
Vacation rentals with a kayak in Gloucester
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Top-rated kayak rentals in Gloucester
Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

Private Beach!
Private Beach Dream vacation! No dealing with big crowds and parking fees to be at the beach! Step out to a sandy beach right in front of the comfort of your beautiful Coastal House. When you are on vacation you want to feel in paradise and that is how you will feel at this house! The house offers 3 bedrooms, 1 full bathroom, laundry, fully equipped kitchen and living room that walks out to an amazing water view deck and parking for 2 cars. I forgot to mention the most incredible sunsets ever!

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.

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 w parking, beach, shops
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.

Big Lakehouse /beach, dock, hottub, deck +
Cozy up during your next trip to southern New Hampshire! The Big Lakehouse, 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 and leaf peeping to ice fishing. The Big 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.

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.

Northridge Vista
Forget your worries in this spacious and serene space. Enjoy sunrises and sunsets over the ocean! Choose your workspace or relax with a book on the deck. Contemporary three level house….kitchen, dining room, bedroom and bathroom on middle level. Walking distance to private Clark Beach and public Pavillion Beach. Great walking, biking and kayaking. Seven mile drive to the spectacular Crane Estate and Crane Beach. Variety of different excellent restaurants and music venues in the area.

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-fishing, relaxation, 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
House rentals with a kayak

Waterfront House on Plum Island with Great View

The LiKenSco Farm/Beach House

Dotey Cottage

Private Waterfront home

Big Island Pond Lake House Hampstead

2 bedroom waterfront retreat all seasons

Elegant Bayview Victorian Home; walk to beach

Lakeside at Sunset Point
Cottage rentals with a kayak

Relaxing Beachfront Cottage, 20min Ferry to Boston

*Cozy 2 bdrm Cottage (Pet Friendly)*

Quaint Cottage near Cobbetts Pond

Lakefront! Johnson Point Cottages-“Summer Breeze”

Quaint Cobbetts Pond Cottage with Pond Views

Cottage with stunning ocean view and private beach

Waterfront LakeHouse on Cobbetts!
Other vacation rentals with a kayak

Captain Kimball House

Plum Island Beach House - All Decked Out!

Little Lake, Big Fish - Fire Pit & Pvt Beach

3BR or 4BR Beachfront Home-Ocean View from 3 BR's!

Le Elona – Private Island Stay on Historic Land

Hot Tub|Fire Pit|Electric Bikes|Projector|Garage

Airstream & Ocean View: Unique Gloucester Getaway

Fresh Clean Annisquam Cottage
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 $160 per night before taxes and fees

Verified guest reviews
Over 860 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!
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- Rentals with a kayak Essex County
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- Rentals with a kayak United States
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