Vacation rentals with a kayak in Wareham

5 out of 5 average rating, 177 reviews

An outdoor dining setting features a table with a plate of salad and wine glasses, accompanied by a bottle of white wine. In the background, a charming shed displays ‘Cape Away’ signage, surrounded by well-maintained greenery and a cozy lounge area.

Home in South Yarmouth

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.

4.79 out of 5 average rating, 194 reviews

A calm waterway reflects soft pastel colors during sunrise, with silhouettes of boats anchored in the distance. Gentle grasses line the foreground, and the tranquil landscape is framed by hills on the horizon, offering a serene morning view.

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!

4.86 out of 5 average rating, 219 reviews

A wooden dock extends into a serene freshwater pond, surrounded by lush green foliage. The calm water reflects the clear blue sky and distant tree line, creating a tranquil setting for relaxation and outdoor activities.

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.

4.99 out of 5 average rating, 195 reviews

The cottage exterior is illuminated by warm lights, showcasing a spacious deck with inviting seating. Lush greenery surrounds the property, with a vibrant purple flowering bush nearby. The serene atmosphere is enhanced by the evening sky, providing a cozy and welcoming retreat.

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.

4.98 out of 5 average rating, 206 reviews

A serene view of a crystal clear pond is framed by lush trees. The calm water reflects the blue sky and scattered clouds, creating a tranquil atmosphere. A wooden pathway leads to the water's edge, inviting exploration and relaxation.

Cottage in Dennis

★Waterview ★Pet Friendly ★Kayaks ★Trails ★

Welcome to SEAGLASS COTTAGE! 🔸 200 MBPS WIFI 🔸 Steps to sandy beach on a crystal clear pond 🔸 Pet friendly 🔸 Linens & towels are included. Beds will be made 🔸 Swim, fish or use our 2 kayaks & 2 SUP’s 🔸 Bluestone private patio w/waterviews+charcoal BBQ 🔸 Outdoor shower 🔸 Sunroom w waterview 🔸 Washer+dryer 🔸 Fully equipped kitchen w/Carrera marble counter 🔸Gas firepit 🔸Ductless A/C & Heat 🔸Small library of books, didn't finish the book? Take it! 🔸Pet fee $25/day

4.94 out of 5 average rating, 141 reviews

A view from a window showcases vibrant pink and white flowers in window boxes, framing a serene lake scene. Beyond the flowers, the calm water reflects the gentle colors of the sky, while white Adirondack chairs are positioned on a deck that extends over the pond.

Guesthouse in Plymouth

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.

4.84 out of 5 average rating, 163 reviews

A spacious deck area features a wooden railing overlooking a private lake. The calm water reflects the surrounding greenery, with a dock visible in the distance. Outdoor furniture is arranged nearby, offering a place to relax and enjoy the tranquil setting.

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

Tiny homes in South Yarmouth

A charming cottage is surrounded by lush green trees and shrubs, set within a spacious yard. A gravel pathway leads to the entrance, while a wooden fence provides privacy. Flower boxes add a touch of color to the exterior near the windows.

4.89 out of 5 average rating, 633 reviews

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

4.97 out of 5 average rating, 134 reviews

Two kayaks are stored beside a shed in a natural setting, surrounded by tall grass. A view of the calm water reflects the greenery of the area, while a cozy indoor space showcases a gas fireplace and comfortable furnishings.

Cottage in South Dennis

Local Beach+ Fireplace + Hot Tub Under the *Stars*

Welcome to the Bayside Retreat! Enjoy the real Cape Cod in this Quintessential Beach Rental Featuring: Private hot tub, outdoor patio & high-end sofas in a peaceful backyard 🕊️ 2️⃣ Kayaks- Outdoor Shower- Gas Grill 🔥 Indoor Gas Fireplace ❄️ Mini Splits ✔️Games ✔️Washer/Dryer 📺 55” Sony TV w/ Apps 🛋️ Comfy Furnishings➕Stocked Kitchen Watch the birds, relax out back in peace & privacy or go explore! 📍 Centrally located ❌ NO FEES ⛱️ Year Round Beach Vacation ➡️Bayside_Retreat_Capecod

4.99 out of 5 average rating, 138 reviews

The exterior of a welcoming home is shown, featuring a porch with elegant front doors. Soft lighting illuminates the entryway, while lush greenery and colorful flowers enhance the landscape, providing a warm and inviting entrance.

