Holiday rentals with a kayak in Brewster

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Top-rated Accommodation with a Kayak in Brewster

Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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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
4.86 out of 5 average rating, 219 reviews

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.

Top Guest favourite
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
4.98 out of 5 average rating, 205 reviews

★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

Guest favourite
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
4.92 out of 5 average rating, 133 reviews

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!

Top Guest favourite
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.
Tiny home in South Yarmouth
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

Top Guest favourite
The spacious kitchen features white cabinetry and a modern layout. A central island with seating is complemented by a dining table nearby. Natural light floods the area through sliding glass doors, enhancing the welcoming ambiance.
Home in Yarmouth
4.95 out of 5 average rating, 184 reviews

Cape Cod Life is Good Rentals

Mid-cape Home Relax in a spacious home that is central to many attractions 8 minutes to the beach, 2 minutes to local golf course and 5 min to Cape Cod Trail. If you are looking for a day trip only 13 min away to Hyannis ferry to Martha's Vineyard/Nantucket or head to visit "P-Town." Endless activities with 3 kayaks available, beach gears, and bikes for family & friends to explore the area. House is located in a quiet neighborhood where you can take a 5 min walk to the cranberry bogs.

Top Guest favourite
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
4.97 out of 5 average rating, 134 reviews

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

Top Guest favourite
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
5 out of 5 average rating, 332 reviews

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

Top Guest favourite
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
4.96 out of 5 average rating, 213 reviews

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.

Top Guest favourite
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
4.95 out of 5 average rating, 258 reviews

The Breeze Overlooking Minister's Pond

The Breeze is a luxurious, romantic cottage by a serene freshwater pond, surrounded by vibrant gardens. Perfect for a peaceful getaway, enjoy kayaking, canoeing, and relaxing on the dock, or explore nearby trails and the Cape Cod Rail Trail with provided bikes. Unwind with evenings by the fire pit, refreshing outdoor showers, and a plush queen bed for ultimate comfort. This private oasis offers tranquility, natural beauty, and 5-star attention to detail for your perfect escape.

Top Guest favourite
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
4.98 out of 5 average rating, 164 reviews

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

Cape Cod - Harwich/Dennis Line - Entire Home, 8 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.

Top Guest favourite
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.
Guesthouse in South Yarmouth
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.

Top Guest favourite
A sandy path meanders through tall grass, leading toward a tranquil sunset in the background. The sun casts a warm glow over the horizon, suggesting the evening calm of the beach area. Soft greens and earthy tones create a peaceful natural setting.
Apartment in East Orleans
4.95 out of 5 average rating, 315 reviews

Cozy Waterfront Apartment, Private Beach Access

Charming living space with nautical decor invites you to unwind off the grid for a few days. There is a window seat for reading, small high top for morning coffee, and all the accessories for a relaxing day at the beach. A five minute drive into town for local shopping and dining. Many scenic trails for walking and biking. Make us your base as you explore Cape Cod’s beautiful shores!

Popular amenities for Brewster kayak rentals

Quick stats about holiday rentals with a kayak in Brewster

  • Total holiday rentals

    Explore 30 holiday rentals in Brewster

  • Nightly prices starting at

    Brewster holiday rentals start at $192 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,230 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Brewster holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Brewster rentals

  • 4.8 Average rating

    Brewster stays are highly rated by guests—averaging 4.8 out of 5!