
Holiday rentals with a kayak in Orleans
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Orleans
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

SerenityViews | Waterfront | King Bed | Kayaks SUP
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.

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 Watch the birds, relax out back in peace & privacy or go explore! 📍 Centrally located ❌ NO FEES ⛱️ Year Round Beach Vacation ➡️Bayside_Retreat_Capecod

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!

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

*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. In Sept and Oct, weeks are 20% discounted.

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.

* 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.

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, 7 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 kayak rentals in Orleans
House rentals with a kayak

Hot Tub, Game Room, near mayflower beach

The Wellfleet Beach House. Sleeps 6

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

Large Family Home on Long Pond - Harwich

Sunburst Cottage on Long Pond

Private Lake Beach | Spectacular Views & Amenities

Relax and unwind from holidays at Red Door Retreat

Packets on the Bay/SUP, Ocean and Marsh Views
Cottage rentals with a kayak

★Waterview ★Pet Friendly ★Kayaks ★Trails ★

The BeachBox

1940s Classic Cape Cod Beach Cottage

Historic Lakehouse w/PRIVATE beach, boats and SUPs

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

Beachfront at Days' Cottages! Renovated, Kayaks!

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

Ocean Front Cottage (July/Aug Sat-Sat only)
Other holiday rentals with a kayak

Family-Friendly Walk to Beach, Firepit +Autumn Fun

Swan Pond Getaway

The Lux shire

Ocean Edge: 2 bed/2 bath - Pools & Resort Access

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

Waterfront-Private Deck-Kitchen- on Commercial Apt

Waterfront 3 BR Cottage

Ocean Edge Resort/Pool access/2bedroom-2bath Condo
Quick stats about holiday rentals with a kayak in Orleans

Total holiday rentals
Explore 30 holiday rentals in Orleans

Nightly prices starting at
Orleans holiday rentals start at £97 per night before taxes and fees

Verified guest reviews
Over 1,150 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Orleans holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Orleans rentals

4.9 Average rating
Orleans stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with a kayak Barnstable County
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- Rentals with a kayak United States
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Onset Beach
- White Horse Beach
- Coast Guard Beach
- Pinehills Golf Club
- Chapin Memorial Beach
- Inman Road Beach
- Nauset Beach
- Lighthouse Beach
- Town Neck Beach
- Ellis Landing Beach
- Linnell Landing Beach
- New Silver Beach
- Peggotty
- Nickerson State Park
- Falmouth Beach
- Cape Cod Inflatable Park
- Scusset Beach
- Forest Beach




