Thimble Islands vacation rentals

We found 345 vacation rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

Find the perfect vacation rental for your Thimble Islands getaway

Learn about the unique charm of Thimble Islands with a stay in a private vacation home. This city has something for everyone. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Thimble Islands

Do you want to discover attractions to visit while you're in the area? Venture out of your cozy vacation rental and experience everything that makes Thimble Islands a one-of-a-kind vacation spot. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Chamard Vineyards (11.5 mi / 18.5 km)
  • Bishops Orchard and Winery (4.2 mi / 6.7 km)
  • Chatfield Hollow State Park (11.8 mi / 18.9 km)
  • Tradition Golf Club at Wallingford (12.7 mi / 20.5 km)
  • Yale Golf Course (12.9 mi / 20.8 km)
  • Gouveia Winery (13.1 mi / 21 km)

Exploring the natural features in Thimble Islands

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Thimble Islands. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Double Beach (4.1 mi / 6.5 km)
  • East Haven Town Beach (5.9 mi / 9.6 km)
  • Lighthouse Point Park (7.6 mi / 12.2 km)
  • East Rock Park (9.4 mi / 15.1 km)
  • Sandy Point Beach (9.4 mi / 15.2 km)
  • New Haven Green (9.8 mi / 15.8 km)

Frequently asked questions

What is the most popular type of vacation rental accommodation in Thimble Islands?

Houses are the most popular kind of vacation rental in Thimble Islands, according to our data. Even if you've got something a little different in mind, Vrbo has vacation homes in loads of sizes and shapes. Compare our options to find your perfect pad.

How much does it cost to rent a vacation rental in Thimble Islands?

Different factors can influence what you'll pay for a vacation rental in Thimble Islands, including the length of stay, season and type of property. Still, all of our vacation homes have something in common — incredible value. Just enter your travel dates to find your ideal fit.

How much does it cost to rent a beach house in Thimble Islands?

When you travel and the size and style of the property will determine the cost of your beachside stay. Put in your Thimble Islands travel dates to see all your options on Vrbo. Did someone just say "private pool"? Use our filters to pick the features and amenities you need.

Are there pet-friendly vacation rentals in Thimble Islands?

There certainly are. You'll have your pick of two vacation homes that welcome pets in Thimble Islands on Vrbo. Our furry friends deserve a break too, so simply use our search function for pet-friendly vacation rentals to book a perfect pad where your pooch can join in the fun.

What are popular rental amenities in Thimble Islands?

When it comes to rental amenities that people are searching for in Thimble Islands, a beach view, a barbecue grill and a water view rank the highest. With Vrbo vacation rentals, you'll discover options to match your style and taste, whether you're going on a trip with family members, friends or even pets.

Are there large group vacation rentals in Thimble Islands?

With two Thimble Islands properties that can sleep five or more people, you can invite a few extra buddies or family members along. Whether you're planning a casual gathering or a birthday party, we'll help you find the ideal space to match the occasion.

Are there vacation rentals in Thimble Islands that welcome kids?

Gather your entire family for fun-filled adventures in Thimble Islands at one of our two family-friendly vacation rentals. These stays provide conveniences that are ideal for getaways with youngsters, including laundries, extra bedrooms and outdoor spaces. Simply check the "Properties good for families" filter and choose your favorite option.

What are the top attractions for families in Thimble Islands?

Keep the kids entertained at these leading family-friendly attractions in Thimble Islands:

  • East Haven Town Beach
  • Bill Miller’s Castle
  • Lighthouse Point Park

How old do you have to be to rent a vacation rental in Thimble Islands?

The minimum age is normally 16, 18 or 21. It can differ from one property to another on Vrbo, so check the rules of your chosen Thimble Islands vacation home before booking your trip.

How long can I rent a vacation rental in Thimble Islands for?

The amount of time you can book a Thimble Islands vacation home for differs depending on the property. Just enter your dates of travel to view options offering longer term stays. They come with all the things you need to make your extended break more enjoyable like air conditioning and laundries. Some vacation rentals may also offer discounted weekly or monthly prices, so you can stay even longer for less.

More Vacation Rentals ideas

People also search for