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Holiday rentals with a kayak near Assateague Island National Seashore

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Top-rated kayak rentals near Assateague Island National Seashore

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Guest favourite
Home in Chincoteague

Dragonfli Bay House on Chincoteague Island

Relax in this calm, stylish space. This home has been lovingly refreshed by its current owners. Every detail has been considered. Inside you will find well appointed rooms designed for function and comfort. Outside, tranquility awaits you. Enjoy morning coffee overlooking the water, kayaking on the bay, end the day relaxing by the fire. Head to Assateague to swim, surf fish or hike to the famed lighthouse. Return with the day's catch to utilize the fish cleaning station and outdoor shower.

4.94 out of 5 average rating, 160 reviews
Guest favourite
Home in Chincoteague

Island House: Kayaks, Bikes, Beach Gear & Firepit

Welcome to Happy Ours! Relax with the whole family at this peaceful Chincoteague home. Walk to the park (Pony Swim!). This beachy cottage offers all the charm with plenty of space, in a quiet area with a huge property. This is a family home that we enjoy with friends & family year-round. We would love to share that experience with you! If we can do anything to make your stay more enjoyable, don’t hesitate to reach out, and please kick back and relax and enjoy all that Chincoteague has to offer!

4.96 out of 5 average rating, 110 reviews
Top Guest favourite
Colorful armchairs with a fish pattern provide comfortable seating by large windows that offer views of the water and surrounding nature. A small green side table stands between the chairs, adorned with a vase of flowers.
Home in Ocean City

The Oliver House

This property boasts breathtaking views of the Ocean City skyline and is nestled in a quiet neighborhood in West Ocean City. Bring your boat, paddle boards, kayaks and firewood for the most incredible vacation. Crabs and clams are plentiful and the kids can enjoy playing in the small beach area while splashing or swimming in the bay. Although you may never want to leave, it's a short drive to Ocean City's beaches and boardwalk, Assateague Island and the quaint must-see town of Berlin, Maryland.

4.86 out of 5 average rating, 63 reviews
Top Guest favourite
Adirondack chairs are arranged in a semicircle facing a stunning sunset over Chincoteague Bay. The sky reflects hues of orange and pink, while the calm waters mirror the colors above. A firepit is positioned nearby, surrounded by tall grasses.
Cottage in Chincoteague

Waterfront-CI Bay sunsets-Amazing views

Wide expansive waterfront view of Chincoteague bay-awesome sunsets! 5 waterview rooms. The narrow bit of land across 3446 Main St. belongs to our property w/chairs + a firepit + water access to launch kayaks (2) provided! An open plan-coastal rustic design. Front sitting room w/sofa + high-top table. A large upscale kitchen, two sofas in living room, 2 bdrms, & sleeping loft + a tiny office with a twin murphy bed. Large deck-table, sofa + grill. Family home, not ideal for more than 3 adults.

4.96 out of 5 average rating, 170 reviews
Superhost
A bright living room showcases a spacious sectional sofa with warm, earthy tones. Two armchairs complement the seating area. A medium-sized television, featuring a beach scene, is positioned on a wooden entertainment unit, with a rug adding texture to the light-hued flooring.
Home in Ocean City

The Bayside • Entire House+Yard+Kayaks •Walk2Beach

🏖️ Quick walk to the beach 🌊 🏠 Spacious entire house + full yard 🛋️ 2 Living Rooms, 3 Bedrooms, 2 Bath, 7 beds 🍽️ Full Kitchen + charcoal grill 📍 Centrally-located, walking distance to top rated Bayside Skillet & Ropewalk Restaurant, bay and more 👯Plenty of space for everyone to spread out ☀️ Front porch table to enjoy coffee & sunsets🌅 🧺 High capacity washer/dryer in unfinished area of home 🛏️ New memory foam mattresses & provided linens. Book your memories today! 🛶 2 Kayaks

4.79 out of 5 average rating, 68 reviews
Top Guest favourite
Home in Ocean City

Hot Tub & Pool Table Waterfront Home | 4King Beds

Yes- Linens are included! (Bed sheets & bath towels) New pool table & jacuzzi!! Experience the ultimate Ocean City getaway this year, with unbelievable water views from every room & a private two-story wrap-around balcony. Enjoy 4 comfy king beds. The home is perfect for groups seeking relaxation & home away from home. Only 4.2 miles from the Ocean City Boardwalk! What else is included? Bonfire pit Parking area Shampoo-Conditioner-Body Wash Soaps Laundry Detergent Kayak Beach chairs

4.98 out of 5 average rating, 80 reviews
Guest favourite
Apartment in Newark

Relax at the Shorehouse

Our cozy, rustic, beachy apartment is close to all the area has to offer! We are nestled between Snow Hill and historic Berlin off Rt 113. We are about 15 min from West Ocean City and 12 miles from Assateague. Dining, shopping, and family activites are also nearby including a public boat ramp 5 min away to launch small watercraft and a playground with pavilion across the street. We recently renovated the apartment, and the decor was chosen to make guests feel at home at the Shorehouse!

