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Holiday rentals with a kayak in Brewster

Find and book unique kayak rentals on Airbnb

Quick stats about holiday rentals with a kayak in Brewster

  • Total holiday rentals

    Explore 40 holiday rentals in Brewster

  • Nightly prices starting at

    Brewster holiday rentals start at $179 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,660 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Brewster holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Brewster rentals

  • 4.8 Average rating

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

Top-rated rentals with kayak in Brewster

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

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Guest favourite
Cottage in Harwich Port

2BR Directly on Pleasant Beach – 30 Steps to Ocean

You are not near the beach- You are on it! Only 30 steps from your door to the ocean! Fall asleep to waves. This is a true beachfront cottage located directly on Pleasant Beach. Drink your morning coffee watching the tide roll in. 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. You'll never feel like you need to leave the cottage but it is close to the quaint Harwich village.

4.82 out of 5 average rating, 129 reviews
Top guest favourite
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.
Apartment in Brewster

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

Recently renovated end unit townhouse located in the heart of The OE Villages. Beautiful views towards the golf course, and southern exposure with lots of natural light, A/C, W/D and private patio with Weber grill and outdoor furniture. Sports Membership so Guest passes are available for purchase at Linx for use of pools, hot tubs and gyms. Additional costs for use of courts may apply. Bike rail trail, Ice cream store, great restaurants, coffee, beaches and Kayak/Bike rentals are all close by.

5.0 out of 5 average rating, 105 reviews
Guest favourite
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.

4.87 out of 5 average rating, 246 reviews
Top guest favourite
An outdoor seating area is presented with plush, striped furniture and a large firepit at the center. A bright turquoise umbrella provides shade, while the tranquil waterfront view showcases shimmering water and greenery. Potted flowers add a touch of color to the serene setting.
Home in Harwich

Waterfront★ Pvt Beach ★ On Bike Path ★Bikes★Kayaks

*Beautifully decorated waterfront cottage w/ bluestone patio- private beach 🏡 * Directly on Cape Cod Rail Trail Bike Path 🚲 *Sunsets from the couch 🌅 *Central A/C ❄️ *Private sandy beach on crystal clear lake 🏖️ *2 Kayaks, 6 Bikes & 2 SUP’s incl- 🛶 🚲 saving $400-$600 in rental fees *6min drive to Bay Beach🏝️ *Large waterfront LR w/65" Frame TV 📺 * Beds-1 king, 1 queen, 2 twins 🛌 *Gas Fire-table 🔥 *Outdoor shower 🚿 *Woodburning FPL in LR * Pet friendly-$30/nt 🐶 😺

4.96 out of 5 average rating, 85 reviews
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

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 🛁New Bathroom 🕊️Relax out back in peace & privacy or go explore! 📍 Centrally located ❌NO FEES ⛱️ Year Round Beach Vacation ➡️Bayside_Retreat_Capecod

4.96 out of 5 average rating, 169 reviews
Top guest favourite
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

4.98 out of 5 average rating, 250 reviews
Top guest favourite
A wooden sign is displayed, featuring a welcoming message that reads 'welcome to Cape Cod.' The text is artistically styled, with blue waves and a small sailing boat illustrated underneath.
Guest suite in Brewster

Sheep Pond Get-Away

The AirbNB Studio Space is Private w/ its own separate entrance & exit. Our home is set in the 'Sheep Pond' area. We are walking distance to Sheep Pond to kayak & swim. We have kayaks, paddleboards, beachchairs, & towels for your use. A backyard w/ your own picnic table, seating area, & hammock. An outdoor shower ! Minutes away from bay & oceanside beaches, biking, hiking & Nickerson State Park. 40 mins from Provincetown; & surrounded by quaint Route 6a, restaurants & shopping !

4.97 out of 5 average rating, 425 reviews
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 Yarmouth

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

4.89 out of 5 average rating, 680 reviews
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

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

5.0 out of 5 average rating, 368 reviews
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

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.

4.96 out of 5 average rating, 240 reviews
Top guest favourite
Home in Yarmouth Port

Sauna · Fireplace · Waterfront · 2 Kings · DogsYes

☆ Waterfront, located on private saltwater beach (with central location) ☆ Sauna (year-round) ☆ Cozy fireplace (electric) ☆ 3-season patio ☆ 1% donated to Cape nonprofits ☆ 2 Kayaks & 2 Paddle boards ☆ Outdoor fire pit & charcoal grill ☆ Ample workspace ☆ Dog Friendly ☆ Washer/dryer ☆ 2 King Beds with 50" TVs in bedrooms ☆ Outdoor shower (open May through fall) ☆ Beach chairs provided ☆ Linens, all towels provided ☆ 10min from bay or ocean beach ☆ 15min MV & Nantucket ferries

4.99 out of 5 average rating, 133 reviews
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

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

Cape Cod - Harwich/Dennis Line - Entire Home, 6 Beds + Futon (4 Bd/2 Ba), Includes 2 King Beds, 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.

