Waterfront holiday rentals in Massachusetts

Cider House Cottage

Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

Private & Remote, Enjoy Outdoors, Sleep in Luxury

Bit of a wonderland (57 Acres, 100+ 5-star reviews). A place you won't soon forget. Complimentary firewood, 1/2 hour from Boston, camp but sleep in luxury. This cabin is privately located on a retired Christmas tree farm, about a one-quarter mile off the public road. Listen to the water flow, and watch the sunset over the wetlands. This site is ideally suited for a couple looking for an outdoor experience retiring to the comfort and security of a luxury tiny house. Everything is solar-powered.

Panoramic ocean views 100 ft above Cape Cod Bay

Our 5-bdrm Nantucket style beach house has a new kitchen & open living space, with a new deck, all overlooking the entire shoreline of Cape Cod Bay from a commanding perch atop a 100-foot bluff. Whales and seals can be seen from your deck. Located in a private community with its own rocky beach access about 5 min walk from the house where you can hunt for shells & observe the ocean wildlife. This beach is ideal for kayaking. Plymouth also boasts 4 of top 10 rated public golf courses in MA.

2BR Spacious Yacht - Heat & AC- On Freedom Trail

Escape the hustle and bustle of the city and unwind aboard Carpe Diem II, a yacht with 2 comfy queen staterooms for up to 4 adults. Each stateroom has a private bathroom and shower. Unwind on the aft deck with meals and cocktails as the boats sail by on the harbor, or warm up or cool off inside with central A/C and heat. Located in Charlestown Navy Yard, steps to Freedom Trail, North End, and Downtown. Book now and enjoy the unique charm of living on the water in this historic neighborhood.

The little house on Mirror Pond

Escape to our fully renovated tiny pond house on the serene Mirror Pond. Perfect for up to 4 guests, enjoy swimming, kayaking, or floating on tubes. Unwind by the fire pit, barbecue on the deck, or cozy up by the fireplace (our apologize but it is currently not working) with board games on cooler days. With great WiFi, it’s also ideal for a peaceful work retreat. Whether you're here to relax, or get some work done, this tranquil hideaway offers the perfect blend of adventure and relaxation.

Lakefront Suite Two-Room, Comfy, Tranquil

Located on a lovely small lake, the upstairs suite has a panoramic view from the bedroom, a private spa-like bathroom, cotton linens, a comfy bed, A/C and a living room - it feels like an apartment, but no kitchen. Quietly watch lake nature or boats going by, or choose to swim, kayak, or fish. Enjoy industrial history at Lowell's National Park, take a forest walk nearby, or drive 10 min. to Nashua for its many restaurants, a casino, or tax-free shopping. We are one hour from Boston.

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views

Welcome to our charming 3-bedroom lake cottage in Mendon, MA, where every sunrise paints the sky with breathtaking hues over tranquil waters. Accommodates 6 guests, making it ideal for families or couples seeking serenity. Enjoy lakeside coffee, fishing, kayaking, and evenings by the fire pit. We are pet-friendly, so feel free to bring your dogs along — if you have more than 1 dog, please let us know. Conveniently located near restaurants and attractions. Book now for a magical getaway!

AirbytheStream waterfront, private, clean and cozy

Beautiful private camper with outdoor deck on the water. All the creature comforts but half the price. Very private yet 15 minutes to Northampton or Easthampton. Kitchen sink, 2 burner stove, refrigerator, toilet and shower, one queen bed and twin bunk beds, dinette can also turn into a bed. Pots and pans, silverware and cooking utensils are provided. Camper has power and water as well as heat and air conditioning. There is a Blackstone griddle for outdoor cooking.

Berkshire Treehouse Retreat

Escape, unwind and recharge in this double treehouse. A live tree runs through the interior connecting you directly with nature while in the comfort of home. Built with refurbished, materials and hand curated with care and love. Feel like you’re in the middle of nowhere, yet it’s only minutes to the town of Great Barrington for shopping dining or just a walk around town. Use these dreamy separate spaces for sleeping, writing or drawing in peace. LGBTQ+ owned and operated.

The Writer's Retreat: A Sweetwater Stay

Located on the shore of Tully Pond, The Writers Retreat is a newly designed 325sqft lake side cottage with breathtaking views of Tully Mountain. This 4-season cottage is built with salvaged barn wood; up-cycled maple floors and custom built furniture and lighting. It's the little sister to The Fishing Cottage. You'll find this intimate home has everything you need to relax, write the next Great American Novel, connect with a lover, or just plain chill.

Sunrise on the Water's Edge - Riverside Bungalow

Cozy riverside bungalow celebrates panorama views of the peaceful Connecticut River. Multiple levels of outdoor living space, open-air and screened-in. Just minutes from all major points of interest in the Pioneer Valley - including Six Flags New England, MGM Casino Complex, Big E Fairgrounds, Basketball Hall of Fame, and the Greater Springfield Metro area. Only 20 minutes from Bradley International Airport (BDL) in Windsor Locks.

Charming waterfront home. Patio, AC, Shops, Dining

Discover your dream Rockport getaway! You'll stay nestled on Bearskin Neck, in this cozy harborside condo boasting stunning views, steps from shops, beaches, & galleries. Relax on your private patio overlooking the iconic Motif #1 for your morning coffee or evening happy hour. Book now for a fun getaway, year-round! There is one bedroom upstairs and a pullout sofa downstairs that can sleep 2.