Thimble Islands vacation rentals

Why visit Thimble Islands

1. Scenic Boat Tours: Experience the charm of Thimble Islands by taking a boat tour to explore picturesque private islands.
2. Charming Beaches: Relax on beautiful beaches and enjoy family-friendly activities in a welcoming atmosphere.
3. Cultural Experiences: Immerse yourself in local culture through various events and historical sites.
4. Diverse Accommodations: Choose from unique vacation rentals, cozy cottages, or stylish apartments for your stay.
5. Outdoor Adventures: Engage in outdoor activities like hiking and coastal exploration amidst stunning scenery.

Popular types of accommodation around Thimble Islands

Thimble Islands offers a charming selection of vacation rentals, including private homes, apartments, and cozy cottages. Whether you're seeking a unique stay at Shalom Cottage or a waterfront escape, you'll find the perfect spot to unwind. Consider the Milford rental unit for added convenience, or explore top hotels in the area for more options. No matter your choice, Thimble Islands promises a memorable getaway tailored to your needs.

• Houses: These are the top choice for travelers seeking spacious and comfortable accommodations ideal for families or groups.
• Apartments: A popular option for couples and solo travelers, offering the convenience of home-like amenities in a cozy setting.
• Cottages: Charming and often situated near the water, cottages provide a quaint escape for those looking for a peaceful retreat.
• Condos: Modern and well-equipped, condos are perfect for those wanting a blend of comfort and luxury during their stay.
• House Boats: For a unique experience, staying on a houseboat allows you to enjoy the water while having all the comforts of home.**

Top attractions around Thimble Islands

Thimble Islands offers a perfect blend of outdoor adventures, cultural experiences, and stunning scenery for vacationers. Visitors can explore beautiful beaches, historic sites, and nearby state parks. Whether traveling solo or with family, you can enjoy activities such as boat tours to fully appreciate the area's charm and natural beauty. Don't miss the chance to immerse yourself in the local culture and outdoor activities that Thimble Islands has to offer.

1. Yale University: A prestigious Ivy League institution, Yale boasts stunning architecture, rich history, and vibrant culture. Explore the campus, visit museums, and enjoy the diverse events that showcase academic excellence.
2. Stony Creek - Thimble Islands Historic District: A charming historic village with picturesque waterfront views, quaint shops, and local art. Experience the cultural vibes and explore the unique architecture that tells the story of this coastal community.
3. Hammonasset Beach State Park: Connecticut's largest shoreline park, offering beautiful sandy beaches, hiking trails, and picnic areas. Enjoy outdoor adventures, scenic views, and opportunities for wildlife watching in a natural setting.

Things to do recommended for couples

For a romantic getaway in Thimble Islands, enjoy a concert at Woolsey Hall, indulge in exquisite wines at Chamard Vineyards, and savor a delightful meal at Anna Mia's. Each venue offers a unique ambiance, perfect for creating cherished memories together.

Things to do recommended for families

Your family vacation in the Thimble Islands will be filled with fun! Visit the Connecticut Sportsplex for exciting sports activities, enjoy the outdoor vibes at the Lighthouse Point Carousel, and relax in the beautiful East Rock Park, perfect for wellness and family bonding.

Things to do recommended for groups

Group travelers to Thimble Islands can enjoy craft beers at Stony Creek Brewery, catch a performance at the Shubert Theater, or shop at Orchard Hill Plaza Shopping Center for a mix of entertainment and family fun—all within a short drive from the islands.

What do I need to keep in mind when booking a vacation around Thimble Islands

When planning your trip, whether you're traveling with friends, family, pets, or seeking extended stays, it's important to prioritize your preferences in the search process. Here are some helpful Vrbo booking tips to assist you.

• Traveling to Thimble Islands with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group activities. Luckily, you can easily filter for these options and many more on Vrbo.
• Traveling to Thimble Islands with young kids: Traveling with young kids can be demanding. It's important to prioritize their comfort and safety, as well as look for age-appropriate features like a private swimming pool. Additionally, keeping in mind your closeness to family-friendly attractions can enhance your experience.
• Taking your pets with you to Thimble Islands: For many families, a vacation isn’t truly enjoyable without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
• Planning for a long term stay visiting Thimble Islands: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include additional features in your search, such as a parking space, a well-equipped kitchen, or a private pool.

Where to stay around Thimble Islands

Thimble Islands, Connecticut, offers a delightful mix of outdoor adventures, cultural experiences, and stunning scenery. Explore charming private islands and cozy beach cottages along the scenic coast of Branford. Enjoy the friendly atmosphere and family-friendly activities that the surrounding neighborhoods provide. Whether you're seeking a relaxing island getaway or an adventurous coastal exploration, Thimble Islands promises an unforgettable vacation experience for everyone.

• New Haven: Located approximately 10 miles from the Thimble Islands, New Haven is a vibrant city renowned for its rich cultural scene and educational institutions. Visitors can immerse themselves in the historic charm of Yale University, which boasts stunning architecture and art galleries. The city offers a range of activities, from shopping at local boutiques to enjoying family-friendly events. The local landmarks include beautiful beaches along the coastline and event venues that frequently host conferences and cultural exhibitions, making it a great spot for both relaxation and exploration.
• Branford: Just 4 miles away from the Thimble Islands, Branford is a picturesque town that highlights the beauty of outdoor activities and scenic views. Known for its family-oriented atmosphere, Branford features lovely beaches and tranquil lakes perfect for a day of relaxation or recreation. The area is rich in educational opportunities, with local schools offering community programs. Visitors can explore the recreational areas that invite hiking, fishing, and picnicking, making it an ideal destination for families looking to enjoy nature.
• Milford: Situated 16 miles from the Thimble Islands, Milford is a charming city that combines outdoor adventure with family fun. The city is home to beautiful parks and family-friendly beaches that provide the perfect backdrop for a day out. Milford also offers a variety of educational and recreational activities, ensuring that visitors of all ages can find something engaging to do. Enjoy the scenic waterfront or explore local attractions that highlight the area's natural beauty, making Milford a delightful stop on your vacation.

Booking with Vrbo is simple

Are you hoping to save some money on your upcoming trip? One effective strategy is to stay flexible with your travel dates, as prices can vary significantly. Additionally, booking a longer stay often leads to substantial savings. To help you find the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to make your travel experience both affordable and enjoyable!

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll receive OneKeyCash™ on your entire booking. Being the organizer truly has its rewards! Sign up for our One Key rewards program to unlock exclusive member discounts and accumulate OneKeyCash™ on eligible stays. Join us today and begin earning!

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers a user-friendly platform for planning your travels. You can easily create new trips, continue from where you last stopped, or manage your existing plans. The properties you've saved or booked are neatly organized into categories: Potential, Upcoming, or Current Trips. To begin exploring the benefits of Trip Boards, simply visit: https://www.vrbo.com/trips.