4.88 out of 5 average rating, 129 reviews
Top Guest favourite
A two-story waterfront home is visible, elevated on stilts with a spacious deck featuring steps leading down to a private dock. Brightly colored kayaks are stored on the dock, and lush trees surround the property, providing a natural, serene backdrop.
Home in Chincoteague

Jay's Retreat: dock, kayaks, EV charger, bikes

Welcome to Jay’s Retreat, a charming waterfront oasis nestled in scenic Oyster Bay. This beachy 3-bedroom, 2-bathroom home accommodates up to 6 guests and is pet-friendly it an ideal space to vacation with your entire family. The spacious screened porch offers the perfect perch to savor your morning coffee with the sunrise or relax with friends and family while enjoying fresh, locally sourced seafood. End your days by the fire pit, soaking in the peaceful bay views and coastal breeze.

4.97 out of 5 average rating, 101 reviews
Guest favourite
A spacious houseboat is docked securely along the water's edge, featuring large windows and a deck area. The surroundings include trees and a sandy space, creating a coastal atmosphere. The sky displays soft clouds illuminated by the setting sun.
Houseboat in Snow Hill

"Jolly"- Houseboat Getaway

"Tiny house on the water"! Jolly is a 42ft Holiday Mansion. Baywater Landing buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & deck areas to enjoy! 35 mins from Ocean City & Assateague Island. 45 mins from Chincoteague Island. Jolly remains docked, but guests have access to kayaks and paddle boards at no additional charge. Baywater Landing is secluded- some even say "boring"- but we think that's the whole point!

4.88 out of 5 average rating, 186 reviews
Guest favourite
Home in Chincoteague

Bay View - Waterfront, Dock, Stunning Sunsets

Just a few miles to the Chincoteague National Wildlife Refuge & Assateague Island Beach, Bayview is the perfect place for your Chincoteague Island vacation! Located in the Prestigious Wildcat Community Enjoy Sunsets & Unobstructed Views of Chincoteague Bay from the two waterfront decks! New Deep Water Dock will be your favorite spot for fishing, crabbing or kayaking (2 kayaks provided). Relax by the water, fire pit or soak in the hot tub overlooking pristine marshes!

4.88 out of 5 average rating, 24 reviews
Top Guest favourite
A wooden dock extends over calm water, surrounded by tall trees. A pair of Adirondack chairs provide a peaceful spot to enjoy morning sunlight filtering through leaves, creating a serene atmosphere perfect for relaxation.
Home in Newark

Secluded Waterfront - Beach 15mi, Kayaks, Firepit

Casa Blue Heron is a 2,254 ft² (209 m²) custom waterfront home with a private dock, firepit, and water views throughout - nestled on a tidal inlet connected to Chincoteague Bay - and near Assateague, Berlin, Ocean City, Snow Hill, and much more. ★ "A private and tranquil setting where it is impossible not to relax and appreciate nature… Wish I had booked an extra day!" Add us to your wish list by clicking the ❤️ in the upper-right corner.

5.0 out of 5 average rating, 126 reviews
Top Guest favourite
A charming house with large windows is situated by the water, framed by lush greenery. A wooden dock leads from the house to the water's edge, surrounded by tall grass. Soft evening light highlights the structure, creating a serene ambiance.
Home in Ocean Pines

Charming Waterfront Cottage w/2 King Suites + Dock

Newly renovated, sparkling, spacious house with room for seven and waterfront views is waiting for you. Perfect for a single or double family getaway, girls weekend, or quiet retreat. *Please note this is a No Smoking and No Pet Property. **We are located in a quiet, residential neighborhood with lovely neighbors in close proximity. Please consider this when booking. ***We do not supply sheets and towels. Rental License #2162

4.99 out of 5 average rating, 148 reviews

Popular amenities for kayak rentals near Assateague Island National Seashore

KitchenWi-FiPoolFree parking on premisesAir conditioning

Holiday House Rentals with a Kayak

Guest favourite
The exterior of a two-story home features a combination of gray siding and stone accents. Large windows allow natural light to fill the interior, and a welcoming front porch leads to the main entrance. A neatly manicured lawn sits in front of the property.
Home in Berlin

Spacious, luxury, 5BD. Perfect for Families!

