Vacation rentals with a kayak in Brewster

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

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!

4.86 out of 5 average rating, 222 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.

4.96 out of 5 average rating, 139 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 & sofa set in a peaceful backyard 🕊️ 2️⃣ Kayaks- Outdoor Shower- Gas Grill 🔥 Indoor Gas Fireplace ❄️ Mini Splits ✔️Games ✔️Washer/Dryer 📺 55” Sony TV w/ Apps & DirectTV 🛋️ 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

4.98 out of 5 average rating, 210 reviews

A bright bedroom features a spacious bed with colorful blankets and decorative pillows. A variety of sun hats are displayed on the wall, providing a cheerful accent. Natural light enters through the window, illuminating the cozy interior.

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

4.92 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

Enjoy Nantucket Sound beaches, Cape Cod Rail Trail bike path, shops, restaurants and charter boat fishing. Take a scenic drive to Provincetown or stroll seaside festivals. You will love this quintessential Cape cottage for its charm, location, and outdoor space. Spring and fall are beautiful times with everything open without the crowds of the summer. Winter provides a combination of solitude and comfort. Explore the nuances of Cape Cod from this centrally located cottage All are welcome!

Tiny home 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, 635 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

4.88 out of 5 average rating, 169 reviews

The exterior of the house showcases a wooden facade framed by lush greenery. A large wooden deck extends from the back, furnished with chairs, ideal for relaxation. Sunlight filters through the trees, highlighting the serene outdoor space.

Home in Yarmouth Port

* Walk to the beach - Swiss Beach House! *

Walk to the beach! Less than a 1/2 mile (0.7 km)! Perfect spot for paddle boarding. Paddleboards and gas grill (available in summer). Private European - style house. Rustic charm. Laid-back atmosphere. 3 Bedroom, 2.5 bathroom. Comfortably sleeps 6-7, up to 8. Fire pit. Outdoor shower. Farm table for group dining. Fantastic central Cape Cod location. Natural environment. 15 min. to Hyannis for ferries to Nantucket or Martha's Vineyard. Enjoy something unique. Experience the real Cape Cod.

Apartment in Harwich Port

A charming cottage is nestled against sandy dunes, featuring a covered porch with seating. The exterior showcases light grey shingles, and a large circular decorative element is centered on one wall. Beach chairs are positioned near the entrance, inviting relaxation with ocean views.

4.81 out of 5 average rating, 108 reviews

Cape Cod Beachfront 2 bedroom Cottage Harwich

This adorable cottage is reflective of old Cape Cod and is part of a direct beachfront triplex property in the heart of Cape Cod with panoramic views of Pleasant Beach. Although you'll never feel like you need to leave the cottage because of its enviable location and views, it is close to the quaint Harwich village which boasts art and culture, restaurants and dining, shopping and family-friendly activities. This cottage is great for couples, families (with kids), and groups (up to 5).

5 out of 5 average rating, 335 reviews

A wooden outdoor table and benches are positioned on a stone patio, overlooking a serene pond. Lush greenery lines the water's edge, and white flowers in a planter enhance the natural setting. The calm water reflects the surrounding trees and sky.

Home in West Yarmouth

gorgeous waterfront cottage w/4kayaks and 2 SUPs

Small 500 sq ft gem . Quintessential Cape Cod cottage WATERFRONT on big Sandy Pond. Step back in time and enjoy being on Cape Cod in your own Camp. Come enjoy this charming cottage with 2 bedrooms and views of the pond throughout. Kayak, fish and swim from your front door. *1 Paddle Bd *4 kayaks- 4 adult/4 child life vests *Gas Fire-pit *Gas Grill *XL outdoor shower *Quiet lakeside hood *Gorgeous marble counters in the new kitchen *Remote control heating & cooling system *WiFi

4.96 out of 5 average rating, 218 reviews

A tranquil scene captures a couple seated on a dock, surrounded by tall green grasses. The calm water reflects soft hues of pink and blue from the sunset, creating a serene backdrop of trees across the pond.

Home in Dennis Port

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.

4.98 out of 5 average rating, 164 reviews

A game area features a colorful 'Roll and Score' arcade game highlighted by vibrant blue lighting. The background displays a large Boston Red Sox-themed mural, enhancing the playful atmosphere. Beside the arcade game, a shuffleboard table contributes to the entertainment options available.

