
Holiday rentals with a kayak in Brewster
Find and book unique kayak rentals on Airbnb
Top-rated Accommodation with a Kayak in Brewster
Guests agree: these holiday homes with a kayak 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.

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.

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

*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. Ask about 20% off weeklong stays in Sept & Oct.

★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

MODERN 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

* 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.

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

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.

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

Cnxl Special 6/27-7/18! Lakefront•Hot Tub•King Bed
✅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

SerenityViews | Waterfront | Kayaks SUP | King Bed
Enjoy our cottage's charm and comfort with panoramic views and abundant sunlight. 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!
Popular amenities for Brewster kayak rentals
Holiday House Rentals with a Kayak

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

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

Cape Cod Life is Good Rentals

Spacious studio on lovely pond in Chatham

Private Beach - 3 bedroom

Cozy Cape Stay! bike path, beaches, water view!

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

Near Beach|Shopping/Dining|Renovated|King Bed
Cottages with a kayak

Compass Rose Cottage ★ Steps to Flax Pond & Trails

The BeachBox

1940s Classic Cape Cod Beach Cottage

Cape Escape-The Perfect Getaway

Cottage near bay beach- 1 Bd/1Ba

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

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

The Breeze Overlooking Minister's Pond
Other holiday rentals with a kayak

West Dennis Beach House - Steps to Beach

Swan Pond Getaway

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

Quiet, Sleeps 6, 2 Full Ba, 5 min Drive to Beach

Waterfront 3 BR Cottage

Cozy ranch with private neighborhood beach

New Home 1 Bedroom and Bath Sleeps 4

Chatham Cottage - Walk to Beach!
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 $98 AUD per night before taxes and fees

Verified guest reviews
Over 1,180 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 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, Wifi and Pool across Brewster rentals

4.8 Average rating
Brewster stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- The Hamptons Holiday rentals
- Rentals with lake access Brewster
- Rentals with a patio Brewster
- Rentals with beach access Brewster
- Rentals with a fire pit Brewster
- Villa rentals Brewster
- Rentals with a hot tub Brewster
- Pet-friendly rentals Brewster
- Rentals with a washing machine and dryer Brewster
- Beachfront rentals Brewster
- House rentals Brewster
- Family-friendly rentals Brewster
- Condo rentals Brewster
- Apartment rentals Brewster
- Cottage rentals Brewster
- Rentals with a fireplace Brewster
- Rentals with pools Brewster
- Rentals with outdoor seating Brewster
- Fitness-friendly rentals Brewster
- Waterfront rentals Brewster
- Rentals with a kayak Barnstable County
- Rentals with a kayak Massachusetts
- Rentals with a kayak United States
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- Craigville Beach
- Duxbury Beach
- Onset Beach
- Sandy Neck Beach
- Coast Guard Beach
- Pinehills Golf Club
- New Silver Beach
- Nauset Beach
- Falmouth Heights Beach
- Saquish Beach
- Lighthouse Beach
- Nickerson State Park
- Skaket Beach
- Cahoon Hollow Beach
- Cape Cod Inflatable Park
- Race Point Beach
- Cape Cod Canal
- Sea Gull Beach
- Town Neck Beach
- Sandwich Glass Museum
- Marconi Beach





