
Vacation rentals with a kayak in Brewster
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Top-rated kayak rentals in Brewster
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Relaxing Retreat | King Beds * Sauna * Bar Shed
Welcome to Cape Away, your charming family & pet-friendly retreat! Enjoy a fully stocked kitchen, cozy fireplaces, sauna, and outdoor shower. Unwind with dozens of board games, dart board, fire pit, and BBQ. The fully fenced private backyard offers beach gear, a bar shed and lounge area. We are perfectly located just 5–20 minutes from top rated restaurants and beaches, making it your ideal home base. With premium amenities, thoughtful touches it’s the perfect space to escape, explore and relax.

SerenityViews | Lakefront | KingBed | Kayaks | FPL
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!

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.

★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

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!

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

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.

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

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.

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.

* 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.

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.
Popular amenities for Brewster kayak rentals
House rentals with a kayak

Family-Friendly Walk to Beach, Firepit +Autumn Fun

Private beach

Private Lake Beach | Spectacular Views & Amenities

ShoestringBayHouse, waterfront & pool in Cotuit

Cape Cod Bungalow w/ Patio < 1 Mi to Beaches!

2BR/2BA Walk to Beach & Dining

Fall Foliage|Shopping/Dining|Renovated| Fire Pit!

Sunset Point on Long Pond- Large 4BR 3000 sqft
Cottage rentals with a kayak

Waterfront Cape Cottage by Wellfleet’s TOP Beaches

Cape Cottage Escape

1940s Classic Cape Cod Beach Cottage

Historic Lakehouse w/PRIVATE beach, boats and SUPs

Cottage near bay beach- 1 Bd/1Ba

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

Modern Cottage on 6 Acres -Walk to Beach and 6A!

Ocean Front Cottage
Other vacation rentals with a kayak

The Wellfleet Beach House. Sleeps 6

Sunburst Cottage on Long Pond

Large Family Home on Long Pond - Harwich

Cape Cod Escape Pet Friendly Hot Tub Sleeps 10

Seaside Getaway - Harwichport Beachhouse

Kayaks & Double Outdoor Shower! Walk to Long Pond!

Private Waterfront Haven: New! Linens Included!

Adorable Cape Cod Cottage
Quick stats about vacation rentals with a kayak in Brewster

Total vacation rentals
Explore 30 vacation rentals in Brewster

Nightly prices starting at
Brewster vacation rentals start at G$22,974 GYD per night before taxes and fees

Verified guest reviews
Over 1,230 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 10 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!
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