Holiday rentals with a kayak in Brewster

Cottage in South Yarmouth

A serene waterfront view showcases a tranquil pond surrounded by lush greenery. Two kayaks are visible on the grassy area, while the deck features a wooden table with white chairs, inviting relaxation and outdoor dining.

5 out of 5 average rating, 241 reviews

SerenityViews | Waterfront | King Bed | 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!

4.87 out of 5 average rating, 226 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, 140 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, 213 reviews

A sandy beach is visible in the foreground, leading to a calm body of water. The surface of the lake reflects a bright blue sky filled with white clouds, while lush greenery lines the shore in the background.

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

4.93 out of 5 average rating, 134 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, 636 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

Guest suite in West Dennis

The exterior of the Victorian home showcases a charming entrance, featuring a central glass door framed by large windows. Vibrant greenery and blooming plants surround the entrance, providing a welcoming atmosphere. A slate pathway leads up to the steps, offering easy access to the porch.

4.94 out of 5 average rating, 155 reviews

*Bass River Victorian Escape* Central A/C*WiFi

Get away from it all. This beautiful, Victorian semi-detached home is part of a former sea captain’s house. Refurbished to a high standard, it is light and spacious with 2 bedrooms and 1.5 bathrooms, fully equipped kitchen, and a 3-season porch with its own entrance. The open floor plan, central A/C, W/D in basement, WiFi, smart TV, outdoor BBQ, and shelves filled with books and games for all ages will make your family vacation that much better. In Sept and Oct, weeks are 20% discounted.

4.88 out of 5 average rating, 170 reviews

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.

4.81 out of 5 average rating, 110 reviews

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.

Flat in Harwich Port

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, 336 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, 165 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.

Popular amenities for kayak rentals in Brewster

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

5 out of 5 average rating, 18 reviews

Home in East Dennis

Hot Tub, Game Room, near mayflower beach

A fire pit area features six sturdy blue Adirondack chairs arranged around a circular stone fire pit, overlooking a serene waterfront view. Lush greenery surrounds the area, with the calm water of Long Pond visible in the background.

5 out of 5 average rating, 72 reviews

Sunburst Cottage on Long Pond

5 out of 5 average rating, 25 reviews

A spacious living area features high ceilings and large windows, creating an open atmosphere. A comfortable arrangement of sofas and armchairs provides ample seating. A fireplace with a decorative mantel is situated against a soft blue wall, complemented by a natural woven coffee table.

Home in Chatham

Relax and unwind from holidays at Red Door Retreat

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

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

4.86 out of 5 average rating, 22 reviews

Home in Chatham

Cheerful 2 bedroom home walk to town location.

A three-story home features a shingled exterior with a red front door. Colorful flowers line the walkway, leading to the entrance. Large windows are adorned with flower boxes, and trees provide greenery around the property.

4.97 out of 5 average rating, 33 reviews

Kayaks & Double Outdoor Shower! Walk to Long Pond!

4.97 out of 5 average rating, 88 reviews

A charming cottage is seen from the front, featuring natural wood siding and a blue door. Well-maintained shrubs and blooming azaleas accentuate the entrance, while a stone pathway leads to the door, framed by a grassy area and trees in the background.

Home in Chatham

Serene Chatham cottage minutes from beach

Cottage rentals with a kayak

4.94 out of 5 average rating, 125 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

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

The BeachBox

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

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

4.8 out of 5 average rating, 15 reviews

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

4.9 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 holiday rentals with a kayak

4.9 out of 5 average rating, 60 reviews

A coastal cottage is shown, featuring a grey shingle exterior and a spacious front porch. An American flag hangs prominently on the facade. The sandy road leads to the entrance, with neighboring houses visible in the background.

Home in West Dennis

West Dennis Beach House - Steps to Beach

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

4.97 out of 5 average rating, 37 reviews

The classic residence features a sandy-colored exterior with a peaked roof and prominent chimney. A well-maintained lawn surrounds the entrance, which includes a porch with seating. Two garages are visible, and an American flag adds a touch of character to the welcoming facade.

Home in Harwich

Large Family Home on Long Pond - Harwich

5 out of 5 average rating, 18 reviews

Large Mid-Cape 5 BR- 3 Bath Home A/C, 2mi to beach

4.94 out of 5 average rating, 83 reviews

A bright living area features a beige sofa adorned with yellow and striped cushions. A glass coffee table sits in front, with a blue decorative bowl at the center. A large mirror and framed artwork accentuate the walls, while natural light filters through the windows.

Home in Dennis

Dennis Getaway & Chill

A spacious living area is presented with a large white sectional sofa, arranged around a wooden coffee table. Natural light enters through the large window, which is framed by light curtains, revealing a view of greenery outside. A relaxed atmosphere is created by the warm tones of the woven decor.

4.95 out of 5 average rating, 37 reviews

Cape Cod Retreat

The living area features a cozy couch facing a modern fireplace, bordered by light-colored shiplap walls. A wooden coffee table rests atop a natural fiber rug, while nautical decor, including a ship's wheel, adorns the wall above. A glimpse of the kitchen is visible in the background.

4.97 out of 5 average rating, 35 reviews

3bdrm, 2miles 2 beach, kayaks, AC, firetable, pond