Holiday rentals with a kayak in Essex County

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

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.

Ipswich Riverfront Lodge|Sleeps 10|Kayak+Canoe

Enjoy a secluded retreat in nature all while being conveniently close to all the North Shore has to offer at The Ipswich River Lodge. The rustic style combined with modern amenities and multiple gathering spaces makes this the perfect spot for groups and families alike. Just minutes to downtown Ipswich and Crane Beach/Estate it's the perfect landing spot to explore all that Cape Ann has to offer! 10 Min Drive to Crane Beach 30 Min Drive to Salem Experience Ipswich With Us & Learn More Below!

Parker River House! Riverfront Pet Friendly

Relax and unwind at this beautifully renovated 3-bedroom, 2-bath home on the Parker River. Excellent lay out for up to 4 adults and 5 children as well as one or two dogs. Just minutes from Newburyport, local beaches, and scenic coastal charm. Perfect for families, friends, or couples looking to experience the best of the North Shore. End your days in a cozy screened in porch relaxing and watching boats drift by, or by the fire pit while grilling dinner. 10 minute ride to the commuter rail.

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 Island View Escape in Southern NH

Enjoy Island View Escape on beautiful Big Island Pond. You will have exclusive use of the main house and share outdoor space with us and our dog. Swim, kayak, fish for bass, perch and more. Join us on our pontoon boat for a lake cruise. Use the gas grill and firepit by the lake or sit on the deck watching sunsets and listening to loons. Near Rt 93, it's an easy commute to the NH seacoast, the White Mountains and Boston. Restaurants, golf, tax-free shopping and walking trails are all close by.

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.

Forest Lodge at Haskell Gove Farm

Enjoy the natural beauty of the hillside forests, rocky monoliths, and the farm fields down to the marsh surrounding this getaway on 150 acre working equestrian estate. Easy access to hiking the Gloucester Watershed conservation lands, Wingaersheek Beach, Conomo Point, and downtown Essex Manchester, Gloucester, and Ipswich. Perfect for a corporate retreat or a family gathering. Located on Ebben Creek which overlooks iconic Choat Island. Perfect for boaters, can help with docking needs nearby.

Panoramic Ocean View; walk to private beach

🌟Waterfront home overlooking Ipswich Bay in Annisquam 🌟Balcony with panoramic ocean views 🌟On a 55 rolling acre estate of meadows, forest, marsh grass and granite shoreline 🌟The estate has walking paths that connect residents to various estate amenities, including two private beaches, a playground, and tennis court 🌟Board games and beach essentials included (towels, chairs, and umbrella) 🌟Outdoor shower 🌟Indoor wood fireplace 🌟BBQ grill 🌟Small work desk 🌟In unit washer and dryer

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.

Northridge View

Escape the everyday in this spacious, serene retreat on Great Neck. Wake to breathtaking sunrises and unwind with glowing sunsets. This three-level home offers a bright, fully equipped kitchen, dining area, comfortable bedrooms, and a full bath, plus sunny workspaces and a relaxing deck. Walk to private Clark Beach or public Pavilion Beach, and enjoy walking, biking, and kayaking. Seven miles from the stunning Crane Estate and Beach, with excellent restaurants and live music nearby.