Holiday rentals with a kayak in Gloucester

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.

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.

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

Haskell Grove Estate

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.

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.

Oceanfront Dock Escape ~ Kayaks & Paddleboards

This 4-bedroom house is in a prime location & has EVERYTHING you need for an amazing vacation to Gloucester, MA! • 13-minute drive to Wingaersheek Beach • 10-minute drive to Downtown Main Street in Gloucester • 2 inflatable Paddleboards • 4 Kayaks Available! • Outdoor Patio w/ Oceanfront Views • Large Jenga set • Fully Stocked Kitchen • Multiple Outdoor Spaces: Balcony/Deck • Family Friendly- Pack n Play & High Chair • Beach Essentials: Chairs, Umbrellas, Life Vests, Towels

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.

mermaid surf bungalow on good harbor beach

This 3-bedroom, single-story bungalow makes for the ideal beach getaway. It has non-stop views of Good Harbor Beach and easy access to shopping, downtown, restaurants, a natural foods store, a great surf shop and, of course, the beach. Relax on the deck of this little oasis as you watch the sun rise and the tide roll in and out and listen to the birds sing. At high tide you can float out the back yard into the marsh on kayaks (we have 2) or your own paddle board.

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!