4.98 out of 5 average rating, 178 reviews

Popular amenities for kayak rentals in Brewster

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a kayak

Guest favourite
Home in Yarmouth Port

* Walk to the beach - Swiss Beach House! *

4.88 out of 5 average rating, 192 reviews
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

Cape Cod Life is Good Rentals

4.96 out of 5 average rating, 224 reviews
Guest favourite
Home in Brewster

3BR Pond Views | Private Beach & Kayaks

5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in South Dennis

Dog-Friendly Home w Pond Access and Canoe, for 7

4.86 out of 5 average rating, 7 reviews
Top guest favourite
A spacious living area is presented with large windows offering panoramic views of the lake. A comfortable sectional sofa and inviting armchairs surround a coffee table, with light wood flooring and a neutral rug enhancing the relaxed ambiance. The fireplace is styled neatly, with decorative elements arranged nearby.
Home in Dennis Port

Stunning Waterfront Home w/ Hot Tub, Deck & Office

4.97 out of 5 average rating, 39 reviews
Top guest favourite
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

4.96 out of 5 average rating, 73 reviews
Superhost
The exterior of the house showcases a wood-shingled façade and a red door, providing a contrasting accent. A spacious deck holds a set of five outdoor chairs around a small table, ideal for al fresco dining. Clear skies and scattered clouds form the backdrop.
Home in Brewster

Cape Cod Escape Pet Friendly Hot Tub Sleeps 10

4.76 out of 5 average rating, 54 reviews
Top guest favourite
Home in Dennis Port

Luxury Waterfront - Hot Tub, Deck & Waterviews

5.0 out of 5 average rating, 12 reviews

Cottage rentals with a kayak

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

Cape Escape-The Perfect Getaway

4.93 out of 5 average rating, 138 reviews
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

The Breeze Overlooking Minister's Pond

4.96 out of 5 average rating, 278 reviews
Guest favourite
A serene sunset displays vibrant hues of orange, pink, and purple across the water. Soft clouds reflect the colorful sky above a calm bay, creating a tranquil atmosphere. The smooth shoreline is visible in the foreground, leading to the water's edge.
Cottage in Brewster

Amazing Sunsets

4.96 out of 5 average rating, 24 reviews
Top guest favourite
A serene view from a wooden dock extends towards a calm lake, framed by lush greenery. Two kayaks rest nearby, while a small floating platform is visible on the water. The clear sky and gentle ripples on the lake enhance the tranquil atmosphere.
Cottage in Harwich

Sand Pond Perfection

4.98 out of 5 average rating, 43 reviews
Top guest favourite
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

4.91 out of 5 average rating, 43 reviews
Top guest favourite
A view from the interior of the cottage showcases large windows framing the serene water scene outside. A wooden dining table with chairs is visible, along with a desk area that faces the water. Exposed beams line the ceiling, enhancing the rustic design.
Cottage in Barnstable

Serenity Point Waterfront Cottage

4.99 out of 5 average rating, 72 reviews
Guest favourite
A landscaped yard features a stone fire pit surrounded by curved seating. In the background, a view of the ocean is visible beyond the grassy area. The sky is clear, indicating a sunny day, while a vehicle can be seen parked across the street.
Cottage in Dennis Port

Across from Glendon Beach-Ocean View and Fire Pit!

5.0 out of 5 average rating, 22 reviews
Top guest favourite
Cottage in Barnstable

Storybook Cottage | Historic Charm & Lake Access

5.0 out of 5 average rating, 24 reviews

Other holiday rentals with a kayak

Guest favourite
Apartment in Brewster

Resort Pools & Golf Views · Walk to Bay Beaches

4.87 out of 5 average rating, 77 reviews
Guest favourite
Cabin in Orleans

On Bakers Pond, an Upscale Cabin.

5.0 out of 5 average rating, 21 reviews
Guest favourite
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

4.95 out of 5 average rating, 77 reviews
Guest favourite
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 West Yarmouth

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

4.94 out of 5 average rating, 34 reviews
Guest favourite
Home in West Harwich

The Cape Codder: Large Yard, Steps to Town & Beach

4.95 out of 5 average rating, 20 reviews
Guest favourite
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

4.97 out of 5 average rating, 97 reviews
Top guest favourite
A charming antique Cape Cod home is framed by a white picket fence and surrounded by lush greenery. The exterior features a gray wood shingle facade and multiple windows. Two red adirondack chairs are positioned on the front porch, inviting relaxation amidst the serene garden.
Home in Orleans

1850 Orleans Antique Home with Path to Arey’s Pond

4.96 out of 5 average rating, 53 reviews
Guest favourite
An aerial view captures the home nestled amidst lush greenery, with the winding waterway and marshland visible in the background. The roofline and outdoor pathways are highlighted, showcasing the serene natural surroundings that enhance the retreat experience.
Home in Eastham

Waterfront Oasis - Kayak Access & Stunning Views!

4.9 out of 5 average rating, 29 reviews

Destinations to explore