Holiday houses in Long Pond

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Top-rated holiday rentals in Long Pond

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

A spacious deck extends from the cottage, offering unobstructed views of Buzzards Bay. The serene water reflects a clear blue sky, while a sandy beach and distant island can be seen in the background. A picnic table is positioned nearby on the shore.

Home in Mattapoisett

4.9 out of 5 average rating, 51 reviews

Oceanside Cottage with Private Beach

Escape to our Charming Waterfront Cottage in Mattapoisett, MA! Enjoy private beach access, a picnic table with grill, stunning sunrise views, and the serenity of Buzzards Bay. Perfect for couples or families, this cozy retreat features 2 bedrooms, a fully equipped kitchen, and a relaxing deck overlooking the water. Explore nearby historic sites, local dining, and scenic trails. Whether you're craving adventure or tranquility, this coastal gem is the ideal getaway. Make unforgettable memories!

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Top Guest favourite

An outdoor dining area overlooks the tranquil cove. The table is surrounded by six wicker chairs, set against a backdrop of calm blue water and a clear sky dotted with fluffy white clouds.

Cottage in Portsmouth

4.98 out of 5 average rating, 176 reviews

Waterfront Oasis minutes from Newport w/ hot tub!

Welcome to our charming waterfront Oasis! Located on Blue Bill Cove, our private cottage is steps away from Island Park beach, dining, & local attractions. Stroll down Park Ave to enjoy some ice cream and burgers at Schultzy's or a lobster roll from Flo's Clam Shack (seasonal) while you take in the ocean views. Head to Bristol or Newport, relax at one of the local vineyards and breweries, or enjoy a day on the golf course. Our cottage is also conveniently located near wedding venues & colleges.

FamilyValueHot tub

Top Guest favourite

A stunning sunset paints the sky with vibrant colors reflected in the calm water of Woods Pond. The outdoor deck features seating arrangements, while two fishing poles stand ready for use by the private dock. Trees frame the serene view, adding a natural touch.

Home in Middleborough

5.0 out of 5 average rating, 60 reviews

Pelicans Bog on Woods Pond in Middleboro

Centrally located in Middleboro, this 3 bedroom house on Woods Pond is in a private community. Enjoy the massively spacious out door space while you fish directly off your private dock in the water. Kayak the pond with 2 tandem kayaks provided. Enjoy breezy dinners on the elevated deck overlooking the pond. There is an Air Hockey table located just off the basement bonus room or the foosball table inside. A dedicated large office space fully equipped and minutes to MBTA 1 hour to Boston.

LocationFamilyView

Top Guest favourite

A historic home features classic New England architecture, with a peaked roof and wooden shingle siding. White trim outlines the windows and door, while a white picket fence surrounds the property. Lush greenery and colorful flowers enhance the welcoming exterior under a clear blue sky.

Home in Sandwich

5.0 out of 5 average rating, 247 reviews

Quintessential Waterfront Historic Cottage

Set in a historic district and on a quiet pond shore, create memories with family and friends that will last a lifetime. Enjoy quintessential New England views from every angle. Coffee, restaurants, shopping & a fresh spring water fountain within a short walk to village center and under a mile to the nearest beach. Spend time walking the local area, exploring Cape Cod and relaxing in an atmospheric setting. Each room has been curated in a timeless tone, with relaxation and comfort in mind.

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Superhost

Guesthouse in Freetown

4.91 out of 5 average rating, 11 reviews

The Knotty Witch Waterfront Retreat w Full Kitchen

Escape to the tranquil beauty of the Assonet River with a stay in this charming second-floor getaway. The home features a covered deck that's perfect for enjoying your morning coffee or unwinding in the evening while taking in the stunning views. You'll find a spacious living space and a fully equipped kitchen, providing everything you need for a relaxing getaway. This serene retreat is perfect for business travel, couples or families looking for a peaceful escape. Travel nurse friendly.

LocationValueGetting around

Top Guest favourite

The exterior of the modern houseboat features a wooden façade and large windows. A small patio area includes two wooden chairs with white cushions, positioned on a textured surface beside the water. The setting is bright under a clear blue sky.

Houseboat in New Bedford

4.96 out of 5 average rating, 80 reviews

Drift Loft Houseboat

Stay aboard this charming houseboat with rooftop seating and the best harbor views, overlooking the historic New Bedford-Fairhaven Swing Bridge. Minutes to beaches, ferries to Martha’s Vineyard & Nantucket, downtown dining, and the Whaling Museum. Steps from Fathoms (award-winning chowder!). Walkable, convenient, unforgettable waterfront escape. 4 min drive to Seastreak Ferry 3 min drive to commuter rail 🚉 10 min walk to downtown New Bedford 2 min walk to Dunkin’ and liquor store

FamilyValueOutdoor spaces

Superhost

The exterior of a cozy cabin is displayed, featuring white siding and decorative wooden shutters. A simple stone pathway leads to the front door, surrounded by well-maintained greenery and blooming flowers, all under a clear blue sky.

