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Holiday rentals with a kayak in Pittsylvania County

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Top-rated Accommodation with a Kayak in Pittsylvania County

Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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Superhost
A serene lake view is captured, showcasing calm waters reflecting the sky. The distant tree line and rolling hills provide a natural backdrop, complementing the peaceful atmosphere. Soft clouds drift above, adding depth to the landscape.
Home in Huddleston

Sunday Free Lakefront Doc/Lift HotTub Kayaks Canoe

Lakefront House...4 Bedrooms 7 beds HotTub Big Yard Secluded w/1.68 Acres. Most Desirable/Cleanest Water Location on SML. Best fishing. Amazing Views. No steps entrance. Gentle lot w/paved walkway to lake. Dock w/Boat Lift, Firepit w/Wood, Canoe & 4 Kayaks/LifeVests, Bikes w/Helmets, Screened Porch. Deck. Gas Grill. Activities for kids. Near Marina w/Boat Rentals. Near State Park w/Hiking. Family/Pet Friendly. Lots of Parking. June Special Sun.night free if book 2 nights with check out on Sunday

LocationValueKitchen

4.89 out of 5 average rating, 158 reviews
Top Guest favourite
A cedar cabin is set against a backdrop of serene water and mountains, with vibrant pink blooms in the foreground. The tranquil scene is enhanced by lush greenery surrounding the cabin, providing a peaceful lakefront atmosphere.
Cabin in Huddleston

Cute and Comfy Cabin, Stunning Lakefront Views,

Every season offers something special be it summer on the water, fall foliage, cozy winters by the electric fireplace, and blooming springs.   Book your stay & experience why guests return year after year. Wake up to panoramic lake and mountain views in a peaceful, no-wake 60 acre cove, perfect for fishing, relaxing, reconnecting, and making memories. Inside, this cabin you’ll find a playful bear-themed décor that guests of all ages love—adding a fun, memorable touch to your stay.  See Notes

Outdoor spacesLocationFamily

4.91 out of 5 average rating, 137 reviews
Top Guest favourite
Home in Moneta

Lakefront 5BR | Dock, Beach, Hot Tub | Pets ok

5BR Lakefront | Wheelchair Accessible | Pet Friendly | Hot Tub & Dock Lakefront luxury awaits! One of the largest wheelchair-accessible and pet-friendly vacation homes on Smith Mountain Lake. 5 bedrooms, 10 beds, and a gentle path to a private dock with a covered boat slip. Enjoy stunning lake views, a relaxing hot tub, a lakeside fire pit, and plenty of room for family and group gatherings. Fast Wi-fi, streaming TVs in a serene, peaceful setting. Relax and make lasting memories at the lake.

Outdoor spacesLocationAccess

5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Gretna

Gorgeous Lakefront Cabin Resort: 5400sqft 6BR, 5ba

Welcome to the Lake Bear Lodge family! 5,500sqft private lakefront resort w a gorgeous view feat: * King bed suite * 6br, 5 bath * Massive Game Room! ~20+ Arcades!!! ~75in TV ~Ping Pong ~2-player B-ball ~Pool Table ~Shuffleboard ~Bar w 2nd Fridge * Massive main living room w 75in TV * Private Dock * Firepit (propane) * Loaded Kitchen w Coffee Station * Huge Deck * 2 Screened Porch Areas (1 in master) * 6+ kayaks, Canoe * 2 paddleboards for rent, Message! * Whirlpool bathtub * Gas grill

LocationOutdoor spacesWalkability

4.93 out of 5 average rating, 114 reviews
Top Guest favourite
The exterior of the cottage is set against a backdrop of lush greenery. A covered porch invites relaxation, with seating available on both the porch and around a stone fire pit. A pathway leads to the entrance, surrounded by trees for privacy.
Cottage in Penhook

The Cottage on Locust Lane, Waterfront On SML

Nestled in the serene woods overlooking the beautiful waters of Smith Mountain Lake, The Cottage on Locust Lane offers the perfect blend of tranquility and opportunities for fun on the lake. Our charming cottage is located in a peaceful cove at the foot of Smith Mountain in Penhook, Virginia. Smith Mountain Lake has earned the title "The Jewel of the Blue Ridge Mountains" and our cottage is the perfect location to relax, have fun, and experience all our beautiful lake has to offer.

