Holiday rentals with a kayak in Plymouth County

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.

Pelicans Bog on Woods Pond in Middleboro

Centrally located in Middleboro, this 3 bedroom house on Woods Pond is in a private community. Enjoy the massively spacious out door space while you fish directly off your private dock in the water. Kayak the pond with 2 tandem kayaks provided. Enjoy breezy dinners on the elevated deck overlooking the pond. There is an Air Hockey table located just off the basement bonus room or the foosball table inside. A dedicated large office space fully equipped and minutes to MBTA 1 hour to Boston.

Ocean View Humarock Beach Cottage

Quintessential Humarock Beach cottage just steps from the ocean. Wake up to sea breezes, enjoy sunset walks along the shoreline, and experience one of the South Shore’s most relaxing coastal escapes. Perfect for both relaxation and adventure, the cottage doubles as a sports haven with a beach volleyball court and includes use of kayaks and paddleboards for exploring the coastline and the river. Spend your days on the sand, in the water, or unwinding on the deck as the ocean breeze rolls in.

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.

Clear Pond Pet Friendly Retreat

Welcome to our beautifully renovated pondfront retreat —Private Residence on a Pondfront Estate. The perfect peaceful getaway experience near Plymouth that comfortably sleeps six! This pet-friendly escape offers the best of relaxation and outdoor adventure all in one place. Enjoy kayaking, boating, and fishing right from your private beachfront along the pond. Spend your mornings walking the scenic trails with your dogs, and your evenings gathered around the fire pit under the stars.

Waterfront Pond House – Private & Peaceful Getaway

🌿✨ ESCAPE TO YOUR LAKESIDE PARADISE ✨🌿 Wake up to breathtaking lake views 🌅 and the peaceful sounds of nature at this serene lakeside retreat. This home offers the perfect blend of tranquility + adventure. 🚣 Lake Adventures Await – Paddle out on the water with kayaks or cruise around on the 🚲 pedal boat for unforgettable lake days. 🔥 Evenings Under the Stars – Unwind on the patio by the outdoor fire pit ✨🌲 Book your stay today and experience the magic of lake life firsthand! 🌲✨

Cape Cod; John’s Pond beach w/2 kayaks -SuperHost!

Welcome to our Cape house! Amazing neighborhood & the perfect spot to explore the Cape. Located on fully recreational John's Pond with your private association beach at the end of the street. Large sandy beach, boat launch, float, playground and tennis courts - plus enjoy use of our two kayaks! Just 10 min to South Cape ocean Beach & Mashpee Commons. The house is FULLY updated with hardwoods throughout, AC's, laundry room, front deck with views, private back patio with fire pit and patio.

Sunset LAKE VIEW studio. Recently upgraded!

Welcome to Sunset Lake! Enjoy beautiful sunsets year round! Cozy in the winter with plenty of extra blankets and a great heating system! Light a fire at night. 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 Bliss,Your Perfect Getaway on the Water.

Welcome to our charming lakefront Airbnb! Nestled on the shores of Monponsett lake, this cozy retreat offers breathtaking views and a peaceful escape from the hustle and bustle of everyday life. With comfortable accommodations for up to 6 guests, our Lake front features a fully equipped kitchen, a spacious living Room, fireplace, private deck overlooking the water. Enjoy a morning coffee as the sun rises over the tranquil lake, or unwind in the evening with a bonfire by the shore.

Beautiful Lakeside Apt between Boston and Cape Cod

Beautiful apartment, with extraordinary lake views, located on a quiet street and midway between Boston and Cape Cod. Access to the lake is just feet from your back door. Enjoy grilling, swimming and the use of kayaks, canoe and standup paddle boards. 1 bed, 1 bath, can sleep 5 with a pull out queen and twin couches. Full kitchen, laundry, internet, cable. Your own access with keypad and off street parking is an added bonus. NO SMOKING OF ANY KIND IN OR OUTSIDE-NO EXCEPTIONS.

Cozy Cottage on a Private Pond

This cozy cottage is located on a private 42 acre, spring fed, crystal clear private pond. Enjoy kayaking, swimming or fishing from the dock or just relax on the deck overlooking the pond. Sleeps 5 in 2 bedrooms and trundle bed in the 4 season room. There is good fishing and canal cruises, cafes and restaurants close by and a summer concert series in park. Many of our guests with children have visited Edaville Railroad and "Thomasville" It is about 15 miles from the cottage

Pondside Plymouth Cottage | Kayaks & Fire Pit

Charming 2BR, 1BA cottage on Great Herring Pond in South Plymouth. Enjoy classic New England summer living with a large fenced yard, spacious deck, screened-in porch for outdoor dining, outdoor shower, kayaks, fire pit, swing set, and peaceful pond views. Walk to a private deeded beach for swimming or relaxing, with easy access to nearby beaches, downtown Plymouth, and Cape Cod. Please note: Due to a severe allergy, this is a pet-free property, including service animals.