
Vacation rentals with a kayak in Gloucester
Find and book unique kayak rentals on Airbnb
Top-rated kayak rentals in Gloucester
Guests agree: these kayak rentals 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.

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.

Harborside Retreat on Bearskin Neck
Experience true seaside living at this private retreat perched at Rockport Harbor. Enjoy coffee on your patio as boats drift by and take in peaceful harbor views from one of Rockport’s most iconic locations. Step outside to beaches, art galleries, boutiques, and fresh seafood dining — all just moments away on foot. Perfect for couples or small families seeking a relaxing coastal escape. Inside, historic charm meets modern comfort with exposed beams, a welcoming living space, and a full kitchen

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.

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.

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 Gloucester kayak rentals
House rentals with a kayak

Beautiful Waterfront Retreat steps to downtown

Northridge View

Riverfront, pet friendly, near Newburyport

Harmony Cove Cottage

Waterfront 4 bed/2 bath-Stunning Annisquam Sunsets

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

Big Island Pond Lake House Hampstead

2 bedroom waterfront retreat all seasons
Cottage rentals with a kayak

Staycation + Work From Home in one private setting

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

Cabin Fever

Big Fish, Little Lake - Fire Pit & Pvt Beach

Little Lake, Big Fish - Fire Pit & Pvt Beach

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

Total vacation rentals
Explore 20 vacation rentals in Gloucester

Nightly prices starting at
Gloucester vacation rentals start at G$27,162 GYD per night before taxes and fees

Verified guest reviews
Over 950 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Gloucester vacation rentals include wi-fi 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!
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- Québec City Vacation rentals
- Rentals with a fire pit Gloucester
- Beachfront rentals Gloucester
- Condo rentals Gloucester
- House rentals Gloucester
- Family-friendly rentals Gloucester
- Fitness-friendly rentals Gloucester
- Pet-friendly rentals Gloucester
- Apartment rentals Gloucester
- Rentals with beach access Gloucester
- Rentals with a washer and dryer Gloucester
- Rentals with breakfast Gloucester
- Rentals with an EV charger Gloucester
- Rentals with outdoor seating Gloucester
- Waterfront rentals Gloucester
- Private suite rentals Gloucester
- Rentals with a fireplace Gloucester
- Rentals with a patio Gloucester
- Rentals with a kayak Essex County
- Rentals with a kayak Massachusetts
- Rentals with a kayak United States
- Hampton Beach
- Fenway Park
- TD Garden
- Harvard University
- Boston Common
- Ogunquit Beach
- Wells Beach
- New England Aquarium
- Revere Beach
- Boston Seaport
- Northeastern University
- Boston University
- Gillette Stadium
- Freedom Trail
- Boston Convention and Exhibition Center
- Long Sands Beach
- MIT Museum
- Canobie Lake Park
- Crane Beach
- York Harbor Beach
- Duxbury Beach
- Quincy Market
- Roxbury Crossing Station
- Museum of Fine Arts





