Holiday rentals with a kayak in Boston

Lakefront cottage for a fun, relaxing getaway.

Enjoy a cozy stay in a lake front cottage. Located in Essex, on chebacco lake, this 3 bedroom, 1.5 bathroom home has everything you could need. Fully stocked kitchen, comfortable living space with wifi and a large TV, and a comfy couch overlooking the lake. We have a external monitor with a keyboard and mouse to set up a workstation if needed. A large deck and seasonal dock to hang out on. Close to the ocean if you get tired of the lake. It's an excellent home base on Boston's North Shore.

Cozy lakeside retreat

Take it easy at this unique and tranquil getaway a perfect spot to recharge and enjoy all Dudley Pond has to offer.Relax on the deck overlooking the water OR explore on a canoe, kayak, or paddleboard OR walk to TheChat (an old speakeasy) for yummy drinks and food. Centrally located in the Metrowest suburbs close to the Mass turnpike and public transportation to downtown Boston. Close to Babson, Wellesley College, Boston University, Brandeis, Framingham State for graduation or parent weekends.

Garden Apartment for Vacation & Business Travelers

The perfect place to rest, relax or work. Visit universities, Salem or family and friends in the area. This English Basement apartment is located on the Mystic River, 10 minutes from Harvard University in Cambridge and 20 minutes from the City of Boston. Enjoy many local outdoor amenities including the Mystic Lakes, parks, playgrounds, tennis/pickleball/basketball courts and jogging paths, all behind our house. We warmly welcome people from all backgrounds as we value and respect diversity.

Stella Maris, 6 bedroom coastal home, water views

Stella Maris is an inter-coastal sanctuary, located on a private, tree lined street, with ever changing views of Cohasset Harbor & surrounding marsh & waterways. The airy floor plan of this contemporary home is perfect for entertaining family and friends. Gathering on the deck at sunset is a favorite. A short walk to Minot Beach and the lovely Minot neighborhood. Close to charming Scituate & Cohasset Harbors with their great restaurant scenes. 5 minutes to the Commuter rail into Boston.

Ocean View Humarock Beach Cottage

Quintessential Humarock Beach cottage just steps from the ocean. Wake up to sea breezes, enjoy sunset walks along the shoreline, and experience one of the South Shore’s most relaxing coastal escapes. Perfect for both relaxation and adventure, the cottage doubles as a sports haven with a beach volleyball court and includes use of kayaks and paddleboards for exploring the coastline and the river. Spend your days on the sand, in the water, or unwinding on the deck as the ocean breeze rolls in.

Hidden Gem near Boston w/ Private lake access

Waterfront 3BR home 1 mile from commuter rail to Boston. 1 mile from Blue hills ski. 2.2 miles from New England's 1st and only TopGolf. This 3BR, 2.5 BA features an open floor plan w/ view of your private lake from the kitchen and dining rooms. Head downstairs to play pool, ping pong or darts. Or relax by the fire and watch tv (all streaming channels). Warmer months turns into a resort: Fishing, boating, swimming, grill, fire pit, furnished cabanas, hiking the blue hills and much much more.

Cohasset Woodland Cabin

Private cabin tucked on a beautiful 10-acre property just 5 minutes from downtown Cohasset. Surrounded by more than 100 additional acres of woods, fields, and walking trails, the cabin offers a rare blend of seclusion and convenience. The property also neighbors Holly Hill Farm, a charming organic farm open to the community. This is a perfect retreat for guests seeking comfort, simplicity, and connection to nature—while still being close to Cohasset’s shops, restaurants, beaches, and harbor.

Amazing Location! New2 Bed downtown w AC sleeps 4

Dockside - Stunning newly renovated First Floor apartment in the heart of Historic Old Town Marblehead. A stone’s throw from Maddies, The Landing, shopping, and right next to the Driftwood Diner for the best breakfast Steps to the harbour where you can easily access local yacht clubs and a public launch service is available for Harbour tours. Prime parking, AC,classic details and a fresh modern space and amenities will provide you with a very relaxing stay in our beautiful Seaside village

Mugford Manor

This charming one-bedroom apartment is located on the second floor of the Samuel Striker House, built in 1725. Our property is within whistling distance to Old Town Marblehead, rich in colonial and revolutionary history and provides numerous shopping and dining options. Conveniently situated near the MBTA bus stop and only a ten-minute drive from downtown Salem, which features a variety of attractions and amenities. 1 queen bed, 1 queen pull-out couch Ample street parking available.

Scituate Oceanfront | Hot Tub & Steps to Beach

Welcome to The Turner Tide, a peaceful coastal escape in Scituate, MA. Perched along the scenic shoreline, this charming home offers sweeping ocean views, salty breezes, and the soothing sound of waves—perfect for couples, small families, or anyone seeking a classic New England beach getaway. Sand Hills beach- less than a minute walk Scituate Lighthouse - 5 min Scituate Harbor - 5 min Museum Beach - 5 min Peggotty Beach- 8 mins drive Explore Scituate magic with us & Learn More Below!

Ocean Park Retreat

Bright and cheery 1 bedroom ground floor apartment with two+ car parking on quiet street in Marblehead's Ocean Park neighborhood, just steps from the ocean. Full size bed and pull-out full-size sofa in living room, private bathroom with in-floor heating, kitchenette with microwave, dishwasher, sink, double induction cook-top, refrigerator, and toaster oven. Laundry access. Walk to the waterfront, watch the sailboats drift by. Fifteen- minute walk to Historic town center.

Newly renovated, close to Foxboro and Boston

Only 10 miles to Foxboro stadium!Private guest suite surrounded by nature and a large yard featuring a large POOL (closed Sep-May) with beach entry and pool slide. Next to Blue Hills and pond, a nature escape close to Boston! Nature trail right by your door! An additional unit with queen bed is available as well. Queen size bed, bathroom, WIFI, smart TV, kitchenette with microwave, coffee maker, toaster, fridge. Stove in a shared kitchen. Massage chair.