Apartment in Pembroke

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.

4.84 out of 5 average rating, 279 reviews

A serene view of a clear, spring-fed pond is visible, edged by lush greenery. A wooden dock extends into the water, inviting activities such as swimming or kayaking. Gentle waves ripple on the surface, reflecting the surrounding trees under a clear blue sky.

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, 137 reviews

A wooden dock extends over calm waters, reflecting lights from nearby shorelines. Fireworks burst in vibrant colors above the water, illuminated against a cloudy evening sky. Soft lights from distant buildings create a serene atmosphere, enhancing the tranquil setting of the cove.

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!

Popular amenities for Wareham kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.91 out of 5 average rating, 197 reviews

A charming cottage is framed by a lush garden with vibrant flowers. The front porch features two rocking chairs, inviting relaxation. Soft lighting emanates from inside, through the gothic-style windows, under a welcoming blue roof surrounded by greenery.

Home in Oak Bluffs

impeccable cottage STEPS to downtown OB & beach!

4.97 out of 5 average rating, 39 reviews

The exterior of a traditional Cape Cod home is shown at dusk, featuring large windows that illuminate the cozy living area. Adirondack chairs are positioned on the green lawn, surrounded by bare trees. A separate structure is visible, adding to the charm of the backyard.

Home in Falmouth

Falmouth Summer Fun–Game Barn-Dog Friendly!

A wooden deck extends from the house, featuring a seated area with an Adirondack chair. Expansive views of the ocean and shoreline are visible, framed by low coastal vegetation and a wooden fence. A clear sky with scattered clouds creates a serene backdrop.

4.97 out of 5 average rating, 32 reviews

Oceanfront Home on Cape Cod Bay with Beach Access

4.94 out of 5 average rating, 157 reviews

A spacious living area showcases wooden flooring and high ceilings with exposed beams. Large windows fill the space with natural light, while a cozy sofa and a white coffee table invite relaxation. A kitchen area is visible in the background, providing a functional and open layout.

Home in Vineyard Haven

Vineyard Haven Walk to Ferry

4.98 out of 5 average rating, 46 reviews

A two-story, light purple house stands in a quiet setting, framed by neatly trimmed bushes and blooming white flowers. A brick pathway leads to the front door, which is flanked by two lantern-style lights. Multiple windows provide a bright and open appearance.

Home in Bourne

Bare Feet Retreat

4.86 out of 5 average rating, 154 reviews

The Victorian farmhouse features a wraparound porch with an American flag, providing a welcoming outdoor seating area. The light gray exterior is complemented by white trim and large windows that offer views of the surrounding greenery and spacious lawn.

Home in Buzzards Bay

Waterfront Cape Cod Family Home in Bourne

4.94 out of 5 average rating, 52 reviews

Waterfront Pond House – Private & Peaceful Getaway

4.96 out of 5 average rating, 27 reviews

A sunlit living area features large windows that provide views of the surrounding trees and nearby pond. A cozy circular chair invites relaxation, while a small dining table with black chairs offers a spot for meals. Green plants add a natural touch to the decor.

Home in South Dennis

Nehemiahs Nest: Healing Cape Cod Pond View Cottage

Cottage rentals with a kayak

4.87 out of 5 average rating, 112 reviews

Large floor-to-ceiling windows frame a view of the lake, inviting natural light into the space. The open-concept living area features a comfortable seating arrangement, a dining table, and decorative elements such as floral centerpieces. Wooden beams highlight the high ceilings, enhancing the spacious feel.

Cottage in Falmouth

Spectacular Beach- front home, includes linen

4.94 out of 5 average rating, 124 reviews

The interior space features warm wood paneling with vaulted ceilings and exposed beams. A cozy living area showcases a kitchen bar with seating, while two bedrooms are visible in the background. Natural light streams in through skylights and windows, creating a bright atmosphere.