4.93 out of 5 average rating, 27 reviews
Top Guest favourite
Home in Newark

Waterfront Coastal Cottage w/ Kayaking & Crabbing

5.0 out of 5 average rating, 16 reviews
Guest favourite
A welcoming living room features a light-colored sectional sofa and two accent chairs. Natural light fills the space through several windows, illuminating a decorative rug. A wooden cabinet and wall decor complement the modern design, creating a comfortable area for relaxation.
Home in Berlin

Serene Family Getaway | OC & Assateague Adventures

4.92 out of 5 average rating, 26 reviews
Top Guest favourite
The living area features a spacious seating arrangement, including a dark sofa and cozy blue chair. Natural light is welcomed through large windows, while a wooden coffee table adds an organic touch. A Smart TV and decorative artwork enhance the inviting ambiance, leading to the dining area.
Home in Chincoteague

Chincoteague Island House "Sir Whelk-A-Lot"

4.86 out of 5 average rating, 74 reviews
Guest favourite
A bright living area features a large sectional sofa and a coffee table with decorative items. A flat-screen television is mounted on the wall, while a wall art piece depicting a beach scene adds color. Sliding glass doors invite natural light and overlook the porch.
Home in Berlin

Sunny Bayside Escape

4.9 out of 5 average rating, 20 reviews
Top Guest favourite
A welcoming approach to a spacious home is depicted, framed by tall trees reaching towards a bright blue sky. A neatly paved driveway guides the eye towards the house, with manicured lawns and colorful foliage adding to the inviting landscape.
Home in Ocean Pines

Coastal Oasis in Ocean Pines

4.97 out of 5 average rating, 79 reviews
Guest favourite
Home in Ocean City

Sands of Tide

5.0 out of 5 average rating, 16 reviews
Top Guest favourite
The front exterior of the house features a yellow facade with large windows and a welcoming doorway. A wooden deck is accessed by a set of stairs, and outdoor chairs are positioned for seating. Surrounding trees indicate a natural, wooded setting.
Home in Ocean Pines

Salty Serenity

4.96 out of 5 average rating, 48 reviews

Cottages with a kayak

Top Guest favourite
An aerial view highlights Rumbley Cottage's proximity to the shoreline and wetlands. The landscape features a mix of sandy beach, shallow waters, and expansive marshlands under a clear blue sky, offering a serene setting with natural beauty and tranquility.
Cottage in Westover

Rumbley Cottage on the Tangier Sound-Private Beach

4.99 out of 5 average rating, 266 reviews
Guest favourite
A Victorian cottage sits on a private island, surrounded by a serene lake. The green roof contrasts with the pastel exterior, while a footbridge leads to the shore. Lush grass and scattered trees create a peaceful landscape, with distant water views enhancing the setting.
Cottage in Hacksneck

Pretty Byrd Cottage, a Victorian Bayfront Getaway!

4.95 out of 5 average rating, 166 reviews
Guest favourite
A spacious deck offers breathtaking views of the water at sunset, with a stunning orange and pink sky. Four Adirondack chairs are arranged around a brown wicker coffee table, complemented by striped cushions. The serene water reflects the evening sky, creating a tranquil atmosphere.
Cottage in Onancock

A "True" Chesapeake Bay Waterfront Experience!

4.94 out of 5 average rating, 191 reviews
Top Guest favourite
A wooden boardwalk leads to a charming beach cottage, flanked by sandy beach and lush greenery. The cottage features large front steps, a light-colored exterior, and multiple windows offering views of the surroundings. The peaceful shoreline setting enhances the inviting entrance.
Cottage in Deal Island

Private Beachfront Cottage with 2 Bedrooms + Loft

4.94 out of 5 average rating, 100 reviews
Top Guest favourite
The exterior of the cottage is shown, featuring a welcoming entryway with stairs and a blue door. Two blue adirondack chairs are positioned on the well-maintained lawn, with a glimpse of the waterfront visible through large windows. Surrounding greenery enhances the outdoor setting.
Cottage in Smith Island

Levering Creek Cottage with private dock

4.97 out of 5 average rating, 274 reviews
Top Guest favourite
A spacious kitchen with a large central island is featured, complemented by white cabinetry and stainless steel appliances. Natural light fills the room through the window, illuminating the dining area with a wooden table and blue chairs nearby, creating an inviting space for gatherings.
Cottage in Lewes

Ebb & Flow Beach House - Lewes Bay Beach Retreat

4.99 out of 5 average rating, 224 reviews
Guest favourite
A serene sunset is captured over calm waters, with hues of orange and gold reflecting on the surface. Silhouettes of trees frame the scene, while a dock extends into the bay, creating a tranquil coastal atmosphere.
Cottage in Painter

