Holiday rentals with a kayak in Eastham

5 out of 5 average rating, 176 reviews

An outdoor dining setting features a table with a plate of salad and wine glasses, accompanied by a bottle of white wine. In the background, a charming shed displays ‘Cape Away’ signage, surrounded by well-maintained greenery and a cozy lounge area.

Home in South Yarmouth

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.

Cottage in South Yarmouth

A view of the waterfront shows a relaxing outdoor seating area featuring a coffee table and comfortable gray sofas. Lush greenery and blooming hydrangeas surround the space, while a clear lake reflects the sky in the background.

5 out of 5 average rating, 240 reviews

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!

4.79 out of 5 average rating, 192 reviews

A calm waterway reflects soft pastel colors during sunrise, with silhouettes of boats anchored in the distance. Gentle grasses line the foreground, and the tranquil landscape is framed by hills on the horizon, offering a serene morning view.

Guest suite in Pocasset

Rustic Beach Cottage

The salty air will instantly wash all your cares away. This rustic charming Cape get away is steps away from a quaint quiet picturesque beach. Simply relax in the comfortable surrounds in this fully furnished 1 bedroom Cottage apartment with all of your basic needs including WiFi, Smart TV, A/C, and a deck complete with gas grill and outdoor furniture offering you plenty of living space inside and out. Close to the bike paths, Cape Cod Canal, great restaurants, hiking, ferry and much much more!

4.87 out of 5 average rating, 218 reviews

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.

4.92 out of 5 average rating, 132 reviews

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

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!

4.94 out of 5 average rating, 139 reviews

A view from a window showcases vibrant pink and white flowers in window boxes, framing a serene lake scene. Beyond the flowers, the calm water reflects the gentle colors of the sky, while white Adirondack chairs are positioned on a deck that extends over the pond.

Guest house in Plymouth

Charming Pond-Front Boathouse

Charming antique boat house located directly on Long Pond. Quiet, peaceful accommodations with 180 views. Watch the American Bald Eagles and Osprey search for fish at dusk from your private deck that reaches out over the pond. Long Pond is full recreation, two kayaks and a canoe are available. Hiking, bicycling, golfing, fishing, swimming, boating, snorkeling, sunbathing, and napping are just a few of the activities that can be enjoyed in the quaint, semi-private, pond-front accommodation.

Tiny home in South Yarmouth

A charming cottage is surrounded by lush green trees and shrubs, set within a spacious yard. A gravel pathway leads to the entrance, while a wooden fence provides privacy. Flower boxes add a touch of color to the exterior near the windows.

4.89 out of 5 average rating, 633 reviews

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

4.97 out of 5 average rating, 133 reviews

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 & 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

5 out of 5 average rating, 332 reviews

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

4.96 out of 5 average rating, 213 reviews

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.

4.95 out of 5 average rating, 256 reviews

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

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.

4.95 out of 5 average rating, 312 reviews

A sandy path meanders through tall grass, leading toward a tranquil sunset in the background. The sun casts a warm glow over the horizon, suggesting the evening calm of the beach area. Soft greens and earthy tones create a peaceful natural setting.

Flat in East Orleans

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!

Popular amenities for kayak rentals in Eastham

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

5 out of 5 average rating, 26 reviews

A charming Cape-style residence is surrounded by a spacious green lawn, framed by trees. The house features a sloping roof and a brick chimney, with large windows allowing plenty of natural light. A gravel driveway provides ample parking space.

Home in Wellfleet

The Wellfleet Beach House. Sleeps 6

4.88 out of 5 average rating, 169 reviews

The exterior of the house showcases a wooden facade framed by lush greenery. A large wooden deck extends from the back, furnished with chairs, ideal for relaxation. Sunlight filters through the trees, highlighting the serene outdoor space.

Home in Yarmouth Port

* Walk to the beach - Swiss Beach House! *

4.91 out of 5 average rating, 196 reviews

A charming cottage is framed by a lush garden with vibrant flowers. The front porch features two rocking chairs, inviting relaxation. Soft lighting emanates from inside, through the gothic-style windows, under a welcoming blue roof surrounded by greenery.

Home in Oak Bluffs

impeccable cottage STEPS to downtown OB & beach!

4.97 out of 5 average rating, 38 reviews

The exterior of a traditional Cape Cod home is shown at dusk, featuring large windows that illuminate the cozy living area. Adirondack chairs are positioned on the green lawn, surrounded by bare trees. A separate structure is visible, adding to the charm of the backyard.

Home in Falmouth

Falmouth Summer Fun–Game Barn-Dog Friendly!

5 out of 5 average rating, 18 reviews

A spacious wooden deck overlooks Jenkins Pond, featuring a circular dining table surrounded by six green metal chairs. An umbrella stands in the center, providing shade. The serene lake view is framed by trees, enhancing the tranquil outdoor setting.

Home in Falmouth

Lake Shore Cottage - Waterfront with Beach Access

5 out of 5 average rating, 87 reviews

A traditional sauna is showcased in a rounded wooden structure, nestled among trees. The exterior features natural wood tones and a dark roof, inviting relaxation and wellness. The area presents an inviting ambiance, perfect for unwinding throughout the year.

