Holiday rentals with a kayak in Essex County

Find and book unique kayak rentals on Airbnb

Top-rated Accommodation with a Kayak in Essex County

Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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Top Guest favourite

A sunset over the lake creates a vibrant display of pinks and purples reflected in the calm waters. The surrounding trees frame the scene, enhancing the tranquility of the natural landscape.

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.

Outdoor spacesLocationNearby

4.96 out of 5 average rating, 130 reviews

Guest favourite

The living room features exposed wooden beams and a cozy seating arrangement. A plush sofa is accented with patterned cushions, while a decorative coffee table sits atop a soft area rug. Natural light filters through the windows, illuminating a rustic ambience.

Apartment in Rockport

Captains Quarters- Coastal Retreat Walk To Beach

Stay just steps from Rockport’s beautiful beaches, shops, and dining in this charming coastal retreat. Perfect for couples or small families, Captain’s Quarters offers comfort, convenience, and classic seaside charm in an unbeatable walkable location. Spend your days at Front Beach, exploring Bearskin Neck’s galleries and boutiques, or enjoying fresh seafood by the harbor — all within easy walking distance. Return to a peaceful space designed for relaxation after a day by the ocean. Inside you

ValueOutdoor spacesIndoor spaces

4.8 out of 5 average rating, 210 reviews

Guest favourite

A spacious living area is furnished with a large sectional sofa and two armchairs. Natural light fills the room through expansive sliding glass doors that open to an outdoor seating area. A cozy rug anchors the space, complemented by a wooden coffee table and bookcase lined with books.

Home in Ipswich

Ipswich Riverfront Lodge|Sleeps 10|Kayak+Canoe

Enjoy a secluded retreat in nature all while being conveniently close to all the North Shore has to offer at The Ipswich River Lodge. The rustic style combined with modern amenities and multiple gathering spaces makes this the perfect spot for groups and families alike. Just minutes to downtown Ipswich and Crane Beach/Estate it's the perfect landing spot to explore all that Cape Ann has to offer! 10 Min Drive to Crane Beach 30 Min Drive to Salem Experience Ipswich With Us & Learn More Below!

ValueLocationLayout

4.92 out of 5 average rating, 87 reviews

Top Guest favourite

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

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 largemouth Bass, Chain Pickerel, Brown Bullhead, or Sunfish. Welcome!

ValueLocationFamily

4.87 out of 5 average rating, 101 reviews

Top Guest favourite

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.

ValueOutdoor spacesHospitality

4.93 out of 5 average rating, 398 reviews

Top Guest favourite

A serene view of the calm lake is presented, framed by trees and surrounding greenery. The water reflects the clear sky, while homes are visible along the bank, creating a peaceful landscape perfect for relaxation.

Guesthouse in Salem

Lake Front Private Guest House in So. NH

Just 36 miles north of Boston/Logan Airport. Enjoy lake views from this above garage private entrance guest house. Two private bedrooms (1 queen/1 full) w/additional queen futon. Unit is clean & comfortable with 2 smart tv's, wifi, Keurig, microwave, minifridge/freezer. Explore lake using 2 available kayaks. Two public beaches nearby. Parking for 3 cars. Minutes from Canobie Lake Park, Tuscan Village & 5 popular wedding venues. Short drive to So Maine, NH seacoast, white mountains & foliage.

LocationOutdoor spacesGetting around

4.93 out of 5 average rating, 151 reviews

Top Guest favourite

Apartment in Marblehead

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, 1 queen pull-out couch Ample street parking available.

ValueLocationCheck-in

4.93 out of 5 average rating, 67 reviews

Top Guest favourite

A serene view of the lake is framed by two bright blue chairs and a small white table topped with a pot of yellow flowers. Lush greenery surrounds the water, with residential homes visible in the distance.

Home in Salem

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.

ValueLocationCheckout

4.94 out of 5 average rating, 197 reviews

Top Guest favourite

A historic estate stands on gently sloping green land, with a grand porch extending across the front. The building features a combination of stone and traditional architectural elements, surrounded by lush trees and open skies.

Home in Annisquam

Elegant Bayview Victorian Home; walk to beach

Discover the historic charm of Bayview, a stunning private estate once home to Civil War General Benjamin F. Butler. Spanning 55 acres of meadows, forest, and rocky shoreline, it features two pristine beaches: a white-sand crescent and a mica-strewn gem. Nestled in the quaint village of Annisquam, this peaceful family compound offers access to Plum Cove Beach, Halibut Point State Park, and vibrant Gloucester and Rockport. Indulge in fresh seafood, coastal beauty, and timeless serenity.

ValueOutdoor spacesCheck-in

4.98 out of 5 average rating, 59 reviews

Guest favourite

Home in Newbury

Parker River House! Nearby beaches, boat slip inc.

Relax and unwind at this beautifully renovated 3-bedroom, 2-bath home on the Parker River. Enjoy a spacious floor plan for family gathering and fun. Just minutes from Newburyport, local beaches, and scenic coastal charm, this home is perfect for families, friends, or couples looking to experience the best of the North Shore. End your days in a cozy screened-in porch, relax and watch boats drift by, or sit by the fire pit while grilling dinner. 10 minute ride to the commuter rail.

LocationOutdoor spacesCleanliness

4.89 out of 5 average rating, 9 reviews

Guest favourite

A bright and airy living area features large glass doors offering panoramic views of the water. Comfortable seating is positioned to take advantage of the scenic landscape, while light-colored walls enhance the spacious atmosphere. A ceiling beam adds architectural interest to the room.

Home in Ipswich

Northridge View

Escape the everyday in this spacious, serene retreat on Great Neck. Wake to breathtaking sunrises and unwind with glowing sunsets. This three-level home offers a bright, fully equipped kitchen, dining area, comfortable bedrooms, and a full bath, plus sunny workspaces and a relaxing deck. Walk to private Clark Beach or public Pavilion Beach, and enjoy walking, biking, and kayaking. Seven miles from the stunning Crane Estate and Beach, with excellent restaurants and live music nearby.

ValueLocationCleanliness

4.91 out of 5 average rating, 76 reviews

Guest favourite

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

LocationValueQuiet

4.94 out of 5 average rating, 48 reviews