Home in Harwich

* Game Room, Linens, Quiet St, Central AC/Heat

Cape Cod - Harwich/Dennis Line - Entire Home, 7 Beds (4 Bd/2 Ba), Seasonal Outdoor Shower, Linens Included! Central A/C, Game Room, Cable, Wifi, Pet-Friendly, Near Beaches, Golf, Shopping & Attractions. Great Central Location at CapeVaca. Nearby Beaches: Mayflower, Earle, Pleasant Road, Corporation, West Dennis, Crowe's Pasture, Paines Creek, Harwich, Dennis, Brewster. Message us for early check-in options during the off-seasons. We would love to host you at CapeVaca.

Guesthouse in South Yarmouth

A wooden exterior of the guest apartment is visible, featuring a set of sturdy stairs leading to an upper deck. Vibrant red foliage from a small tree contrasts with the earthy tones of the building. Bright blue skies with scattered clouds provide a serene backdrop.

4.96 out of 5 average rating, 237 reviews

One bedroom guest house on beautiful Cape Cod

Second level guest apartment with one bedroom, bathroom, kitchen, large walk-in closet and living room. Just about everything you need to feel at home. There is A/C in the bedroom and the living area is well vented and has a large ceiling fan. Two golf courses are within 3/4 of a mile, public access beach and boat ramp are within 1 mile. You will also find kayaking, bike trails, walking trails and many other Cape Cod amenities just a short drive away.

Popular amenities for Brewster kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

5 out of 5 average rating, 10 reviews

A cozy outdoor patio is illuminated by soft lighting, creating a welcoming ambiance. A circular fire pit is surrounded by comfortable seating. The nearby entrance offers a glimpse into the home, enhancing the inviting atmosphere in a tranquil evening setting.

Home in West Harwich

Family-Friendly Walk to Beach, Firepit +Autumn Fun

4.99 out of 5 average rating, 90 reviews

A spacious backyard features a circular fire pit surrounded by Adirondack chairs in various colors. In the distance, an inviting in-ground pool is visible, complemented by lush greenery and trees lining the property, creating a serene outdoor setting.

Home in Sandwich

"Cape Escape" luxury home w/pool & beach access.

5 out of 5 average rating, 22 reviews

A charming house is surrounded by lush greenery, featuring a pathway of stone leading to the entrance. Solar panels are mounted on the roof, and large windows allow natural light to fill the space. A small decorative birdbath is visible in the garden area.

Home in Mashpee

Swan nest escape

4.98 out of 5 average rating, 52 reviews

Two white Adirondack chairs are positioned on a sandy beach area by Wequaquet Lake, facing calm waters. A swan glides gracefully in the distance, surrounded by greenery. The serene landscape offers a sense of tranquility, ideal for relaxation.

Home in Barnstable

Private Lake Beach | Spectacular Views & Amenities

4.95 out of 5 average rating, 22 reviews

An aerial view reveals a spacious bay front home surrounded by lush greenery. A large pool is visible in the backyard, with steps leading down to a beach area featuring kayaks. The residence is set in a tranquil, wooded environment.

Home in Cotuit

ShoestringBayHouse, waterfront & pool in Cotuit

4.82 out of 5 average rating, 11 reviews

A cozy game room features a high, wooden-beamed ceiling and ample natural light from large windows. Comfortable bean bags and a sofa provide seating near a coffee table and foosball game. A wall-mounted TV adds entertainment options to this inviting space.

Home in Orleans

Private Beach - 3 bedroom

4.91 out of 5 average rating, 33 reviews

A wooden deck is shown in a private backyard, featuring a dining table surrounded by blue chairs. Potted flowers add color, while tall trees provide shade, creating a serene outdoor space suitable for gatherings.

Home in West Yarmouth

Cape Cod Bungalow w/ Patio < 1 Mi to Beaches!

5 out of 5 average rating, 10 reviews

Home in Yarmouth Port

Packets on the Bay/SUP, Ocean and Marsh Views

Cottage rentals with a kayak

5 out of 5 average rating, 53 reviews

A well-maintained pathway leads to a serene cottage entrance, flanked by lush greenery and landscaped beds. A stone water feature creates a calming ambiance, while lounge chairs are positioned nearby for relaxation. Sunlight filters through the trees, enhancing the tranquil outdoor setting.

Cottage in North Eastham

Cape Cottage Escape

4.89 out of 5 average rating, 18 reviews

The tranquil scene captures a calm body of water reflecting a vibrant sky filled with scattered clouds at sunset. Shades of blue, orange, and yellow are visible, creating a serene atmosphere. The horizon gently blends with the water, inviting a peaceful moment of reflection.

