Vacation rentals with a kayak in North Shore

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Top-rated kayak rentals in North Shore

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Top 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, 109 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.

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, 350 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.

Top guest favorite

A light-filled living area is arranged with a spacious sofa adorned with colorful cushions. A round coffee table sits at the center, complemented by a textured area rug. There are large windows allowing natural light, and decorative elements enhance the cozy ambiance.

Apartment in Rockport

4.98 out of 5 average rating, 102 reviews

Downtown w parking, beach, shops

Enjoy our fully refurbished historical home located in the heart of the coastal town of Rockport, Massachussetts. Perfect for couples or small families. This cozy basement unit offers a comfortable stay with with parking and a new kitchen, bathroom and washer and dryer, Our unit features a bedroom with a comfortable king size bed, The living space is tastefully decorated with a queen sofa bed. Walk to the beach, Bearskin neck, restaurants, Shalin Liu music center, art galleries and shops.

Top guest favorite

A vibrant blue cottage sits nestled among greenery, with a welcoming entrance and an American flag displayed. A dock with two kayaks rests at the water's edge, reflecting the serene lake. A patio area is visible on the upper deck, inviting relaxation.

Cottage in Northwood

4.94 out of 5 average rating, 128 reviews

Cottage on the lake! Includes kayaks & rowboat!

Super cozy, beautiful cottage right on the lake & dirt roads. Yard: sitting areas, propane fire pit, fenced in yard. Inside includes reading areas, dvds, wifi, books, coloring books, puzzles, games. Enjoy the rowboat & kayaks or bring your own boat. We are on Antique Ally and State Parks are nearby (2 miles away). Enjoy a day at Chucksters, Concord, Portsmouth or the lakes region. Enjoy the LAKE LIFE! No animals (Health concern for cleaner) 4 adults or 2 adults 3 kids. Life jackets provided

Top guest favorite

A dynamic scene showcases a gas fire pit, with flames dancing above dark stones. Two glasses are positioned on the edge, one filled with ice, the other with a warm beverage. The horizon displays a soft sunset over the water, adding a serene backdrop.

Guest suite in Dover

4.88 out of 5 average rating, 233 reviews

Lovely Waterfront Suite, New Hampshire Seacoast

Great location to enjoy the New Hampshire Seacoast. Just a few minutes to Portsmouth and Durham, perfect romantic getaway, or convenient spot to visit your student at the University of New Hampshire. Wonderful one bedroom suite, private patio. Enjoy the waterfront deck, have your breakfast or cocktail there. This is place is truly magical. You will enjoy how special it is. Close and convenient spot on the New Hampshire Maine boarder. New this summer an outdoor KITCHEN! Everything you’ll need

Top guest favorite

The studio features a spacious bed with white linens, accented by decorative throw pillows. A vibrant piece of art adorns the wall above the bed. A modern vanity area with a sink is visible, along with natural light filtering through windows that offer views of the surrounding woods.

Guest suite in Milford

5 out of 5 average rating, 133 reviews

New England Village Luxury Studio

Kick back and relax in this stylish studio! Our house is in a quiet neighborhood of older homes surrounded by woodlands yet conveniently located downtown, a half mile from our village green (Milford Oval). A short stroll over the river will take you to cafes, restaurants, pubs with live music, post office, library, shops & useful stores such as CVS. Whatever brings you…business, skiing, hiking, antiques, a family celebration or a romantic weekend away…we are looking forward to hosting you!

Top guest favorite

A wooden dock extends into a calm lake, with the reflection of the colorful sunset visible on the water's surface. Lights are strung along the dock, and a chair is positioned on the left side, creating a serene lakeside atmosphere.

Cottage in Mendon

4.94 out of 5 average rating, 105 reviews

Lake Front with Hot Tub and New Fitness Studio

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!

Top guest favorite

The cottage is nestled among vibrant autumn trees, framed by colorful foliage. A spacious deck overlooks the lake, with chairs offering seating options. The property includes a paved driveway and a dock area, with the water reflecting the surrounding nature.

Cottage in Weare

4.98 out of 5 average rating, 108 reviews

Lakeside cottage. Gorgeous view & several boats

Come and enjoy a relaxing stay at our peaceful cottage on Daniels Lake. The small, recently-renovated home is in a rural setting but close to restaurants, shopping, parks, ski slopes, golf courses, lakes and quaint New England villages. The large deck has a gorgeous view of the lake. Four kayaks, two canoes, standup paddle board and pedal boat are available to use on the lake which is known for its good fishing. Two bedrooms, dining room and living room overlook the lake and woods.

Top guest favorite

A tranquil kettle pond is depicted, reflecting the surrounding wooded landscape and soft hues of the sky. The calm water creates a mirrored surface, enhancing the serene atmosphere of the natural setting.

Guest suite in Concord

4.98 out of 5 average rating, 130 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)

Superhost

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.

Guest suite in Lakeside Marblehead

4.9 out of 5 average rating, 281 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 spacious patio with seating overlooks Pawtuckaway Lake, surrounded by lush greenery. A stone wall encircles the area, and a small beach transitions to the water's edge. The cabin features large windows, allowing natural light to illuminate the interior.

Cabin in Nottingham

4.99 out of 5 average rating, 176 reviews

Rustic Log Cabin on Pawtuckaway Lake

Our Cabin is located on Pawtuckaway Lake in Nottingham, NH where there is year round enjoyment! This is an older cabin built in 1970, with rounded logs and lots of warmth and charm. There is a beach area for swimming, patio for hanging out enjoying the views with a firepit as well as a dock for sunbathing and fishing. There is a public boat launch on the lake if you want to bring your own boat. Close to Pawtuckaway state park for hiking and mountain biking.

Top guest favorite

Vacation home in Derry

4.96 out of 5 average rating, 167 reviews

Little Lake House-fishing, relaxation, waterfront

Welcome to our home away from home. This cozy lake get away just minutes over the border from Massachusetts is the perfect place to connect with friends and family. Enjoy days out on the water which is right outside your back door! Or nights at the fire pit enjoying the stars. We have wifi, tv w/ streaming services, laundry, a/c & heat, and kayaks to make your stay as comfortable and fun as possible. We're family friendly and have a crib for infant/baby.