Outdoor spacesValueBarbecue

5.0 out of 5 average rating, 34 reviews
Top Guest favourite
A breathtaking sunset casts vibrant shades of orange, pink, and purple across the lake's surface. Silhouetted docks extend into the water, framed by distant mountains and a softly illuminated sky, creating a serene lakeside scene.
Condo in Moneta

Lake Lover's Paradise

Come to the lake! This spacious one bedroom top floor end unit is uniquely located between Napoli by the Lake restaurant and large outdoor swimming pool. Fantastic views of the lake from the large deck! Sleeps 2 adults and 2 small children under three. The following amenities are provided during your stay (Subject to season and repair): 2 Outdoor Pools Exercise Room Boat & Jet Ski Rental 1 Indoor Pool Hot Tub Courtesy Boat Slips Beach & Boat Launch Area Tennis & Pickleball Courts

Outdoor spacesValueCleanliness

4.99 out of 5 average rating, 398 reviews
Top Guest favourite
A serene lake view is captured at sunset, with a wooden dock extending into calm waters. Surrounding trees showcase vibrant autumn foliage, and distant mountains create a peaceful backdrop under a softly lit sky.
Home in Huddleston

Lakefront Retreat w/ Fire Pit, Dock & Mtn Views

Nestled off of desirable Craddock Creek, Crescent Bay sits on a gently sloping lot with a dock in a wide, private cove—perfectly positioned for stunning views of Smith Mountain. Enjoy peace, privacy and beautiful scenery. Designed with families in mind, the home features a fully renovated kitchen, updated bathrooms, and stylish, comfortable living spaces. Unlike many area rentals, we provide all linens, towels, and essential supplies—saving you time, money, and packing stress.

ValueLocationCondition

4.98 out of 5 average rating, 49 reviews
Top Guest favourite
A lakehouse is framed against a vibrant sunrise, with soft hues of orange and pink reflecting on the tranquil water. The structure features a wraparound deck, and a slight mist hovers above the lake, enhancing the serene atmosphere of the secluded setting.
Home in Pittsville

Lakehouse on Leesville Lake in Bedford County VA

This secluded, 3 bedroom lakefront home was renovated In 2019. My late wife Gail and I installed a new kitchen, vinyl plank flooring, new well, and new decks (both wraparound and lower deck.) The home is located about an hours drive from Lynchburg, Roanoke or Danville. Enjoy our private dock and boat ramp for fishing, watercraft, swimming, and nature watching! Keep an eye out for wildlife, both great and small! Great Blue Herons, Eagles and Osprey are personal favorites!

LocationOutdoor spacesComfort

4.95 out of 5 average rating, 210 reviews
Top Guest favourite
The image showcases a serene landscape featuring a stone cottage set on a gently sloping green meadow. The view extends toward a tranquil lake, bordered by trees and spring foliage, under a clear blue sky.
Cottage in Penhook

11-Acre Lakefront Escape w/ Two Cottages

Two private cottages set 70 yards apart on 11 scenic acres with a rolling meadow and 200+ ft of waterfront with private dock. Enjoy fishing, canoeing, wiffleball, bucket golf, darts, grilling, and evenings by the firepit under incredible stars. Relax on the large patio with mountain and lake views. Rent a boat nearby and tie up at the dock. Minutes to restaurants and groceries- perfect for family getaways, golf trips, and exploring SML region. A truly one-of-a-kind escape.

LocationValueIndoor spaces

5.0 out of 5 average rating, 30 reviews
Top Guest favourite
Home in Huddleston

Cozy SML Lakeside Cottage with Dock & Kayaks

Escape to this cozy lakeside cottage—perfect for couples or small families. Enjoy stunning views, direct lake access, and peaceful vibes. Lounge on the private dock or deck, swim, fish, or paddle out with two included kayaks or an inflatable paddleboard. A gentle sloping lawn leads to the water, plus a boat ramp (9'8" wide) and a private dock make lake adventures easy. Whether sipping coffee at sunrise or exploring the lake, this retreat blends comfort with outdoor charm.