Cottage by the bay location1/2 blockto the bay

4.9 out of 5 average rating, 127 reviews
Top Guest favourite
The exterior of a charming cottage is depicted, featuring a white wooden facade and a metal roof. A small stone patio with a bistro table and chairs sits at the entrance, surrounded by lush greenery and flowering plants. Two windows invite natural light into the space.
Cottage in Onancock

Little Cottage on the Creek

4.96 out of 5 average rating, 135 reviews

Cabin rentals with a kayak

Top Guest favourite
A rustic cabin is surrounded by tall pine trees, featuring a spacious deck with multiple seating areas. An American flag is displayed, while a grill is positioned nearby. Large windows allow natural light into the interior, creating a welcoming exterior view.
Cabin in Onancock

Awesome private off grid Creek front Cabin.

4.96 out of 5 average rating, 75 reviews
Top Guest favourite
Cabin in Tangier

Beach Road Oasis, Tangier Island, VA

4.98 out of 5 average rating, 52 reviews
Top Guest favourite
A bright living space is showcased with light blue walls and a wooden ceiling. A small dining area with two white chairs and a table is positioned near large sliding glass doors, providing a view of the waterfront deck and surrounding nature.
Cabin in Sussex County

The Boathouse on the Creek

4.97 out of 5 average rating, 39 reviews
Top Guest favourite
Cabin in Snow Hill

Luxury Historic Waterfront Cabin

5.0 out of 5 average rating, 18 reviews

Other holiday rentals with a kayak

Top Guest favourite
A spacious living area is highlighted by a large sectional couch adorned with decorative pillows. A coffee table with smooth stones is present, and a high-definition television is mounted on the wall. Floor-to-ceiling sliding doors open to a stunning waterfront view.
Townhouse in Ocean City

Ocean 14 - Amazing Waterfront Views & Beach Access

4.92 out of 5 average rating, 62 reviews
Guest favourite
A multi-level townhouse features a light-colored façade with multiple balconies and gabled roofs. Green shrubbery lines the front, complementing the welcoming aesthetic. Each unit has distinctly separated entrances, and the walkways are clearly defined, providing access to the main building.
Townhouse in Ocean City

Beach Paradise 110 - Beach Home at Broad Marsh OC

4.89 out of 5 average rating, 27 reviews
Guest favourite
Townhouse in Ocean City

Modern Canalfront Condo with Pool

4.94 out of 5 average rating, 17 reviews
Guest favourite
A bright and welcoming living area features comfortable seating, including a green sofa and patterned armchairs. A wall-mounted TV is positioned above a neutral console. Natural light streams through large windows dressed with light curtains, while coastal artwork adds decorative touches to the space.
Townhouse in Ocean City

New Waterfront House, Bay & Boardwalk!

4.96 out of 5 average rating, 67 reviews
Top Guest favourite
The exterior of a two-story townhome is depicted, featuring a symmetrical facade with dual peaked roofs. Large windows provide natural light, while well-maintained shrubs flank the entrance. A set of steps leads to the front door, which is framed by a covered porch.
Townhouse in Ocean City

The Salt Life at 94th St. Ocean City, MD

5.0 out of 5 average rating, 25 reviews
Top Guest favourite
A modern kitchen is visible, featuring a stainless steel refrigerator and a spacious countertop. Colorful bar stools surround a kitchen island. A cozy armchair with a decorative pillow complements the warm-toned walls and natural light from the windows, enhancing the open living area.
Condo in Ocean City

GREAT LOCATION! Remodeled 1BR condo w/ Bay View!

4.98 out of 5 average rating, 64 reviews
Superhost
A serene view of marshland and water under a pastel sky reflects soft pink and blue hues. The calm water is bordered by grass and stretches towards distant houses, creating a tranquil coastal landscape.
Townhouse in Ocean City

Bayfront, sunset view, 3 decks, dock + boat slip

4.81 out of 5 average rating, 31 reviews
Home in Chincoteague

Hopkin's House, Chincoteague Beach Vacations

4.71 out of 5 average rating, 224 reviews

Quick stats about holiday rentals with a kayak near Assateague Island National Seashore

  • Total holiday rentals

    Explore 20 holiday rentals in Assateague Island National Seashore

  • Nightly prices starting at

    Assateague Island National Seashore holiday rentals start at $192 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,140 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Assateague Island National Seashore holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Assateague Island National Seashore rentals

  • 4.9 Average rating

    Assateague Island National Seashore stays are highly rated by guests—averaging 4.9 out of 5!

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