
Holiday rentals with a kayak in Gloucester
Find and book unique kayak rentals on Airbnb
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 $168 SGD per night before taxes and fees

Verified guest reviews
Over 950 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!
Top-rated rentals with kayak in Gloucester
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

Lovely Waterfront Suite, New Hampshire Seacoast
Cozy waterfront one-bedroom suite on the New Hampshire Seacoast, perfect for a relaxing escape. Just minutes from Portsmouth and Durham, it’s ideal for a romantic getaway, attending a local event, or visiting the University of New Hampshire. Enjoy a private patio and waterfront deck featuring a seasonally heated dome and a year-round fire pit. A duraflame log for winter use in the living room fireplace. You’ll find many nice extras here.Peaceful coastal charm near the New Hampshire–Maine border.

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.

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

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.

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.

Lakefront Suite Two-Room, Comfy, Tranquil
Located on a lovely small lake, the upstairs suite has a panoramic view from the bedroom, a private spa-like bathroom, cotton linens, a comfy bed, A/C and a living room - it feels like an apartment, but no kitchen. Quietly watch lake nature or boats going by, or choose to swim, kayak, or fish. Enjoy industrial history at Lowell's National Park, take a forest walk nearby, or drive 10 min. to Nashua for its many restaurants, a casino, or tax-free shopping. We are one hour from Boston.

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!

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.

Little Lakehouse, the Lookout
Cozy up during your next trip to southern New Hampshire! The Lookout, situated right next to a serene lake, boasts luxury and spectacular water views. It's a perfect place for a peaceful escape or chance to experience the wide variety of seasonal New England activities from swimming to leaf peeping to ice fishing. The Little Lake house is a short drive to Canobie Lake Park and Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White mountains.

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.
Popular amenities for kayak rentals in Gloucester
House rentals with a kayak

The Beach Plum Cottage

Northridge View

Parker River House! Riverfront Pet Friendly

Luxury Beach House Sleeps 16. Steps from the Sand.

Waterfront 4 bed/2 bath-Stunning Annisquam Sunsets

Dotey Cottage: Walk to the Beach w/ Fenced in Yard

Beautiful Lake House with Private Beach

2 bedroom waterfront retreat all seasons
Cottage rentals with a kayak

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

Quaint Cottage near Cobbetts Pond
Cabin rentals with a kayak

Cabin Fever

Big Fish, Little Lake - Fire Pit & Pvt Beach

Cohasset Woodland Cabin

Rustic Log Cabin on Pawtuckaway Lake
Destinations to explore
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- Apartment rentals Gloucester
- Rentals with a firepit Gloucester
- Fitness-friendly rentals Gloucester
- Rentals with a fireplace Gloucester
- Beachfront rentals Gloucester
- Private suite rentals Gloucester
- Rentals with outdoor seating Gloucester
- Flat rentals Gloucester
- Rentals with beach access Gloucester
- Rentals with breakfast Gloucester
- Pet-friendly rentals Gloucester
- Rentals with an EV charger Gloucester
- Rentals with a washing machine and dryer Gloucester
- Rentals with a patio Gloucester
- Waterfront rentals Gloucester
- House rentals Gloucester
- Family-friendly rentals Gloucester
- Rentals with a kayak Essex County
- Rentals with a kayak Massachusetts
- Rentals with a kayak United States
- Fenway Park
- Harvard University
- Hampton Beach
- Ogunquit Beach
- Wells Beach
- TD Garden
- Gillette Stadium
- Boston Common
- Boston Seaport
- Revere Beach
- Boston University
- Boston Convention and Exhibition Center
- Long Sands Beach
- New England Aquarium
- Freedom Trail
- York Harbor Beach
- MIT Museum
- Canobie Lake Park
- Crane Beach
- Duxbury Beach
- Short Sands Beach
- Boston College
- North Hampton Beach
- Roxbury Crossing Station