Cottage in Wellfleet

1940s Classic Cape Cod Beach Cottage

4.83 out of 5 average rating, 30 reviews

A sandy beach area is viewed, featuring four white Adirondack chairs arranged to overlook a calm lake. Various boats, including kayaks and a sailboat, are visible on the water. Lush green foliage surrounds the scene, enhancing the natural setting.

Cottage in Barnstable

Historic Lakehouse w/PRIVATE beach, boats and SUPs

4.85 out of 5 average rating, 13 reviews

The exterior of the condo duplex is showcased, featuring a shingle-style façade, a welcoming porch with a white door, and large windows. Lush greenery, including shrubs and a small tree, surrounds the entrance, enhancing the inviting appearance of the property.

Cottage in Brewster

Cottage near bay beach- 1 Bd/1Ba

4.88 out of 5 average rating, 34 reviews

A view from the dock extends across the calm water of Sand Pond, with lush trees lining the opposite shore. The clear blue sky is reflected in the water, creating a tranquil atmosphere. Two wooden posts stand towards the edge of the dock.

Cottage in Harwich

Lakeside Waterfront House in Harwich: 4+beds, 3bth

4.94 out of 5 average rating, 17 reviews

The cottage exterior is showcased, featuring a charming purple façade with black shutters. A landscaped yard with a gravel pathway leads to a private deck area. Surrounding greenery includes trees and shrubs, creating a tranquil outdoor setting.

Cottage in Brewster

Modern Cottage on 6 Acres -Walk to Beach and 6A!

4.9 out of 5 average rating, 52 reviews

A serene view of the ocean at sunset is presented, with soft pink and purple hues reflecting on the calm water. A rocky jetty is visible extending into the water, leading toward the tranquil shoreline.

Cottage in Dennis Port

Ocean Front Cottage (July/Aug Sat-Sat only)

4.95 out of 5 average rating, 261 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

Other vacation rentals with a kayak

5 out of 5 average rating, 26 reviews

A charming Cape-style residence is surrounded by a spacious green lawn, framed by trees. The house features a sloping roof and a brick chimney, with large windows allowing plenty of natural light. A gravel driveway provides ample parking space.

Home in Wellfleet

The Wellfleet Beach House. Sleeps 6

5 out of 5 average rating, 3 reviews

A serene lake view is captured under a clear blue sky, featuring calm waters bordered by lush greenery. A mannequin draped in a handmade garment stands near the water's edge, blending art with the natural landscape.

Home in Dennis Port

Swan Pond Getaway

4.85 out of 5 average rating, 55 reviews

The living room features two comfortable sofas adorned with colorful cushions, situated around a wooden coffee table on a vibrant area rug. Natural light fills the space, highlighting the dining area and fully equipped kitchen visible in the background.

Condo in Brewster

Ocean Edge: 2 bed/2 bath - Pools & Resort Access

5 out of 5 average rating, 17 reviews

The exterior of the cottage features a wrap-around sunroom with large windows, allowing abundant natural light. A gravel pathway leads to the entrance, flanked by a wooden deck and surrounded by lush greenery. A gazebo can be seen in the background, adding to the inviting outdoor space.

Home in Yarmouth Port

Waterfront 3 BR Cottage

5 out of 5 average rating, 58 reviews

The exterior of the apartment is shown, featuring a two-story building with textured wooden siding. The backyard presents a grassy area with seating options, including patio furniture. Access to balconies is visible, along with pink umbrellas and several windows that allow natural light into the units.

Apartment in Centerville

Modern Luxury, Central Location, Bikes & Kayak

5 out of 5 average rating, 87 reviews

An open living area features large glass doors that provide views of the golf course. A comfortable seating arrangement includes a recliner and a sectional sofa. A spiral staircase leads to the loft above, and a mounted television is positioned above a modern fireplace.

Condo in Brewster

Ocean Edge Resort/Pool access/2bedroom-2bath Condo

4.96 out of 5 average rating, 70 reviews

An aerial view captures the layout of the property, featuring two houses connected by a spacious driveway. Lush greenery surrounds the homes, with blooming azaleas in vibrant colors near the entrance. The backyard is expansive and well-maintained, providing a sense of seclusion.

Home in Chatham

2 House Compound, Huge Yard, Game Room, Kayaks