like laundry facilities.
Stunning Apt W/ Parking and Gym | Downtown at Yale

Stunning Apt W/ Parking and Gym | Downtown at Yale

9.89 mi from city center
At this apartment, guests have access to an arcade/game room, laundry facilities, and barbecue grills. Staff members can help with accommodation requests, and provide concierge services. This smoke-free apartment building also has a garden.
Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
240 Congress Avenue, New Haven, CT
9.94 mi from city center
Guests staying at Luxury Furnished Apartments by Hyatus Downtown at Yale enjoy a gym, a rooftop terrace, and free WiFi in public areas. There's free parking if you drive. Dry cleaning/laundry services make packing light an option. Additional amenities include an arcade/game room, express check-out, and a TV in a common area.
Shoreline Oasis

Shoreline Oasis

11.82 mi from city center
$230 nightly
The price is $261 total per night
$261 total
Oct 6 - Oct 7
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has a garden.
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

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

12.31 mi from city center
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

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

13.81 mi from city center
$663 nightly
The price is $750 total per night
$750 total
Nov 3 - Nov 4
Total with taxes and fees
At this cabin, guests have access to an arcade/game room, laundry facilities, and barbecue grills. This family-friendly cabin also has a garden.
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

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

14.1 mi from city center
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

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

2 out of 5
16.12 mi from city center
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Waterfront House with picture-perfect views from all 3 levels.

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

16.27 mi from city center
At this vacation home, guests have access to features like laundry facilities. This beach vacation home also has barbecue grills.
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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 Large Group Rentals

How to Book Vacation Rentals in Thimble Islands



🏠 What is the best price for Thimble Islands vacation rentals?

Thimble Islands vacation rentals range in price, starting at $197 per night.


🏠 What types of vacation rentals in Thimble Islands can I rent?

Orbitz offers a wide range of Thimble Islands rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Thimble Islands condo rentals.


🏠 Is it free to cancel my Thimble Islands vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Thimble Islands vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Thimble Islands. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Thimble Islands?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Thimble Islands apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Thimble Islands?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Thimble Islands package deals will get you even more savings.

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