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.

River Retreat - Close to Boston

Enjoy a relaxing family getaway at this peaceful home, conveniently located near Boston and the North Shore. This house with amazing deck space is 6 miles from Salem and 6 miles from Boston Logan Airport. You'll be close to the beautiful beaches of the North Shore and only 32 miles from New Hampshire. This property is a 2-minute walk to the Northern Strand Trail, which spans over ten miles from Everett to Lynn. Public transportation is easily accessible, bus stop and Wonderland are very close.

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.

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 and a queen pull-out couch Ample street parking available.

Sunset LAKE VIEW studio. Recently upgraded!

Welcome to Sunset Lake! Enjoy beautiful sunsets year round! Cozy in the winter with plenty of extra blankets and a great heating system! Light a fire at night. We are walking distance to South Braintree Square. You will enjoy nature and still have close proximity to city. Walk to a super market, pharmacy, nail salon, bank, a tavern w/ live music. Other restaurants within walking distance include Mexican, Thai, Sushi, Italian, Vietnamese (pho), pizza and a great local coffee shop ☀️ 🌅

Soak in the Hot Tub! Water Views and Ocean Scent!

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!

2bed Condo in Cambridge w/balcony Garage Parking

2BR Apartment w Balcony in the Heart of Cambridge Welcome to your stylish home away from home! This modern 2-bedroom apartment is located in one of Cambridge's most desirable neighborhoods - just steps from the Charles River, MIT and Kendall Square, and easy access to downtown Boston. • Two beautifully furnished bedrooms with plush mattresses and hotel-style bedding • Private balcony • Bright and open layout • Fully equipped kitchen • Rooms with smart TV and high-speed Wi-Fi

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.

Relaxing Beachfront Cottage, 20min Ferry to Boston

Relax at this peaceful beachfront home. Just 30min to Gillete stadium! Ferry access to downtown Boston only a 5 minute walk and just a 20min ride to Boston. By far the best way to get in and out of the city. 3 story home with water on 3 sides, beautiful views and sunsets that will melt away all your stress. Kayaks and beach gear available, pet friendly. Weekly and Monthly Discounts