Vacation rentals with a kayak in Essex County

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Top-rated kayak rentals in Essex County

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Top guest favorite

Home in Gloucester

4.95 out of 5 average rating, 40 reviews

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!

Top guest favorite

The exterior of the cottage is visible, showcasing natural wood siding and a brick patio leading to the entrance. Lush greenery surrounds the property, while a glimpse of Chebacco Lake is seen in the background, contributing to a calm and inviting environment.

Cottage in Essex

4.96 out of 5 average rating, 111 reviews

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.

Guest favorite

A serene lakeside view captures calm waters reflecting the surrounding greenery. A private dock extends into the lake, providing access for boating. Lush grass leads to the dock, with a few scattered pebbles and plants visible along the edge.

Home in Amesbury

4.91 out of 5 average rating, 67 reviews

2 bedroom waterfront retreat all seasons

Take it easy at this unique and tranquil getaway right on the lake. AMAZING lake views! Enjoy taking the canoe out for a day of fishing from your backdoor or lounge in the backyard with a good book. Feeling adventurous ? a quick drive and you can be at many nearby beaches ( Plum island, Salisbury, Hampton) or in downtown Newburyport or Portsmouth for a day of sightseeing/shopping. Lake Attitash is a popular fishing spot for largemouth Bass, Chain Pickerel, Brown Bullhead, or Sunfish. Welcome!

Guest favorite

The entrance features a welcoming porch with white railings, flanked by colorful flower pots and hanging baskets. A brightly painted totem pole adds a touch of character beside a neatly manicured garden. The well-kept pathway leads to a white door, inviting guests inside.

Apartment in Medford

4.93 out of 5 average rating, 351 reviews

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.

Top guest favorite

Apartment in Rockport

4.98 out of 5 average rating, 106 reviews

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.

Guest favorite

A serene view of the calm lake is presented, framed by trees and surrounding greenery. The water reflects the clear sky, while homes are visible along the bank, creating a peaceful landscape perfect for relaxation.

Guesthouse in Salem

4.93 out of 5 average rating, 111 reviews

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.

Guest favorite

Guest suite in Hamilton

4.93 out of 5 average rating, 68 reviews

Spectacular pond view, suite on conservation land

Imagine sipping morning tea or coffee gazing at the view of the pond across the street. Or maybe relaxing in a screen porch watching yellow finches and hummingbirds flittering around the yard in season. Explore the trails on 180 acres of conservation land out our backdoor. Delight in the changing colors of leaves in the fall, and the sounds underfoot. After exploring Cape Ann or our award winning beaches, or dining on fresh New England seafood, how about a sunset canoe ride on the pond?

Superhost

The cozy suite features a light-colored queen bed with decorative pillows, accented by a dark blue feature wall. A compact kitchenette with wooden cabinetry is seen alongside the bed, offering essential amenities. Soft lighting creates a warm ambiance, complemented by a nearby window dressed in light curtains.

Guest suite in Lakeside Marblehead

4.81 out of 5 average rating, 37 reviews

Harborside Hideaway Guest Suite

Charming, private guest suite attached to a historic Colonial in the heart of Old Town. Guests love its quintessential New England charm and prime location. Take in stunning coastal views just steps outside the door of your private entrance. Walk or bike to shops, bars/restaurants/cafes, beaches & historic landmarks. Minutes to bus & commuter rail. Great for couples, solo travelers, visiting professors, or parent(s) with infant or young kids. Please inquire about accommodation options.

Guest favorite

Home in Salem

4.94 out of 5 average rating, 169 reviews

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.

Guest favorite

Home in Ipswich

4.92 out of 5 average rating, 52 reviews

Northridge View

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.

Superhost

A light-filled living area features a pull-out sofa adorned with striped cushions and a coffee table with a decorative book and lamp. A sliding glass door opens to a sleeping area with a spacious bed, while bright curtains frame the window, offering a view of the exterior.

Guest suite in Lakeside Marblehead

4.9 out of 5 average rating, 284 reviews

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.

Guest favorite

An aerial view captures a spacious coastal home, surrounded by lush trees with changing leaves. The structure showcases a wraparound deck, and the sloped lot offers a rocky edge, enhancing the natural setting. Nearby residences are partially visible through the foliage.

Apartment in Rockport

4.93 out of 5 average rating, 168 reviews

Hidden Gem! Short term rental steps from 2 beaches

Hidden Gem! Short term seaside rental. Lovely 1 bed 1 bath unit located on private wooded property, steps away from 2 beaches. Private unit amenities include deck with gorgeous year round views of the Atlantic. Fully equipped kitchen, flat screen TV, WiFi, and everything to make your stay pleasant and comfortable. We're a 7 minute drive from downtown Rockport and Gloucester, a 7 minute walk to Cape Hedge and Long Beaches.