Vacation rentals with a kayak in Boston

4.96 out of 5 average rating, 102 reviews

The exterior of the cottage is visible, showcasing natural wood siding and a brick patio leading to the entrance. Lush greenery surrounds the property, while a glimpse of Chebacco Lake is seen in the background, contributing to a calm and inviting environment.

Cottage in Essex

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.

Guest suite in Tyngsborough

A serene lakeside view captures a vibrant sunset with the sun partially descending behind distant hills. A lone fisherman in a boat is visible on the water, while a wooden deck features seating arrangements surrounded by lush plants.

4.98 out of 5 average rating, 245 reviews

Lakefront Suite Two-Room, Comfy, Tranquil

Located on a lovely small lake with a panoramic view from the bedroom, private spa-like bathroom, cotton linens, a comfy bed, A/C and a living room-so not an 'entire' home but more than just a room! Quietly watch lake nature or boats going by, or choose to swim, kayak, or fish. Enjoy industrial history at Lowell's National Park mills, take a forest walk nearby, or drive 10 min. to Nashua for its many restaurants and tax-free shopping. 1 hr from Boston and near many New England highlights.

4.84 out of 5 average rating, 87 reviews

A sliding glass door frames a view of the lake, providing access to a grassy area with several outdoor chairs arranged for relaxation. Soft natural light illuminates the space, and a patio area is visible through the open door.

Guest suite in Braintree

Sunset Lake studio apartment. Kayaks for use!

Beautiful sunsets over the lake! 2 adult kayaks and 2 kid kayaks are available to guests. Light a fire at night. Play some yard games (corn hole, Bocce or Molkky). 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. 🛶 🌅 🌆

4.93 out of 5 average rating, 331 reviews

The entrance features a welcoming porch with white railings, flanked by colorful flower pots and hanging baskets. A brightly painted totem pole adds a touch of character beside a neatly manicured garden. The well-kept pathway leads to a white door, inviting guests inside.

Apartment in Medford

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.

4.88 out of 5 average rating, 25 reviews

A welcoming entrance is displayed with a polished brick pathway leading to a well-maintained white house. The front features large black-framed windows and a pair of bold red doors flanked by pots of colorful flowers, complemented by lush green landscaping.

Home in Canton

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.

4.89 out of 5 average rating, 9 reviews

A private back patio is featured, adorned with a wooden deck and steps leading to a paved area. Outdoor seating arrangements include a blue couch and armchair. A grill is positioned nearby under a pergola, accompanied by decorative string lights that enhance the ambiance.

Home in Beachmont

Revere Beach House, Logan Airport, Bay Views

Steps from Revere Beach, this home sleeps 6+ with sunrise views! Enjoy a private patio with firepit, grill, master suite with tub, and basement entertainment: 60" TV, wet bar, board & card games. 15 mins to Logan Airport (Uber ~$20). Fast WiFi, multiple WFH setups, full loaded kitchen, laundry w/detergent, parking for 2-4. Upstairs: king suite, queen & twin bedrooms rooms, office. Beach towels, 2 kayaks, linens, soaps all included. Relax by the fire or paddle out—your perfect getaway awaits!

5 out of 5 average rating, 14 reviews

An outdoor seating area features a modern fire pit with a glass barrier, providing warmth and ambiance. The background displays a illuminated heated igloo, enclosed by a white fence, adorned with soft lights for evening enjoyment. A decorative throw pillow with 'CUDDLE' text is placed on the sofa.

Home in Waltham

Brand New Boston 6BR 5.5 Bath-IGLOO,Arcade,Parking

Luxurious 6 Bedroom 5.5 bath Modern Villa with Game Room, Pool table, Air hockey, Movie Projector, EV charger, Fire Pit, Heated Garage, ITS OWN HEATED IGLOO and much more! Indulge in the epitome of modern living in our 4300+ sq.ft newly constructed villa 20 mins from Boston. The state-of-the-art kitchen features high-end appliances, sleek quartz countertops, a large center island, and everything you need to prepare gourmet meals. Experience comfort, luxury, and fun book your stay today!

5 out of 5 average rating, 9 reviews

A charming blue house is positioned over water, featuring multiple outdoor spaces. An expansive deck is visible with a red umbrella and seating, while two kayaks rest on a nearby floating dock. Surrounding greenery enhances the natural setting.

Home in Gloucester

Oceanfront Dock Escape ~ Kayaks & Paddleboards

This 4-bedroom house is in a prime location & has EVERYTHING you need for an amazing vacation to Gloucester, MA! • 13-minute drive to Wingaersheek Beach • 10-minute drive to Downtown Main Street in Gloucester • 2 inflatable Paddleboards • 4 Kayaks Available! • Outdoor Patio w/ Oceanfront Views • Large Jenga set • Fully Stocked Kitchen • Multiple Outdoor Spaces: Balcony/Deck • Family Friendly- Pack n Play & High Chair • Beach Essentials: Chairs, Umbrellas, Life Vests, Towels

Guest suite in Lakeside Marblehead

A light-filled living area features a pull-out sofa adorned with striped cushions and a coffee table with a decorative book and lamp. A sliding glass door opens to a sleeping area with a spacious bed, while bright curtains frame the window, offering a view of the exterior.

4.9 out of 5 average rating, 272 reviews

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.

4.95 out of 5 average rating, 21 reviews

A three-story house is depicted, showcasing a light-colored exterior and a welcoming front porch. Grassy beach access is visible in the foreground, and power lines extend across the skyline, adding a unique perspective to the coastal setting.

Home in Hull

Every room a water view updated kitchen & bath

Make some memories at this unique and family-friendly place. 5 minute walk to commuter boat/ferry to Boston, Ma/Logan airport. Ferry ride is 15-30 minutes depending if boat is direct to Boston, MA or stops at Logan or Hingham. Please check ferry schedule as it changes to weekday only in the off season. The house is 28 miles south of Boston. Panoramic water views. Beach access across the street. Vacation or work from home with water views from every window.

4.72 out of 5 average rating, 106 reviews

An inviting living area features a black sofa adorned with red and white cushions, complemented by two matching lounge chairs. A round coffee table occupies the center, set atop a patterned area rug. Natural light enters through two windows, enhancing the room's warm tones.

Guest suite in Canton

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.