Home in Yarmouth Port

Beachfront· Sauna· Screened Patio· 2Kings· DogsYes

4.91 out of 5 average rating, 33 reviews

A wooden deck is shown in a private backyard, featuring a dining table surrounded by blue chairs. Potted flowers add color, while tall trees provide shade, creating a serene outdoor space suitable for gatherings.

Home in West Yarmouth

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

4.98 out of 5 average rating, 163 reviews

A game area features a colorful 'Roll and Score' arcade game highlighted by vibrant blue lighting. The background displays a large Boston Red Sox-themed mural, enhancing the playful atmosphere. Beside the arcade game, a shuffleboard table contributes to the entertainment options available.

Home in Harwich

* Game Room, Linens, Quiet St, Central AC/Heat

Cottage rentals with a kayak

4.87 out of 5 average rating, 112 reviews

Large floor-to-ceiling windows frame a view of the lake, inviting natural light into the space. The open-concept living area features a comfortable seating arrangement, a dining table, and decorative elements such as floral centerpieces. Wooden beams highlight the high ceilings, enhancing the spacious feel.

Cottage in Falmouth

Spectacular Beach- front home, includes linen

4.94 out of 5 average rating, 124 reviews

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

4.98 out of 5 average rating, 204 reviews

A serene view of a crystal clear pond is framed by lush trees. The calm water reflects the blue sky and scattered clouds, creating a tranquil atmosphere. A wooden pathway leads to the water's edge, inviting exploration and relaxation.

Cottage in Dennis

★Waterview ★Pet Friendly ★Kayaks ★Trails ★

5 out of 5 average rating, 53 reviews

A well-maintained pathway leads to a serene cottage entrance, flanked by lush greenery and landscaped beds. A stone water feature creates a calming ambiance, while lounge chairs are positioned nearby for relaxation. Sunlight filters through the trees, enhancing the tranquil outdoor setting.

Cottage in North Eastham

Cape Cottage Escape

4.89 out of 5 average rating, 18 reviews

The tranquil scene captures a calm body of water reflecting a vibrant sky filled with scattered clouds at sunset. Shades of blue, orange, and yellow are visible, creating a serene atmosphere. The horizon gently blends with the water, inviting a peaceful moment of reflection.

Cottage in Wellfleet

1940s Classic Cape Cod Beach Cottage

5 out of 5 average rating, 13 reviews

The kitchen and dining area feature natural wood accents and large windows that provide views of the surrounding greenery. A wooden dining table with woven chairs is positioned near the window, and modern appliances are neatly integrated into the cabinetry, contributing to a bright and airy feel.

Cottage in Plymouth

Cozy, modern cottage on the shore of Long Pond

4.98 out of 5 average rating, 96 reviews

Row of charming cottages lined along a sandy beach, with white lounge chairs positioned for relaxation. The tranquil bay is visible in the foreground, while the skyline is seen in the distance, under a bright blue sky dotted with soft clouds.

Cottage in North Truro

Beachfront at Days' Cottages! Renovated, Kayaks!

4.94 out of 5 average rating, 17 reviews

The cottage exterior is showcased, featuring a charming purple façade with black shutters. A landscaped yard with a gravel pathway leads to a private deck area. Surrounding greenery includes trees and shrubs, creating a tranquil outdoor setting.

Cottage in Brewster

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

Other holiday rentals with a kayak

4.77 out of 5 average rating, 61 reviews

The house exterior showcases a two-story structure nestled among tall pine trees. The wood siding is complemented by large windows, allowing natural light to enter. A driveway leads to the house, with greenery and grass providing a natural and serene setting.

Home in Wellfleet

Wellfleet, MA. Cape Cod sleeps 8

Apartment in Provincetown

A coastal view is showcased from the private deck, with a glimpse of the harbor and outdoor seating. The kitchen area, visible through the open door, features a spacious counter and seating for four. Large windows enhance natural light throughout the space.

4.86 out of 5 average rating, 22 reviews

Beachfront Condo, Superb Location!

5 out of 5 average rating, 72 reviews

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 South Yarmouth

Sunburst Cottage on Long Pond

5 out of 5 average rating, 30 reviews

A cozy living area is visible, featuring brick walls and wooden beams overhead. A pink sofa and striped armchair are situated facing each other. Framed artwork and mirrors adorn the walls, with floral curtains allowing natural light to enter. The entrance to a bathroom can be seen in the background.

Flat in Provincetown

Waterfront-Private Deck-Kitchen- on Commercial Apt

5 out of 5 average rating, 55 reviews

The exterior of the apartment is shown, featuring a two-story building with textured wooden siding. The backyard presents a grassy area with seating options, including patio furniture. Access to balconies is visible, along with pink umbrellas and several windows that allow natural light into the units.

Flat in Centerville

Modern Luxury, Central Location, Bikes & Kayak

5 out of 5 average rating, 11 reviews

Home in Brewster

NEW! Water Views + Dog Friendly Cape Cod Retreat

5 out of 5 average rating, 87 reviews

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