
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 $187 AUD 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 and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Gloucester holiday 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!
Top-rated Accommodation with a Kayak in Gloucester
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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

Gorgeous Lakefront Suite Apartment (Unit 3)
Get away to a lakefront retreat in beautiful southern NH! Enjoy our 1 bedroom unit that is part of a gorgeous 3 family waterfront home. This suite comes complete with a thoughtfully decorated living room, a stocked kitchen, and furnished with a queen-sized bed and an air mattress upon request. Enjoy free shared lake access! It is 8 minutes from I-93 and a short drive to Canobie Lake Park, Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White Mountains.

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.

Haven 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 hot tub, loft room, and lake access, The Haven 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.

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.

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.

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.

Luxury Beach House Sleeps 16. Steps from the Sand.
This beautiful beach house sleeps up to 16 people and is only a short walk to the beach and everything Hampton beach has to offer. The house has decks all around it to watch the sunset and a fenced in backyard for games and grilling. This house has three levels so guests have ample space, and central AC to keep you cool during hot summer day, a fully stocked kitchen with all you need for home made meals. Come relax and unwind at this Beach House!
Popular amenities for Gloucester kayak rentals
Holiday House Rentals with a Kayak

The Beach Plum Cottage

Northridge View

Parker River House! Riverfront Pet Friendly

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

Ipswich Riverfront Lodge|Sleeps 10|Kayak+Canoe
Cottages 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 Cottage on Cobbetts Pond!

Relaxing Beachfront Cottage, 20min Ferry to Boston

Cottage on the Water

Quaint Cottage near Cobbetts Pond

Lake House
Cabin rentals with a kayak

Cabin Fever

Big Fish, Little Lake - Fire Pit & Pvt Beach

Cohasset Woodland Cabin

Rustic Log Cabin on Pawtuckaway Lake
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- Rentals with a kayak Essex County
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- 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
- Freedom Trail
- New England Aquarium
- MIT Museum
- York Harbor Beach
- Canobie Lake Park
- Short Sands Beach
- Duxbury Beach
- Crane Beach
- North Hampton Beach
- Boston College
- Northeastern University





