Holiday houses in Thimble Islands

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

Sunny Daze

This dreamy houseboat rests gently at a family-owned marina, where time seems to slow and nature leans in close. Surrounded by peaceful river views, tall grasses, and birdsong, it’s a floating haven for those seeking calm and creativity. Whether you’re sipping coffee on the deck at sunrise or watching the moon ripple across the water, this riverside retreat invites you to drift, dream, and just be. Enjoy a fire or jump on a paddle board or kayak f or an adventure down the river it has it all!

Water Forest Retreat -Octagon

Water Forest retreat is a very private 122ft.² electrified and heated cedar octagon next to a brook on 56 acres of forest with a pond, waterfall, marsh and hiking trails. Cozy up in this quiet comfortable space while listening to Goldmine brook while you sleep. Fire pit, heated outhouse with composting toilet, outdoor dining area, brook, pond and trail head are just steps away. We also have a TREE HOUSE and HIKER’S HAVEN house by the brook. Please click on our profile picture to read more.

“The Lighthouse” A Beach Cottage by the Sea!

Relax at this unique and tranquil getaway. Long Island Sound to the left, hiking trails to the right. Come kick your feet up at this quiet dead-end road. Enjoy all the modern amenities in this gem of a cottage community. Restaurants and nightlife are just a quick stroll away. Avoid roadside hotels and take a vacation for a night, week, or longer! Check in anytime and at your convenience!No keys to lose or to return! This property provides secure, keyless entry with an August Smart Lock!

Enchanted Cottage on the Marsh, walk to beach

Enjoy an idyllic stay at Enchanted Cottage on the Marsh! Private, quiet one bedroom cottage on Farm River with breathtaking views from deck. Take in the herons, ospreys and other birds among the natural surroundings while relaxing on your very private deck. Or take a stroll to the neighborhood beach, trails or a restaurant. Enjoy daily retreat from everyday life. We want you to have a relaxing stay with us, free from worry. 10 min walk to beach, trails, 10 min drive to Yale University.

Waterfront Cottage With Unforgettable Views

Enjoy Sea Breeze Cottage from sunrise to sunset. Spectacular views from two decks. This cottage has a well-appointed kitchen, dock, patio, flat-screen TV, internet, and 2 bedrooms. Here you'll enjoy bird watching, fall leaf-peeping, swimming, and fishing, and we are dog friendly! Minutes from the Guilford train station, local restaurants, shopping, and the historic town green. Sea Breeze is only 20 minutes from New Haven and the Yale campus. We have it all, even the beach towels!

Stedley Creek

Slip into a slower pace in the seaside village of Stony Creek, where quiet coastal charm meets refined comfort. This private one-bedroom retreat offers a serene, light-filled escape designed for relaxation. Attached to a larger home yet completely separate with its own entrance, the space feels peaceful and intentionally curated — perfect after a day by the shore. Enjoy a tranquil waterfront setting just minutes from I-95, downtown Branford, and a short drive to New Haven.

Historic Hearthstone Cottage

Built in 1800 and thoughtfully renovated in 2024, this two-story guest cottage can be the retreat of your dreams. Surrounded by thousands of acres of nature preserve, short walks to scenic vistas, a raging waterfall and countless hiking trails, few places are as peaceful as Hearthstone. Whether you’re looking for a private oasis or romantic getaway, are a parent sharing the beauty of nature, or an artist looking for inspiration, this historic cottage is for you.

The Connecticut Cottage | Historic Modern Charm

Welcome to The Connecticut Cottage — a beautifully restored 1790s stone cottage blending historic New England charm with modern comfort. Thoughtfully renovated from top to bottom, this one-of-a-kind home offers the perfect mix of cozy escape and central convenience along the Connecticut shoreline. Whether you're planning a laid-back coastal getaway or exploring some of New England’s most iconic destinations, you’re perfectly positioned!!

Private Entire Home • Close to New Haven & Shore

This cozy East Haven home blends old charm with modern comfort. You’ll have the whole place to yourself in a quiet spot, just 7 minutes from the beach and close to Yale, downtown New Haven, and Tweed Airport. Inside, you’ll find 1 bedroom, 1 full bath, and a stocked kitchen, ideal for a couple, solo trip, or work stay. With restaurants, trails, and shoreline spots nearby, it’s an easy place to relax or stay on the go.

Waterfront Bliss Tiny Home

Lakeside Bliss in a Tiny Package Step into a world of relaxation at this cozy tiny house on Pattagansett Lake. In addition to the huge picture window overlooking the beautiful natural lake setting, the tiny house is equipped with a queen bed, full kitchen, high speed Wi-Fi, and unmatched ambiance. Perfect for nature lovers or couples looking for a unique stay by the lake!