Vacation rentals with a kayak in Boston

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Top-rated kayak rentals in Boston

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Guest favorite

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

4.96 out of 5 average rating, 99 reviews

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.

Top guest favorite

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.

Guest suite in Tyngsborough

4.98 out of 5 average rating, 243 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.

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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

4.83 out of 5 average rating, 83 reviews

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. 🛶 🌅 🌆

Guest favorite

A two-story lake house is displayed, featuring large windows that provide views of Mirror Lake. A private dock is accessible from the water, with a patio area and seating arrangements visible. The property is surrounded by greenery, creating a serene atmosphere.

Home in Wrentham

4.94 out of 5 average rating, 67 reviews

Relaxing Waterfront Lake House

Relax at this peaceful, family-friendly lake house on Mirror Lake. Fully renovated 3-bedroom, 2 full bath getaway directly on the water with private deck, dock, patio area, propane grill, paddle boards, kayak, fishing, and more. Located nearby Gillette Stadium, Patriot Place, Wrentham Premium Outlets, Plainridge Park Casino, an abundance of restaurants, wedding venues, walking trails and central to Boston or Providence, this is a great location for many activities or just lounging by the water.

Top guest favorite

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

4.93 out of 5 average rating, 324 reviews

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.

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Cottage in Westford

4.92 out of 5 average rating, 36 reviews

Beach & pond cottage ! Westford MA and Boston!

Summer Village resort is only 20 miles from Boston. Best of both worlds! Your New England style cottage is steps to the beach, Lodge restaurant & bar, heated pools (family & adult), hot-tub, playground, tennis/ basketball/ fire pits pocket parks, golf putt, fishing, 24-hr fitness center. You'll enjoy lake views of Long Sought for Pond from the sun-filled porch, sandy beach, nestled in a beautiful gated seasonal cottage community. CENTRAL A/C !! Queen beds, Bunk bed. Weber outdoor grilling.

Top guest favorite

A wooden dock extends over calm waters, surrounded by lush greenery. Two red umbrellas provide shade over metal chairs. A blue inflatable float and a seating area enhance the inviting lakeside atmosphere. Steps lead down into the water from the dock for easy access.

Guest suite in Concord

4.98 out of 5 average rating, 126 reviews

Water front cabin-like guest suite on a quiet pond

Our home is located on a wooded lot overlooking a pristine kettle pond. Access to our home requires ascending a long but gradual set of stairs followed by a second set of stairs to the entrance of the guest suite. The two room suite has a bedroom and a kitchenette with a microwave, toaster, electric kettle and mini frig. There is a French press, coffee bean grinder, tea, cups, dishes and flatware in the cupboards. It does not have a full kitchen ( no stove/ no kitchen sink)

Top guest favorite

A private dock extends over gentle waters, complemented by two kayaks in a vibrant blue hue. The sun sets in the background, casting warm light across the scene, while a floating raft drifts nearby amidst lush greenery lining the shore.

Home in Gloucester

5 out of 5 average rating, 9 reviews

Waterfront 4 bed/2 bath-Stunning Annisquam Sunsets

Waterfront Paradise! Sweeping ocean river views & gorgeous sunsets! Swim, paddle board or watch the tides come and go on the private dock and raft. Enjoy a book, nap or meal on the screened-in porch or patio. Bring your own boat and cruise the day away. Close to beaches - Stage Fort (5 min) and Good Harbor (12 min) as well as cafes, shops and nightlife in town center (10 min).

Guest favorite

A wooden dock extends over a calm waterfront, leading toward the horizon where the water sparkles under sunlight. The shoreline features a mix of sand and rocky terrain, bordered by distant homes and trees on the left.

Guest suite in Lakeside Marblehead

4.91 out of 5 average rating, 270 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.

Top guest favorite

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

4.95 out of 5 average rating, 21 reviews

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.

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A tranquil view of Front Beach featuring soft sandy shores and gentle ocean waves. Sunlit homes line the horizon under a clear blue sky. The peaceful landscape suggests an inviting coastal setting, perfect for relaxation and enjoyment with family and friends.

Home in Rockport

5 out of 5 average rating, 3 reviews

Experience Classic New England-walk to beach&shops

- `* ` Spacious home near Rockport’s Front Beach, perfect for families or groups of friends. ** Ample indoor and outdoor space for relaxation and activities. ** Short walk to the beach, shops, galleries, and restaurants in downtown Rockport. ** Easy access to Gloucester’s dining options and whale watching tours (short drive away). ** Convenient walking distance to the commuter rail for trips to Boston or other North Shore seaside towns like Salem.

Top guest favorite

The exterior of a light-colored cottage is shown, featuring a sandy beach area and a well-maintained grassy area. A spacious deck with railings is visible, along with a sunlight-filled sky. Nearby structures can be seen in the distance, enhancing the coastal setting.

Guesthouse in Marshfield

4.98 out of 5 average rating, 81 reviews

Adorable 1 bedroom guest house with ocean view

Take it easy at this unique and tranquil getaway with an amazing ocean view. Enjoy the oversized deck for sunning, and grilling. 1 Queen bedroom and a pull out sleeper sofa in the family room with TV and WiFi. Kitchen includes basic appliances: mini-fridge, microwave, Keurig, toaster, toaster oven, air fryer, and portable cooktop. Amenities include use of sand volleyball court, linens and towels, window A/C, water toys, and 1 parking spot.