Holiday rentals with a kayak in Massachusetts

Relaxing Retreat | King Beds * Sauna * Bar Shed

Welcome to Cape Away, your charming family & pet-friendly retreat! Enjoy a fully stocked kitchen, cozy fireplaces, sauna, and outdoor shower. Unwind with dozens of board games, dart board, fire pit, and BBQ. The fully fenced private backyard offers beach gear, a bar shed and lounge area. We are perfectly located just 5–20 minutes from top rated restaurants and beaches, making it your ideal home base. With premium amenities, thoughtful touches it’s the perfect space to escape, explore and relax.

Sunset Lake studio apartment. Kayaks for use!

Beautiful sunsets over the lake! 2 adult kayaks and 2 kid kayaks are available to guests. Light a fire at night. Play some yard games (corn hole, Bocce or Molkky). We are walking distance to South Braintree Square. You will enjoy nature and still have close proximity to city. Walk to a super market, pharmacy, nail salon, bank, a tavern w/ live music. Other restaurants within walking distance include Mexican, Thai, Sushi, Italian, Vietnamese (pho), pizza and a great local coffee shop. 🛶 🌅 🌆

Lakefront, view of ski mtn, fireplace, sauna

Direct lakefront with panoramic views of Wachusett Mountain (#1 skiing in MA). In the summer, enjoy the kayaks, canoe, paddle-boards, motor boat. In the winter, cozy up next to the fireplace and enjoy a complimentary bottle of wine. In the fall, gaze upon the breathtaking foliage from the sunroom. Outdoor shower, dock, firepit, hammock, bike, washer/dryer, desk, sauna, dishwasher, linens, kitchen amenities. Our other lakefront house is down the road: www.airbnb.com/h/lakefrontmountainview

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.

Little Boho Retreat by the Beach

Kick back and relax in the most calming, low charm country, coastal cottage the town of Marion has to offer. You’ll experience spectacular view of the beach right from the deck to watching the boats from the harbor. Don’t just limit yourself to life at the beach in just the summer months, come and make memories in this beautiful year-round cozy cottage. It's a perfect retreat to go swimming, kayaking, fishing, bird/seal/crabs watching and more right here in a private community on Dexter Beach.

Hot Tub w/ Foliage Lake Views, Fire Pit & Kayaks

Congamond House is the perfect lake home getaway. Kayak the calm North Pond. Get your breathtaking pics of the surrounding wildlife. Cuddle up on the deck and enjoy the stars or relax in the hot tub under the deck while gazing upon the lake. This 1500 sq ft cottage is the perfect size for 2 families. (4 adults w/4 kids or 6 adults) Minutes from Six Flags Amusement Park, the Big E and the Basketball Hall of Fame 4 Kayaks that seat 6. Paddles and life vests provided 20 min. from Bradley Airport

Charming Pond-Front Boathouse

Charming antique boat house located directly on Long Pond. Quiet, peaceful accommodations with 180 views. Watch the American Bald Eagles and Osprey search for fish at dusk from your private deck that reaches out over the pond. Long Pond is full recreation, two kayaks and a canoe are available. Hiking, bicycling, golfing, fishing, swimming, boating, snorkeling, sunbathing, and napping are just a few of the activities that can be enjoyed in the quaint, semi-private, pond-front accommodation.

Romantic Cottage w/ Bikes, Paddle Boards & Kayaks

This newly remodeled, nautically themed cottage includes countless amenities designed for a fun, romantic getaway with all the comforts of home. - Bikes, paddle boards, 2-person kayak, yard games, beach chairs/towels & cooler - Outdoor fire pit and gas grill - Stocked kitchen with quality cookware, organic coffee/tea, water filtration pitcher + more - Organic, vegan, unscented, allergen-free soaps & cleaning products - Extreme COVID sanitation protocols as well as quarterly deep cleanings

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views

Welcome to our charming 3-bedroom lake cottage in Mendon, MA, where every sunrise paints the sky with breathtaking hues over tranquil waters. Accommodates 6 guests, making it ideal for families or couples seeking serenity. Enjoy lakeside coffee, fishing, kayaking, and evenings by the fire pit. We are pet-friendly, so feel free to bring your dogs along — if you have more than 1 dog, please let us know. Conveniently located near restaurants and attractions. Book now for a magical getaway!

Lakefront House/Private Dock/Year Round Hot Tub/AC

Beautiful cottage nestled on a half-acre of waterfront property on Swan Pond. The dock offers direct water access. Available are two kayaks, a canoe and two paddleboards. The kitchen offers beautiful views of the water while you enjoy your morning coffee. Local beaches are just minutes away. Enjoy the hammock, swings, hot tub, grill, outdoor fire pits and cocktails on the deck. Wanderers' Rest is located close to bike trails, boat rentals, movie theaters, restaurants, and bars.

Water front cabin-like guest suite on a quiet pond

Our home is located on a wooded lot overlooking a pristine kettle pond. Access to our home requires ascending a long but gradual set of stairs followed by a second set of stairs to the entrance of the guest suite. The two room suite has a bedroom and a kitchenette with a microwave, toaster, electric kettle and mini frig. There is a French press, coffee bean grinder, tea, cups, dishes and flatware in the cupboards. It does not have a full kitchen ( no stove/ no kitchen sink)

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.