Vacation rentals with a kayak in Essex County

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Top-rated kayak rentals in Essex County

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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

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, 326 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 scenic view of Big Island Pond is visible from a deck adorned with a table and two chairs. The calm waters reflect the surrounding greenery, while boats are moored along the shore. Bright flowers in a planter add a pop of color to the outdoor space.

Home in Derry

5 out of 5 average rating, 13 reviews

Lakefront Island View Escape in Southern NH

Enjoy Island View Escape on beautiful Big Island Pond. You will have exclusive use of the main house and share outdoor space with us and our dog. Swim, kayak, fish for bass, perch and more. Join us on our pontoon boat for a lake cruise. Use the gas grill and firepit by the lake or sit on the deck watching sunsets and listening to loons. Near Rt 93, it's an easy commute to the NH seacoast, the White Mountains and Boston. Restaurants, golf, tax-free shopping and walking trails are all close by.

Superhost

A cozy seating area features two armchairs facing large windows that provide a clear view of the lake. Natural light enters, illuminating the wooden floor and a round coffee table adorned with a small plant. The decor emphasizes tranquil lakefront living.

Home in Amesbury

4.91 out of 5 average rating, 55 reviews

2 bedroom waterfront retreat all seasons

Take it easy at this unique and tranquil getaway right on the lake. AMAZING lake views! Enjoy taking the canoe out for a day of fishing from your backdoor or lounge in the backyard with a good book. Feeling adventurous ? - a quick drive and you can be at many nearby beaches ( Plum island, Salisbury, Hampton) or in downtown newburyport or Portsmouth for a day of sightseeing/shopping. Lake Attitash is a popular fishing spot for longemouth Bass, Chain Pickerel, Brown Bullhead, and Sunfish.

Top guest favorite

Bungalow in Newburyport

5 out of 5 average rating, 114 reviews

The Bungalow Luxe & Cozy Retreat by the Sea

The Bungalow is a coastal chic dream built for two! A newly updated & thoughtfully designed gem, nestled at the northern-most point of Plum Island, Newburyport, MA (not more than 100 paces from the ever watchful beacon of the famous Plum Island Lighthouse). Whether relaxing at the beach, paddling around the Basin, biking to one of the island stores or restaurants , or simply exploring the pristine Federal Wildlife Refuge, a special experience & adventure awaits you at The Bungalow!

Guest favorite

Home in Salem

4.95 out of 5 average rating, 149 reviews

Quaint Little New Hampshire Lake House Getaway!

Imagine the peace and quiet of looking out a wall of glass seeing the tranquility of the lake while knowing 10 minutes away is shopping, restaurants entertainment and just about anything you could ask for to meet your needs. 10 minutes from the highway, 35 minutes from Boston, 35 minutes from the ocean and 1 1/2 hours from the mountains. We are a central point to anything you’re looking for. Newly renovated lake house with all the up to date amenities. Come and enjoy a night or week.

Superhost

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

5 out of 5 average rating, 3 reviews

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

Top guest favorite

A scenic backyard leads down to the water, featuring a seating area with four chairs and a table. Green foliage surrounds the manicured lawn, which extends toward the river. A boat can be seen on the water, with inflatable items floating nearby, all set against a cloudy sky.

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, 271 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.

Superhost

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, 4 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

Brightly colored kayaks in shades of red and yellow are lined up on a sandy area. The calm water of the harbor is visible in the background, with boats and colorful umbrellas dotting the shoreline under a clear blue sky.

Home in Lakeside Marblehead

5 out of 5 average rating, 56 reviews

Dotey Cottage

Just a short walk to Devereux Beach and centrally located in town, Dotey Cottage is a newly-renovated getaway for those looking to enjoy Marblehead, Salem and Boston's North Shore. You'll have the entire cottage to yourself, so whether you choose to relax in the fenced in backyard, kayak at Riverhead beach, or walk to the movie theater or restaurants close by, you'll have all you need to enjoy your stay!

Top guest favorite

A modern house is situated by the lake, featuring a spacious deck with multiple large windows that provide views of the water. A staircase leads from the deck down to a dock area, which is lined with natural rocks, enhancing the lakeside setting.

Guest suite in South Hamilton

4.96 out of 5 average rating, 284 reviews

It’s better to wake at the Lake 2BR guest suite

Overlooking Chebacco Lake, your rooms are downstairs in a private level. There are 2 bedroom available for use downstairs along with a big living area a coffee/tea bar and a bathroom with shower on this level. You can access to the lake for swim, kayak, canoe or if you come in the winter you can icefish, ice skate, cross country ski or snowshoe too.