Discover a selection of 146 vacation rentals in Thimble Islands, CT that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and kitchens. Prices start at $180 per night, and houses and cabins are popular options for a stay in Thimble Islands. Either way, you'll find a rental for everyone's needs.
Destination guide

Find the perfect vacation rental for your Thimble Islands getaway

Experience the unique character of Thimble Islands with a stay in a vacation home rental. There's no shortage of things to see and do in the area.East Rock Park and Yale Bowl are just a couple of the must-sees in the area. A vacation rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.


Activities and attractions in and around Thimble Islands

Are you hoping to discover attractions to visit in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Thimble Islands a fun spot to vacation. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Bishops Orchard and Winery (4.2 mi / 6.7 km)
  • Connecticut Sportsplex (6.4 mi / 10.2 km)
  • Chamard Vineyards (11.6 mi / 18.6 km)
  • Chatfield Hollow State Park (11.8 mi / 18.9 km)
  • Tradition Golf Club at Wallingford (12.7 mi / 20.5 km)
  • Robert Treat Farm (12.8 mi / 20.5 km)
Natural features

Exploring the natural features in Thimble Islands

Whether you're an active traveler or just want to spend some time taking in the scenery, Thimble Islands is a great place to spend some time outside. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • East Rock Park (10 mi / 16.2 km)
  • Double Beach (4.1 mi / 6.5 km)
  • Chaffinch Island State Park (4.2 mi / 6.8 km)
  • East Haven Town Beach (6 mi / 9.6 km)
  • Lighthouse Point Park (7.7 mi / 12.3 km)
  • Fort Hale Park (7.8 mi / 12.5 km)
How to get there

Transportation options to and around Thimble Islands

Fly into New Haven, CT (HVN-Tweed - New Haven Regional), the closest airport, located 7.2 mi (11.7 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Bridgeport, CT (BDR-Igor I. Sikorsky Memorial), which is 20.5 mi (33 km) away.

How many vacation rentals are available around Thimble Islands, CT?

Our 2020 property listings offer a large selection of 146 vacation rentals around Thimble Islands. From 86 house rentals to 25 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Thimble Islands?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Thimble Islands:

  • Westbrook Center: 67 vacation rentals
  • Madison Center: 39 vacation rentals
  • Momauguin: 22 vacation rentals
  • Downtown: 27 vacation rentals
  • The Hill: 22 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Thimble Islands?

Vrbo offers a large selection of vacation rentals near lovely places in Thimble Islands. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Hammonasset Beach State Park: 813 vacation rentals
  • Knights of Columbus Museum: 279 vacation rentals
  • East Haven Town Beach: 281 vacation rentals
  • Yale University: 276 vacation rentals
  • Bill Miller’s Castle: 396 vacation rentals

But there are many other points of interest around Thimble Islands listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Thimble Islands?

Yes, of course. Vrbo has 86 Houses in Thimble Islands. Our other popular types of vacation rentals in Thimble Islands include:

  • Cabins: 25 rentals available
  • Condos/Apartments: 33 rentals available
  • Cottages: 25 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Thimble Islands?

Yes, you can select your preferred vacation rental with pool among our 12 vacation rentals with pool available in Thimble Islands. Please use our search bar to access the selection of vacation rentals available.