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Holiday rentals with a kayak in Orleans

Find and book unique kayak rentals on Airbnb

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 €149 per night before taxes and fees

  • Verified guest reviews

    Over 1,240 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 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!

Top-rated rentals with kayak in Orleans

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.

Outdoor spacesLocationHeating

4.82 out of 5 average rating, 129 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.

LocationValueFamily

4.87 out of 5 average rating, 246 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.

Outdoor spacesLocationQuiet

5.0 out of 5 average rating, 105 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

LocationValueAccuracy

4.96 out of 5 average rating, 170 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

Outdoor spacesLocationCleanliness

4.98 out of 5 average rating, 250 reviews
Top guest favourite
Home in Sandwich

"Cape Escape" luxury home w/pool & beach access.

Welcome to the Cape Escape! Enjoy views of Spectacle Pond from the 70 ft. deck of this recently renovated 5 bed/3 bath spacious home meeting all your needs! Relax by the in-ground pool in the private enclosed yard. Enjoy nights around the fire-pit. Directly across the driveway you can enjoy kayaking, sunbathing & swimming at the neighborhood beach. Within 6 miles of the home you will find the historic Sandwich boardwalk, Ocean beaches, Cape Cod Canal and more! Perfect for family gatherings!

ValueOutdoor spacesFamily

4.99 out of 5 average rating, 103 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 !

ValueLocationDecor

4.97 out of 5 average rating, 425 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

LocationValueBathroom

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.

ValueOutdoor spacesBeach

4.96 out of 5 average rating, 240 reviews
Top guest favourite
A calm freshwater pond is surrounded by lush greenery and tall trees. A float is visible on the water, providing a serene spot for relaxation. Lilypads are scattered across the surface, reflecting the clear blue sky.
Guest suite in Chatham

Spacious studio on lovely pond in Chatham

Enjoy this spacious studio apartment on a gorgeous, clean private pond. Separate entrance and lots of privacy; direct access to private freshwater beach, with a lovely float. Kayaks are available so you can enjoy the twin ponds. Note: no actual kitchen, but there is a wet bar with a Keurig and fridge to help start each day nicely. The studio has a King-size bed. In addition to the freshwater pond on the property, numerous bay and ocean beaches are just a 5 minute drive away

ValueLocationFamily

4.91 out of 5 average rating, 107 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

ValueOutdoor spacesHospitality

4.99 out of 5 average rating, 133 reviews
Top guest favourite
A serene waterfront view showcases a tranquil pond surrounded by lush greenery. Two kayaks are visible on the grassy area, while the deck features a wooden table with white chairs, inviting relaxation and outdoor dining.
Cottage in Yarmouth

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!

Outdoor spacesValueAccuracy

4.99 out of 5 average rating, 261 reviews

Popular amenities for kayak rentals in Orleans

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a kayak

Top guest favourite
A waterfront hot tub is set against a natural backdrop of trees and calm waters. Inside, a dining area features a large window with views of the lake. A cozy living room displays comfortable seating, while an outdoor patio has seating for relaxation and enjoying the scenery.
Home in South Yarmouth

Waterfront•Hot Tub • Kayaks/SUP's • King Bed •Dock

ValueOutdoor spacesHot tub

4.94 out of 5 average rating, 271 reviews
Guest favourite
Home in Yarmouth Port

* Walk to the beach - Swiss Beach House! *

ValueOutdoor spacesAir conditioning

4.88 out of 5 average rating, 192 reviews
Guest favourite
An aerial view showcases a large estate set against a tranquil bay. The property features a sprawling lawn, with a red building juxtaposed against a neighboring white house and lush trees. The calm waters reflect the clear blue sky, enhancing the serene ambiance of the area.
Home in Orleans

Private beach

LocationOutdoor spacesAccess

4.88 out of 5 average rating, 50 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

LocationOutdoor spacesPets

4.96 out of 5 average rating, 53 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

Outdoor spacesLocationQuiet

4.97 out of 5 average rating, 39 reviews
Top guest favourite
A cozy cottage exterior is presented, featuring a shingled façade with blue trim around the windows and doors. An American flag is displayed prominently. A wooden deck leads to the entrance, surrounded by neatly arranged flower beds and a large planter situated in the foreground.
Home in Eastham

