Holiday rentals with a kayak in Wareham

Cottage in South Yarmouth

5 out of 5 average rating, 223 reviews

Serenity Views | Waterfront | KingBed | Kayaks SUP

Enjoy our cottage's charm and comfort with panoramic views and abundant sunlight. Comfortably hosts 2 families. Wake up to incredible sunrises. Lounge on the hammock or swim/fish/kayak in our beautiful backyard waterfront Long Pond. Explore the Cape in each direction: beautiful beaches and endless fun activities/interests. At the end of the day, enjoy dining on the deck as you grill. Sit back on the patio with a cocktail and gaze at the star filled sky and ambiance from the fire table. Welcome!

4.79 out of 5 average rating, 188 reviews

Guest suite in Pocasset

Rustic Beach Cottage

The salty air will instantly wash all your cares away. This rustic charming Cape get away is steps away from a quaint quiet picturesque beach. Simply relax in the comfortable surrounds in this fully furnished 1 bedroom Cottage apartment with all of your basic needs including WiFi, Smart TV, A/C, and a deck complete with gas grill and outdoor furniture offering you plenty of living space inside and out. Close to the bike paths, Cape Cod Canal, great restaurants, hiking, ferry and much much more!

4.87 out of 5 average rating, 213 reviews

Home in Brewster

Water Front Pond House - 3 acre Cape Cod Sanctuary

Extraordinary pondfront sanctuary on Cape Cod. 1300 sq.ft. home sleeps 8 in 3 bedrooms and 1 bath. Private dock and beach area. House is on the Pond and sited on 3 pristine acres - this property offers exceptional privacy with full water recreation opportunities while also being close to everything "Cape Cod". Centrally located in laid-back Brewster, 5 minutes to Bayside beaches, 10 mins to Chatham, Harwich Port, and Orleans. Local owners have 22 years of online vacation rental experience.

4.93 out of 5 average rating, 41 reviews

Cottage in Onset

Payton's Place is your beach get away.

Steps away from a beautiful beach, restaurants, ice cream and fine dining. There are two kayaks to take down to the waters edge and paddle around Shell Point. Close to fishing tours and canal cruising. Payton's Place has three bedrooms, two queen size beds and a full size sofa bed. The master bedroom has a deck with ocean views. Great for coffee to watch the sunrise or cocktails to watch the sunset. The house has an enclosed porch with glider to sit and chat after a long day at the beach.

4.99 out of 5 average rating, 175 reviews

Cottage in Marion

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.

5 out of 5 average rating, 161 reviews

Home in South Yarmouth

Relax w/ Amenities | 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, fire pit, and grill. The fenced backyard offers beach gear, paddle boards, and lounge area. We are perfectly located just 5–20 minutes from top spots, making it your ideal home base. With premium amenities, thoughtful touches like linens and towels provided, and space to relax and play, your perfect escape starts here.

4.85 out of 5 average rating, 149 reviews

Home in Buzzards Bay

Waterfront Cape Cod Family Home in Bourne

8 ACRES ON QUEEN SEWELL POND: Victorian Farm House on 8 acres +400 ft. of private shoreline. The shoreline accesses spring fed/sandy bottom pond with shady trees. Fish, Kayak or SUP. Across the pond is a sandy public beach. Enjoy the wrap around porch with rocking chairs and a wicker seating area. Plenty of space for everyone! Gourmet kitchen seats 10. Large rooms with spectacular pond views. Minutes to Cape Cod Canal, beaches and short drive to Plymouth, Falmouth and other Cape towns.

4.85 out of 5 average rating, 156 reviews

Cottage in Wareham

Onset beach, Cape code.Private Waterfront cottage

PRIVATE LAKE FOR YOUR Vacations year around. Spend quality time on spectaculars Blackmore pond.Comfortable cottage,step away from the water.Your own big dock out of your house as you wake up .Enjoy sunshine and sunset during summer , beautiful foliage , experience the ice or Snow drop during winter. this is exceptional romantic for your family . Well located next Onset beach, Water Park , Water Wizz of Cape Code. , Gate to Cape , To Ferry to Nantucket, Martha vineyard, Plymouth to P-Town

4.94 out of 5 average rating, 180 reviews

Cottage in East Falmouth

“Cozy Cottage” on Great Bay

Due to the coronavirus, we’re taking extra care to disinfect frequently touched surfaces between reservations.” Our Cozy waterfront cottage is located 120ft from great bay. Our closest beach is 2.5 miles and we are 4 miles from the center of town. Equipped with gas heat and Central A/C. We also have a gas fired fireplace to keep you cozy. Outside shower for days at the beach.We have one single kayak, two double Kayaks, a rowboat and a canoe for a scenic view of Great Bay. Quiet spot.

4.84 out of 5 average rating, 272 reviews

Cottage in Wareham

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

4.96 out of 5 average rating, 130 reviews

Cottage in Portsmouth

Waterfront, Dog-Friendly Cottage on the Cove

The cutest cottage on the cutest cove. Whether you’re into rosé & summer sun, hot chocolates in winter, a week off or a weekend away, Cove Cottage has water front views and a new dock to help you relax, unwind and enjoy the best of Aquidneck Island. One hour from Boston, and just 25 minutes to Newport, you have endless possibilities for what to do. Take out the kayaks or paddle board around the cove, dine in Newport or explore all Rhode Island has to offer!