Cottage in Dennis

Compass Rose Cottage ★ Steps to Flax Pond & Trails

4.94 out of 5 average rating, 49 reviews

A view from a private deck showcases a scenic waterfront with a sandy beach in the distance. Nearby houses frame the scene, and power lines stretch across the sky, emphasizing the tranquil coastal environment.

Cottage in Onset

Payton's Place is your beach get away.

Cottage in South Yarmouth

A view of the waterfront shows a relaxing outdoor seating area featuring a coffee table and comfortable gray sofas. Lush greenery and blooming hydrangeas surround the space, while a clear lake reflects the sky in the background.

5 out of 5 average rating, 240 reviews

SerenityViews | Lakefront | KingBed | Kayaks | FPL

4.92 out of 5 average rating, 133 reviews

A charming Cape cottage is framed by lush greenery, with sections of neatly mulched garden beds featuring flowering plants. An American flag hangs at the entrance, complemented by a stone walkway leading to the front door. The property is bathed in natural sunlight.

Cottage in Dennis Port

Cape Escape-The Perfect Getaway

5 out of 5 average rating, 53 reviews

A sandy beach area is visible in the foreground, adjacent to a calm lake. A cottage is seen in the background, set among trees. Steps lead from the cottage to the beach, enclosed by a fence. Seating areas and kayaks rest nearby.

Cottage in Taunton

Lakefront Cottage w/Private Beach

4.95 out of 5 average rating, 260 reviews

A serene dock extends over calm waters, featuring two Adirondack chairs positioned beside vibrant potted flowers. Lush greenery frames the scene, providing a peaceful backdrop for relaxation. The setting invites guests to unwind and enjoy the tranquility of the freshwater pond.

Cottage in Eastham

The Breeze Overlooking Minister's Pond

4.98 out of 5 average rating, 84 reviews

A wooden staircase leads down through lush greenery to a sandy beach, where the gentle waves meet the shore. The clear blue water stretches into the horizon under a bright sky, inviting visitors to enjoy the coastal atmosphere.

Cottage in Plymouth

Plymouth Cozy Cottage Hot Tub Private Beach

Other vacation rentals with a kayak

5 out of 5 average rating, 26 reviews

A spacious, modern home is set against a vibrant sunset, featuring a large patio area with lounge chairs. Glass doors provide a view of the outdoor hot tub and well-maintained yard, highlighting a welcoming atmosphere for relaxation and enjoyment.

Home in South Yarmouth

Gorgeous Renovation - Boat Dock, Hot Tub, 5 Beds!

5 out of 5 average rating, 3 reviews

A charming gray house is framed by lush greenery and a well-kept yard. A spacious porch is visible at the front, featuring a couple of rocking chairs. The home is complemented by large windows and light-colored vertical siding, under a bright blue sky.

Home in Marion

Marion Village

4.83 out of 5 average rating, 6 reviews

Plymouth's Lakeside Getaway

5 out of 5 average rating, 13 reviews

A cozy exterior view of the house features a gravel driveway leading up to a classic Cape Cod cottage. Lush green lawns are complemented by well-maintained gardens and tall trees. The house is set back from the street, with a spacious fenced-in yard enhancing privacy.

Home in Dennis Port

Cottage Oasis by Lake-Kayaks, Fire Pit & Huge Yard

5 out of 5 average rating, 78 reviews

A sleeping nook features a spacious bed adorned with a colorful floral comforter. Wall decor spells out 'COZY' in decorative letters. A mounted smart TV is positioned above the bed, and natural light illuminates the room through nearby windows.

Home in Falmouth

Waterfront-Kayaks & SUPs-Firepit-Pet OK-Kingbed

4.98 out of 5 average rating, 42 reviews

A spacious, newly constructed home is showcased with a dark blue exterior and white accents. The façade features a prominent front porch with chairs and a large garage. A gravel driveway leads to the entrance, framed by a lush green lawn and trees.

Home in Oak Bluffs

The Blue Lagoon, Oak Bluffs

A spacious outdoor deck features two Adirondack chairs positioned for lake views, offering a relaxing spot to soak in the scenery. A round table sits between the chairs, inviting guests to enjoy drinks while overlooking the calm waters of Wall Pond under a bright blue sky.

4.79 out of 5 average rating, 24 reviews

Waterfront View - Brand New Plymouth Cottage