Outdoor spacesLocationQuiet

4.97 out of 5 average rating, 32 reviews
Superhost
Home in Huddleston

Diving Board, Waterslide, Private, Lakefront

Welcome to this peaceful & private 1-acre A-Frame lakefront escape on stunning Smith Mountain Lake, VA! Enjoy sweeping wide-water views, breathtaking sunsets, and mountain vistas from four serene outdoor living spaces. Jump in the crystal clear lake from the dock’s diving board, race down the waterslide, or just relax in total privacy. Peaceful, fun, and unforgettable, this is lake life at its best!

Outdoor spacesValueLong stay

4.96 out of 5 average rating, 184 reviews
Superhost
Condo in Moneta

Bernards Landing NEXT2Pool (OpenTill 10/15 Heated)

Best Location at Bernard’s Vacation Properties – BookBernards This beautiful, larger one-bedroom corner unit is ideally located in the Dockside section at Bernard’s Landing, offering beautiful lake views on one side and the uncrowded outdoor pool on the other. The heated outdoor pool is right next to the condo and open through October 15, making it perfect for extended lake-season stays. BOOK TODAY

LocationOutdoor spacesCleanliness

4.75 out of 5 average rating, 122 reviews

Popular amenities for Pittsylvania County kayak rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Holiday House Rentals with a Kayak

Top Guest favourite
The exterior of the home is framed by lush trees, with a view of the lake visible beyond. The sunset casts warm colors across the sky, creating a peaceful ambiance. A gravel driveway leads to the house, enhancing accessibility and inviting exploration.
Home in Moneta

Serenity &Sunsets- Family home SML on the water

LocationOutdoor spacesLayout

5.0 out of 5 average rating, 71 reviews
Top Guest favourite
A serene lakefront view showcases a wooden dock with a shaded area and a boat slip, surrounded by lush trees. The calm water reflects the greenery and distant hills, creating a peaceful atmosphere. A gentle pathway leads from the lawn to the dock.
Home in Huddleston

Smith Mountain Lake - Cedar Key Retreat

Outdoor spacesLocationIndoor spaces

5.0 out of 5 average rating, 48 reviews
Guest favourite
A fire pit surrounded by several light blue Adirondack chairs sits on a gravel area, with a view of the lake and a covered dock in the background. Lush greenery lines the shore, creating a serene lakeside setting.
Home in Penhook

4 bedroom, 2 bath; Penhook Hideaway at SML

ValueLocationTV

4.88 out of 5 average rating, 82 reviews
Guest favourite
Home in Penhook

Lolli & Pop’s Lake Front Oasis

LocationOutdoor spacesComfort

4.9 out of 5 average rating, 20 reviews
Guest favourite
An aerial view showcases the serene landscape of Smith Mountain Lake, surrounded by lush green trees. The gentle slopes lead down to the water, where a private dock is visible along the shoreline, complementing the tranquil setting and inviting outdoor activities.
Home in Huddleston

Smith Mountain Lake quiet cove w/ kayaks & firepit

Outdoor spacesLocationShared spaces

4.94 out of 5 average rating, 96 reviews
Guest favourite
A view of the lake retreat house nestled among trees, showcasing a wooden walkway leading to the entrance. The parking area is visible, with a vehicle parked nearby, while steps descend towards the house, framed by vibrant greenery.
Home in Huddleston

SML Lake Retreat House

Outdoor spacesLocationComfort

4.9 out of 5 average rating, 21 reviews
Guest favourite
Home in Pittsville

Zen at Marker 10* Lakefront with Hot Tub!

