
Holiday rentals with a kayak in Gloucester
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Gloucester
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

Sanctum by the Lake
Looking for a place to bring the family, or a get-a-away with friends? This is it! From the light and airy design that makes it feel like home to the large pool, hot tub, and lake access, The Sanctum by the Lake has everything you need for a great stay. It is a short 100 yard walk from the lake and a quick drive to Canobie Lake Park and Manchester Airport, 45 minutes to Boston or the NH Seacoast, close to the Lakes Region, White mountains, and great skiing spots as well as the famous NH Outlets.

Rockport 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

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.

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.

Downtown 1 bedroom w parking
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.

Large Private Guest House with Lake Views in 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) with additional queen futon. Unit is clean & comfortable with 2 smart tv's, wifi, Keurig, microwave, minifridge/freezer. Explore the lake using 2 available kayaks. Two public beaches nearby. Parking for 3 cars. Minutes from Canobie Lake Park & Tuscan Village. 5 Wedding venues w/in 5 miles. Short drive to NH seacoast, white mountains &foliage.

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.

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)

Gorgeous Waterfront Home with Dock and Beach
Looking for a wonderful location to enjoy a week this summer in Maine? We have a beautiful location right on the water for you and your family to enjoy. HAVE A BOAT and want to bring it with you? We have a deep water dock. Ask us about details and cost. House is on a dead end road. Come & enjoy the Maine coast! We are located 2 miles from Portsmouth, and there are numerous activities to do in this area. Golfing, Boating, Swimming, Outlet shopping and of course the Beach!

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.

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.

Little Lake House- Swimming, Fishing, 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.
Popular amenities for kayak rentals in Gloucester
House rentals with a kayak

Little Lakehouse, the Lookout

Northridge View

2BR cottage with fireplace, beach access, kayaks

Charming Carriage House on Historic Scenic Farm

Luxury Beach House Sleeps 16. Steps from the Sand.

Waterfront 4 bed/2 bath-Stunning Annisquam Sunsets

2 bedroom waterfront retreat all seasons

Ipswich Riverfront Lodge|Sleeps 10|Kayak+Canoe
Cottage rentals with a kayak

Tranquil Waterfront Retreat

Quaint Cobbetts Pond Cottage with Pond Views

Cottage with stunning ocean view and private beach

Waterfront Lake House on Cobbetts Pond!

Expansive coastal views, 3/2 newly renovated

Ponder Point waterfront cottage at Cobbetts Pond

Relaxing Beachfront Cottage, 20min Ferry to Boston

Cottage on the Water
Cabin rentals with a kayak

Peaceful Retreat at Onway Lake Resort

Cabin Fever

Little Lake, Big Fish - Fire Pit & Pvt Beach

Cohasset Woodland Cabin
Quick stats about holiday rentals with a kayak in Gloucester

Total holiday rentals
Explore 20 holiday rentals in Gloucester

Nightly prices starting at
Gloucester holiday rentals start at $141 SGD per night before taxes and fees

Verified guest reviews
Over 1,020 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Gloucester holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Gloucester rentals

4.9 Average rating
Gloucester stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with a firepit Gloucester
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- Rentals with beach access Gloucester
- Rentals with a kayak Essex County
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- Rentals with a kayak United States
- Hampton Beach
- Fenway Park
- TD Garden
- Harvard University
- Boston Common
- Ogunquit Beach
- Wells Beach
- Revere Beach
- Boston Seaport
- Boston University
- Freedom Trail
- New England Aquarium
- MIT Museum
- Long Sands Beach
- Boston Convention and Exhibition Center
- Gillette Stadium
- Canobie Lake Park
- Crane Beach
- Duxbury Beach
- York Harbor Beach
- Quincy Market
- Museum of Fine Arts
- North Hampton Beach
- Prudential Center




