
Vacation rentals with a kayak in Brewster
Find and book unique kayak rentals on Airbnb
Quick stats about vacation rentals with a kayak in Brewster

Total vacation rentals
Explore 40 vacation rentals in Brewster

Nightly prices starting at
Brewster vacation rentals start at ﺩ.ﺇ 514 per night before taxes and fees

Verified guest reviews
Over 1,660 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Brewster vacation rentals include wi-fi 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 kayak rentals in Brewster
Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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.
Outdoor spacesValueHeating
4.82 out of 5 average rating, 129 reviews
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.
LocationValueBeach
5.0 out of 5 average rating, 104 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.
LocationValueHiking
4.87 out of 5 average rating, 245 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 & 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
LocationOutdoor spacesHospitality
4.96 out of 5 average rating, 169 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
Outdoor spacesLocationFamily
4.98 out of 5 average rating, 249 reviews
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 !
LocationValueBeach
4.97 out of 5 average rating, 423 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
Outdoor spacesValueGetting around
5.0 out of 5 average rating, 368 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.
ValueOutdoor spacesParks
4.96 out of 5 average rating, 239 reviews
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
ValueLocationBathroom
4.99 out of 5 average rating, 133 reviews
Waterfront•Hot Tub • Kayaks/SUP's • King Bed •Dock
✅All linens provided & beds made ✅ King bed / Queen / Twin over Full bunk ✔ Direct lake access = natural cold plunge ✔ Private waterfront hot tub (open year-round) ✔ 1 King bed + Queen + twin over bunk room ✔ Dock for swimming & fishing ✔ 2 kayaks + 2 SUPs ✔ Gas fireplace ✔ Large waterfront dining room ✔ Fully stocked kitchen w/ marble counters ✔ Patio + fire pit + deck dining ✔ Washer/Dryer ✔ Dog friendly ($30/day) ✔ All linens & towels provided Locally managed
LocationValueQuiet
4.94 out of 5 average rating, 271 reviews
* 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.
ValueOutdoor spacesCheck-in
4.98 out of 5 average rating, 177 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!
LocationOutdoor spacesBathroom
4.95 out of 5 average rating, 340 reviewsPopular amenities for Brewster kayak rentals
House rentals with a kayak

* Walk to the beach - Swiss Beach House! *
ValueLocationHiking
4.87 out of 5 average rating, 191 reviews
Cape Cod Life is Good Rentals
LocationOutdoor spacesAccuracy
4.96 out of 5 average rating, 223 reviews
Cape Fever - 161 Berry Ave
ValueOutdoor spacesBackyard
4.82 out of 5 average rating, 101 reviews
3BR Pond Views | Private Beach & Kayaks
LocationOutdoor spacesIndoor spaces
5.0 out of 5 average rating, 7 reviews
Dog-Friendly Home w Pond Access and Canoe, for 7
LocationValueDecor
4.86 out of 5 average rating, 7 reviews
Stunning Waterfront Home w/ Hot Tub, Deck & Office
Outdoor spacesLocationDecor
4.97 out of 5 average rating, 39 reviews
Cape Cod Escape Pet Friendly Hot Tub Sleeps 10
LocationOutdoor spacesBeach
4.75 out of 5 average rating, 53 reviews
Nehemiahs Nest: Healing Cape Cod Pond View Cottage
LocationOutdoor spacesBathroom
4.96 out of 5 average rating, 71 reviewsCottage rentals with a kayak

MODERN COTTAGE W/ BIKES, PADDLE BOARDS & KAYAKS
ValueLocationLayout
4.92 out of 5 average rating, 543 reviews
Cape Escape-The Perfect Getaway
LocationValueKitchen
4.93 out of 5 average rating, 138 reviews
The Breeze Overlooking Minister's Pond
LocationOutdoor spacesSleep quality
4.96 out of 5 average rating, 278 reviews
Amazing Sunsets
Outdoor spacesLocationFamily
4.96 out of 5 average rating, 24 reviews
Sand Pond Perfection
LocationOutdoor spacesAccuracy
4.98 out of 5 average rating, 40 reviews
Lakeside Waterfront House in Harwich: 4+beds, 3bth
ValueOutdoor spacesNearby
4.91 out of 5 average rating, 43 reviews
Serenity Point Waterfront (Now Booking for Fall)
LocationOutdoor spacesAccuracy
4.99 out of 5 average rating, 70 reviews
Across from Glendon Beach-Ocean View and Fire Pit!
Outdoor spacesLocationCleanliness
5.0 out of 5 average rating, 22 reviewsOther vacation rentals with a kayak

Resort Pools & Golf Views · Walk to Bay Beaches
Outdoor spacesLocationAmenities
4.87 out of 5 average rating, 76 reviews
On Bakers Pond, an Upscale Cabin.
Outdoor spacesLocationQuiet
5.0 out of 5 average rating, 21 reviews
Lake House with Private Lake Access
LocationOutdoor spacesKitchen
4.86 out of 5 average rating, 14 reviews
2 House Compound, Huge Yard, Game Room, Kayaks
Outdoor spacesLocationWifi
4.95 out of 5 average rating, 77 reviews
Waterfront Oasis - Kayak Access & Stunning Views!
LocationOutdoor spacesAccess
4.9 out of 5 average rating, 29 reviews
Cottage at Turtle Crossing
Outdoor spacesLocationSleep quality
4.99 out of 5 average rating, 82 reviews
Beautiful lakefront vacation property in Mashpee
ValueOutdoor spacesKitchen
4.96 out of 5 average rating, 97 reviews
Summer House
LocationOutdoor spacesCondition
4.99 out of 5 average rating, 73 reviewsDestinations to explore
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