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 highlights

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)

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.

Where to stay around Thimble Islands?

Our 2019 accommodation listings offer a large selection of 142 holiday lettings near Thimble Islands. From 85 Houses to 21 Condos/Apartments, find the best place to stay with your family and friends to discover Thimble Islands area.

What are the most popular points of interest and landmarks to stay near when travelling to Thimble Islands?

HomeAway offers a large selection of holiday accommodations near great places in Thimble Islands. From HomeAway travellers, the most popular points of interest to stay near are:

  • Maplecroft Plaza Shopping Center: 146 holiday lettings
  • Chatfield Hollow State Park: 430 holiday lettings
  • Bill Miller’s Castle: 371 holiday lettings
  • Shoreline Trolley Museum: 269 holiday lettings
  • Paradise Hills Vineyard: 258 holiday lettings

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

Can I rent Houses in Thimble Islands?

Yes, of course. HomeAway offers 85 Houses in Thimble Islands. Our other popular types of Thimble Islands holiday rentals include:

  • Condos/Apartments: 21 self catering accommodations
  • Cabins: 31 self catering accommodations
  • Cottages: 31 self catering accommodations

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

Can I find a holiday accommodation with pool in Thimble Islands?

Yes, you can select your preferred holiday accommodation with pool among our 9 holiday homes with pool available in Thimble Islands. Please use our search bar to access the selection of holiday rentals available.