Cottage in Lakeville

4.68 out of 5 average rating, 95 reviews

Cozy Lake cabin Boston/Providence/Cape Cod

This cozy cabin is located just steps away from beach access to Long Pond, one of Massachusett's largest fully recreational Lakes. Newly renovated kitchen/bath. Beds feature luxurious sleeping accommodations including UGG bedding. The backyard features a seating area/fire pit and grill. Pets welcome Centrally Located!! 45 minutes outside of Boston 25 minutes away from Cape Cod and the ocean. 30 min from Providence Rhode Island 2 hours from the White Mountains of New Hampshire.

FamilyValueNearby

Superhost

A serene lakeside view features calm waters reflecting pastel hues of the sunset. Smooth stone pathways lead to a grassy area, where comfortable seating arrangements are visible. The landscape is framed by trees, adding a natural element to the tranquil outdoor setting.

Home in Lakeville

4.87 out of 5 average rating, 76 reviews

Lakefront Retreat -Private Dock+Kayaks on the Lake

Escape to Long Pond, Massachusetts’ premier fully recreational lake. This beautifully renovated 3-bedroom, 2-bath waterfront retreat features a private dock plus kayaks, canoe, rowboat, and paddleboard for your enjoyment. Swim, boat, jet ski, fish, water ski, tube, or simply relax by the water. Conveniently located within 30-45 minutes of Cape Cod, historic Plymouth, downtown New Bedford, beaches, restaurants, and many of Southeastern Massachusetts’ top attractions.

ValueFamilyCheck-in

Superhost

A lakeside view of a charming home with large windows, surrounded by lush greenery. A stone patio features seating arrangements with a pink umbrella, while the shoreline is visible in the foreground. Calm waters reflect the structure, enhancing its serene atmosphere.

Home in Lakeville

4.77 out of 5 average rating, 39 reviews

Shoreline Dreams

Welcome to your dream vacation getaway! Nestled on the serene shores of Long Pond, this charming lakefront home offers the perfect blend of comfort and natural beauty. Step inside to a spacious, open-concept living area adorned with large picture windows that provide breathtaking views of the sparkling water. Outdoor chairs with firepit offer panoramic views of the lake. The private dock is perfect for swimming, fishing, or launching kayaks and paddleboards.

FamilyValueWalkability

Superhost

A handcrafted tree house is perched among trees, supported by wooden stilts. The structure features a rustic exterior with a metal roof and large windows, surrounded by greenery and vibrant pink flowers in the foreground, creating a serene and natural setting.

Treehouse in Wareham

4.97 out of 5 average rating, 243 reviews

Mink Cove Treehouse

A unique adult adventure awaits in this cozy hand crafted tree house! Nestled 12 feet off the ground amongst the chirping birds, red oaks & breathtaking views of Mink Cove in Buzzards Bay. The tree house is accessible by a suspension bridge that leads you to a partially covered porch where you can enjoy a cup of coffee or sit back & take in the sunset with a glass of wine. Step inside to the living space & snuggle up on the couch for an intimate evening.

LocationValueBeach

Guest favourite

Cabin in Freetown

5.0 out of 5 average rating, 62 reviews

Off-Grid (heated) Forest Cabin

Escape to a private off-grid cabin on 40 acres beside Freetown Forest. Easy to access from the road, heated, fully secluded, and perfect for a quiet retreat. Enjoy rustic simplicity with modern essentials, including WiFi and a 12V power source for charging devices. Hike, relax, or work remotely in peaceful nature. A perfect getaway for solo travelers, couples, writers, and anyone needing a reset.

FamilyLocationComfort

Top Guest favourite

A serene sunset over a calm body of water reflects vibrant orange and soft blue hues. Lush green grass borders the shore, while silhouettes of distant trees frame the scene. A dock is visible on the left, offering a peaceful spot to enjoy the view.

Home in Wareham

4.99 out of 5 average rating, 117 reviews

Sunset Cove Beach

This ocean view cottage is perfect for you and your family to relax, unwind and adore the wonderful scenery it has to offer. This charming cottage is on a quiet dead-end street, suitable for a small family or a couple, seeking to appreciate the neighborhood and beaches without the hassle of cape traffic. Come and enjoy the warm water, beautiful sunrises, breathtaking sunsets, and much more.

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