LocationOutdoor spacesKitchen

4.95 out of 5 average rating, 19 reviews
Guest favourite
Home in Penhook

Deep Water Dock + Hot Tub | Lakefront, Sleeps 12

Outdoor spacesLocationGetting around

4.93 out of 5 average rating, 88 reviews

Cottages with a kayak

Top Guest favourite
A serene lakeside view is presented from the balcony, framed by tall trees with autumn foliage. The shimmering water reflects sunlight, while a small dock and boathouse are visible along the shoreline, enhancing the tranquil atmosphere of the surroundings.
Cottage in Huddleston

Kayaks, Billiards Room, Outdoor Fireplace, Privacy

ValueOutdoor spacesBathroom

5.0 out of 5 average rating, 29 reviews
Guest favourite
A gently sloping yard leads to a private dock with a gazebo in the background. The dock features seating and planters, surrounded by serene water. Adironack chairs are positioned on the lawn, inviting relaxation amid the colorful autumn foliage.
Cottage in Huddleston

A Nautical Nook on Smith Mountain Lake

LocationOutdoor spacesWalkability

4.84 out of 5 average rating, 146 reviews
Top Guest favourite
The image showcases a serene landscape featuring a stone cottage set on a gently sloping green meadow. The view extends toward a tranquil lake, bordered by trees and spring foliage, under a clear blue sky.
Cottage in Penhook

11-Acre Lakefront Escape w/ Two Cottages

LocationOutdoor spacesPets

5.0 out of 5 average rating, 30 reviews
Top Guest favourite
The exterior of the cottage is set against a backdrop of lush greenery. A covered porch invites relaxation, with seating available on both the porch and around a stone fire pit. A pathway leads to the entrance, surrounded by trees for privacy.
Cottage in Penhook

The Cottage on Locust Lane, Waterfront On SML

ValueLocationGetting around

5.0 out of 5 average rating, 34 reviews

Other holiday rentals with a kayak

Guest favourite
Cabin in Pittsville

Little House at Leesville Lake

ValueOutdoor spacesComfort

4.94 out of 5 average rating, 48 reviews
Top Guest favourite
The exterior of the modern home is showcased, featuring large windows with views overlooking the calm waters. A spacious dock extends from the property, complemented by lush trees in the background and a clear blue sky above.
Holiday home in Huddleston

The StarBird: Waterfront with BIG views!

ValueLocationBathroom

4.96 out of 5 average rating, 56 reviews
Top Guest favourite
Home in Moneta

Junie's Place (Lakefront Cottage)

LocationOutdoor spacesKitchen

5.0 out of 5 average rating, 22 reviews
Guest favourite
A custom-built home is presented with a blend of modern and traditional architecture. The exterior features a white facade with dark wood accents, complemented by a spacious driveway leading to a two-car garage. Bright blue chairs are placed on the front porch, surrounded by lush green grass and trees.
Home in Moneta

Smith Mountain Lake Retreat

Outdoor spacesLocationAmenities

4.97 out of 5 average rating, 30 reviews
Superhost
Home in Huddleston

Smith Mountain Sunrise - Party Deck, Hot Tub

LocationAccessView

5.0 out of 5 average rating, 4 reviews
Top Guest favourite
The image captures a scenic view of a serene lake bordered by lush greenery and trees. Fluffy white clouds drift in a bright blue sky, while the calm water reflects the surrounding landscape. Houses are visible on the far shore, enhancing the peaceful ambiance.
Home in Huddleston

Smith Mountain Lake Retreat on Peaceful Cove - 4BR

LocationOutdoor spacesAmenities

4.93 out of 5 average rating, 56 reviews
Superhost
A gravel area is surrounded by lush greenery, featuring a circular arrangement of dark blue Adirondack chairs encircling a stone firepit. The tranquil lake is visible in the background, along with a private dock extending over the water, framed by trees and gentle hills.
Home in Huddleston

Blue Heron - Peaceful Cove, Beach, Ping Pong

LocationOutdoor spacesKitchen

4.93 out of 5 average rating, 14 reviews
Top Guest favourite
Home in Moneta

4br Lakefront Kayaks Game Room

Outdoor spacesLocationQuiet

5.0 out of 5 average rating, 26 reviews

Destinations to explore