
Holiday rentals in Hammonasset Beach
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Top-rated holiday rentals in Hammonasset Beach
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Charm + location. Walk to beach, town, & harbor.
We are sharing our "happy place". Cozy, family-friendly cottage has everything you need to enjoy a lovely vacation in a quintessential New England town. Ideally located between Guilford's famous green, gorgeous harbor and town beach, easily walk everywhere. High-season/weekend rate reflected in general view--check for actual. Recommended for groups of up to 4 (5 if with kids). Second bedroom (king) is open to living area-we provide a folding screen for door area and curtain for “passthrough”.

Adorable single story cottage-by-the-sea
Adorable, quiet seasonal single story cottage-by-the-sea, in Westbrook, CT. The cottage is located approximately 25 yards from private West Beach. You will love the large front porch and living room with plenty of space for everyone. Updated kitchen with all the amenities. Two bedrooms with closets & drawers. Picnic bench with stainless steel grille & Bonfire Solo Stove outside. Hot & cold outdoor shower to wash off the sand, after a day at the beach. Off road parking on the side of the house.

The Rising Tide Cottage
The Rising Tide Cottage is recently updated and located in a quiet neighborhood on the Connecticut shoreline. Downtown Madison is less than a mile away and home to award-winning restaurants, a movie theater, and many shops. We are 5 houses down from our neighborhood Pent Road Beach and supply complimentary beach chairs, towels and umbrella. Enjoy your morning coffee on the private patio watching the tide rise and fall, overlooking a protected wildlife sanctuary at Hammonassett Beach State Park

Peaceful Riverfront Cottage w/Dock, Walk to Beach
This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

Perfect Cape Beach Cottage in Madison CT!
Come enjoy your perfectly quintessential New England vacation in this beautiful beach cottage in Madison, Conncecticut - modern, luxe, and pull-at-your-heart-strings-endearing, your worries will melt away in this peaceful property. DEEDED BEACH ACCESS TO PRIVATE NEIGHBORHOOD SANDY BEACH - pics of the beach included. Note that bedrooms are located at the top of a (one-story) spiral staircase - if anyone in your party has mobility issues or questions on access, please contact host for inputs.

Handcrafted Timber Frame Cabin Retreat
Escape to the woods and slow things down at this beautifully handcrafted timber frame cabin, tucked away among towering trees and nature’s quiet. Built with exposed beams, natural wood, and timeless craftsmanship, this cabin blends rustic charm with modern comfort—perfect for a romantic getaway, creative retreat, or unplugged weekend escape. Whether you’re looking to reconnect, recharge, or simply enjoy the beauty of the forest, this timber frame cabin offers a warm and memorable escape.

Waterside Beach Retreat
Beautiful New England period home steps from the beach on the Long Island Sound. Recently renovated from top to bottom with new kitchen and bathrooms, hardwood floors throughout. Idyllic location on quaint & quiet street. Hide away and relax or discover the many local attractions - water sports, fishing, winery, antique stores, scenic walks, premium outlet shopping are all on your doorstep. Ideally located off the I-95 halfway between NYC & Boston, both of which are a train ride away.

Beach Sanctuary on the Long Island Sound
Kick back and relax in this stylish, retro, newly renovated coastal oasis with beach access & stunning views of the Long Island Sound. You can enjoy bird watching in the backyard garden in the spring, swimming and fishing at the private association beach in the summer, and leaf-peeping in the fall. The Beach Sanctuary is located in charming, historic Guilford CT, minutes from the town green, train station, local restaurants, and shopping as well as 20 minutes from New Haven and Yale.

Historic Coastal Home • Marsh Views • Pet-Friendly
Historic Coastal Home • Marsh Views • Pet-Friendly ★☆ ABOUT THIS SPACE ☆★ Step into a home that blends historic charm with modern comfort, all set against peaceful marsh views—ideally located in the desirable Liberty Green neighborhood. With 4 bedrooms, 3.5 bathrooms, and thoughtful details throughout, you’ll have the perfect retreat for relaxing, working remotely, or exploring the coast. Pet-friendly, cozy, and full of character—this is where your memorable getaway begins.

The Barn by the Sound
Spend a weekend in The Barn: a modern designed free-standing building with guest studio apartment above, designed to look like a barn; the studio has views at tree level of a quiet, old neighborhood; one block from Long Island Sound; on a section of the historic old Boston Post Road. There is lots of natural light coming from a large window with a lovely view of a privet hedge on our property overlooking a park like property across the street.

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!!

Bliss by the Sea - Cozy Beachside Escape
Nestled in the Harborview Beach Association community. This charming single-level home, perfect for up to four guests, features two cozy bedrooms, a full bathroom, and a spacious back deck with a fenced-in yard. Enjoy the convenience of a well-equipped kitchen, entertainment options, and thoughtful amenities, all just a short walk or bike ride from the beach. Relax, unwind, and feel at home from the moment you arrive.
Popular amenities for Hammonasset Beach holiday rentals
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Destinations to explore
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- Yale University
- Mohegan Sun
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Fairfield Beach
- Charlestown Beach
- Ocean Beach Park
- Mystic Seaport Museum
- Southampton Beach
- Mystic Aquarium
- Sunken Meadow State Park
- University of Connecticut
- Hammonasset Beach State Park
- Compo Beach
- Powder Ridge Mountain Park & Resort
- Sleeping Giant State Park
- Yale University Art Gallery
- Wölffer Estate Vineyard
- Ski Sundown
- Long Island Aquarium
- Sherwood Island State Park
- Ocean Beach
- Soundview Beach
- Meschutt Beach