Cottage at Turtle Crossing

Outdoor spacesLocationBeach

4.99 out of 5 average rating, 82 reviews
Top guest favourite
Home in Dennis Port

Luxury Waterfront - Hot Tub, Deck & Waterviews

LocationOutdoor spacesIndoor spaces

5.0 out of 5 average rating, 12 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

Outdoor spacesLocationBiking

4.95 out of 5 average rating, 77 reviews

Cottage rentals with a kayak

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

LocationOutdoor spacesHospitality

4.96 out of 5 average rating, 278 reviews
Top guest favourite
The interior space features warm wood paneling with vaulted ceilings and exposed beams. A cozy living area showcases a kitchen bar with seating, while two bedrooms are visible in the background. Natural light streams in through skylights and windows, creating a bright atmosphere.
Cottage in Dennis

Compass Rose Cottage ★ Steps to Flax Pond & Trails

Outdoor spacesValueWifi

4.95 out of 5 average rating, 136 reviews
Guest favourite
A cozy living area is highlighted by a navy blue sofa adorned with decorative pillows. The light wood floor complements the bright blue walls, while a flat-screen TV and a coffee table with remote sit within the space. Natural light filters through large glass doors, overlooking a private patio.
Cottage in Yarmouth

MODERN COTTAGE W/ BIKES, PADDLE BOARDS & KAYAKS

LocationValueWifi

4.92 out of 5 average rating, 545 reviews
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

Outdoor spacesValueFamily

4.92 out of 5 average rating, 139 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

LocationValueKitchen

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

Outdoor spacesLocationParks

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

LocationOutdoor spacesCheckout

4.99 out of 5 average rating, 72 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

LocationOutdoor spacesHospitality

4.96 out of 5 average rating, 24 reviews

Other holiday rentals with a kayak

Guest favourite
Cabin in Orleans

On Bakers Pond, an Upscale Cabin.

LocationOutdoor spacesHiking

5.0 out of 5 average rating, 21 reviews
Top guest favourite
A fire pit area features six sturdy blue Adirondack chairs arranged around a circular stone fire pit, overlooking a serene waterfront view. Lush greenery surrounds the area, with the calm water of Long Pond visible in the background.
Home in Yarmouth

Sunburst Cottage on Long Pond

ValueOutdoor spacesNearby

4.99 out of 5 average rating, 93 reviews
Guest favourite
A spacious outdoor patio features a cozy seating area with comfortable cushions, surrounded by lush trees. A scenic view of the peaceful lake is visible in the distance, framed by the greenery. The inviting stone surface complements the natural surroundings.
Home in Harwich

Lake House with Private Lake Access

ValueOutdoor spacesBack garden

4.86 out of 5 average rating, 14 reviews
Guest favourite
Home in Brewster

3BR Pond Views | Private Beach & Kayaks

LocationOutdoor spacesBack garden

5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in West Harwich

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

LocationOutdoor spacesBathroom

4.95 out of 5 average rating, 20 reviews
Top guest favourite
A serene waterfront view presents a vibrant sunset with colorful clouds reflecting on the calm water. Several outdoor chairs are positioned on a sandy area, offering a space to relax. The landscape is framed by trees, enhancing the natural surroundings.
Home in Mashpee

Beautiful lakefront vacation property in Mashpee

LocationOutdoor spacesAccess

4.96 out of 5 average rating, 97 reviews
Top guest favourite
A wooden boardwalk extends towards the calm ocean, framed by a sandy beach and gentle blue waves. Smooth rocks accompany the path, and the sky is clear with wispy clouds, creating a serene coastal scene.
Home in Plymouth

The Quarterdeck | Oceanfront Fun for All Ages

LocationOutdoor spacesBack garden

5.0 out of 5 average rating, 63 reviews
Top guest favourite
The exterior of the cottage features a wrap-around sunroom with large windows, allowing abundant natural light. A gravel pathway leads to the entrance, flanked by a wooden deck and surrounded by lush greenery. A gazebo can be seen in the background, adding to the inviting outdoor space.
Home in Yarmouth Port

Waterfront 3 BR Cottage with Dock

Outdoor spacesLocationDecor

5.0 out of 5 average rating, 26 reviews

Destinations to explore