
Holiday rentals with a kayak in Pittsylvania County
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Top-rated rentals with kayak in Pittsylvania County
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

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

Serenity &Sunsets- Family home SML on the water
Welcome to Smith Mountain Lake! Join us for your family vacation! Our home has 4 bedrooms, 6 beds, 3.5baths, baby & kid items, a fully stocked kitchen and more! The master & 2nd bedrooms have king beds. The 3rd has two full-size beds. The spacious basement bedroom has two beds, one king and one queen. There are 2 dining tables & spacious living room for family/friend gatherings. The home is lake front with a private dock, in a quiet neighborhood, families welcome, desk & wifi for remote working.

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

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.

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

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.

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

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!

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.

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.

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!

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
Popular amenities for kayak rentals in Pittsylvania County
House rentals with a kayak

We have water! Spacious with Gentle Slope and Dock

4 bedroom, 2 bath; Penhook Hideaway at SML

Stunning Lake Home w/ Private Dock, Spa, Fire Pit

Deep Water Dock + Hot Tub | Lakefront, Sleeps 12

Lake Haven - Hot Tub! Mountain Views!

Dock, Hot Tub, Outdoor Sauna, Fire Pit, Game Room!

Smith Mountain Lake quiet cove w/ kayaks & firepit

Lolli & Pop’s Lake Front Oasis
Cottage rentals with a kayak

Kayaks, Billiards Room, Outdoor Fireplace, Privacy

A Nautical Nook on Smith Mountain Lake

11-Acre Lakefront Escape w/ Two Cottages

The Cottage on Locust Lane, Waterfront On SML
Other holiday rentals with a kayak

On the Rocks SML

The StarBird: Waterfront with BIG views!

Little House at Leesville Lake

SML Retreat | Pool Table & Kayaks + Lake Amenities

SML Lake Retreat House

Waterfront house Private Dock!

Junie's Place (Lakefront Cottage)

Lakefront Retreat, Waterfront, Golf & Pools
Destinations to explore
- Pet-friendly rentals Pittsylvania County
- Rentals with pools Pittsylvania County
- Rentals with beach access Pittsylvania County
- Rentals with lake access Pittsylvania County
- House rentals Pittsylvania County
- Beachfront rentals Pittsylvania County
- Flat rentals Pittsylvania County
- Waterfront rentals Pittsylvania County
- Rentals with a hot tub Pittsylvania County
- Apartment rentals Pittsylvania County
- Family-friendly rentals Pittsylvania County
- Rentals with a kayak Virginia
- Rentals with a kayak United States
- Smith Mountain Lake State Park
- Hanging Rock State Park
- Greensboro Science Center
- Virginia International Raceway
- Fairy Stone State Park
- Guilford Courthouse National Military Park
- Liberty Mountain Snowflex Centre
- International Civil Rights Center & Museum
- National D-Day Memorial
- Martinsville Speedway
- Mill Mountain Zoo
- Percival's Island Natural Area
- Explore Park
- Taubman Museum of Art
- Mill Mountain Star
- Elon University
- Tanger Family Bicentennial Garden
- Virginia Museum of Transportation
- Harvester Performance Center
- SeaQuest Lynchburg
- Greensboro Country Club
- Amazement Square





