
Holiday rentals with a kayak in Pittsylvania County
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Top-rated rentals with kayak in Pittsylvania County
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$98 LAKEfront w/Dock HotTub Kayaks Canoe Sun. Free
Fun 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, Fireplace & Firepit w/Wood, Canoe & 4 Kayaks/LifeVests, Bikes w/Helmets, Screened Porch. Deck. Gas Grill. Activities for kids. Near Marina. Near State Park w/Hiking. Family/Pet Friendly. Lots of Parking. Sept-Dec. Sun.night free if book 2 nights w/check out on Sunday. $98 Mon.nights
4.89 out of 5 average rating, 160 reviews
Stunning Lake Home w/ Private Dock, Spa, Fire Pit
BookSmart Properties presents: Island Retreat! This gorgeous lakefront home offers a private dock, spa, firepit, and water views throughout the house! Sleeping up to 6 guests (1K, 1Q, 4Twins), Island Retreat is beautifully updated and equipped with everything you need for a perfect getaway to the lake. Two living areas w/ fireplaces & TVs, a modern kitchen, and plenty of outdoor space for dining or relaxing round out this lovely home. Bonus entertainment includes a PS5, cornhole, and horseshoes.
4.88 out of 5 average rating, 43 reviews
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
4.91 out of 5 average rating, 138 reviews
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
4.93 out of 5 average rating, 114 reviews
We have water! Spacious with Gentle Slope and Dock
Welcome to Heron Landing at Smith Mountain Lake! Your 3BR/3.5BA Lakefront retreat sits on SML’s North Shore, in a quiet and peaceful cove. Enjoy waking up to your beautiful, family friendly home featuring a private dock, kayaks, paddle boards and panoramic lake views. Enjoy the ease of cooking in your newly renovated kitchen with ample seating, granite counters, and stylish cabinets. Comfortable home equipped with 3 full baths, 3 beds + 2 additional sleeper beds, and 2 King master suites.
5.0 out of 5 average rating, 14 reviews
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.
5.0 out of 5 average rating, 35 reviews
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
4.99 out of 5 average rating, 400 reviews
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!
4.95 out of 5 average rating, 211 reviews
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.
5.0 out of 5 average rating, 30 reviews
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.
4.97 out of 5 average rating, 36 reviews
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!
4.96 out of 5 average rating, 186 reviews
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
4.76 out of 5 average rating, 123 reviewsPopular amenities for kayak rentals in Pittsylvania County
House rentals with a kayak

Sunset Paradise: A Private Retreat.
5.0 out of 5 average rating, 36 reviews
Smith Mountain Lake - Cedar Key Retreat
5.0 out of 5 average rating, 50 reviews
Deep Water Dock + Hot Tub | Lakefront, Sleeps 12
4.93 out of 5 average rating, 89 reviews
Lakefront Retreat w/ Fire Pit, Dock & Mtn Views
4.98 out of 5 average rating, 51 reviews
Lakefront 5BR | Dock, Beach, Hot Tub | Pets ok
5.0 out of 5 average rating, 14 reviews
Waterfront: Ideal Dock for Boats, Swimming +Arcade
4.94 out of 5 average rating, 34 reviews
Lolli & Pop’s Lake Front Oasis
4.9 out of 5 average rating, 20 reviews
Lake Haven - Hot Tub! Mountain Views!
4.96 out of 5 average rating, 55 reviewsCottage rentals with a kayak

Kayaks, Billiards Room, Outdoor Fireplace, Privacy
5.0 out of 5 average rating, 29 reviews
A Nautical Nook on Smith Mountain Lake
4.84 out of 5 average rating, 147 reviews
The Cottage on Locust Lane, Waterfront On SML
5.0 out of 5 average rating, 35 reviews
11-Acre Lakefront Escape w/ Two Cottages
5.0 out of 5 average rating, 30 reviewsOther holiday rentals with a kayak

The StarBird: Waterfront with BIG views!
4.96 out of 5 average rating, 57 reviews
Blue Heron - Peaceful Cove, Beach, Ping Pong
4.93 out of 5 average rating, 14 reviews
Little House at Leesville Lake
4.94 out of 5 average rating, 51 reviews
Dock, Hot Tub, Outdoor Sauna, Fire Pit, Game Room!
5.0 out of 5 average rating, 44 reviews
SML Retreat | Pool Table & Kayaks + Lake Amenities
4.98 out of 5 average rating, 51 reviews
SML Lake Retreat House
4.9 out of 5 average rating, 21 reviews
Junie's Place (Lakefront Cottage)
5.0 out of 5 average rating, 25 reviews
4br Lakefront Kayaks Game Room
5.0 out of 5 average rating, 27 reviewsDestinations 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
- Explore Park
- Percival's Island Natural Area
- Mill Mountain Star
- Taubman Museum of Art
- Elon University
- Tanger Family Bicentennial Garden
- Virginia Museum of Transportation
- Harvester Performance Center
- SeaQuest Lynchburg
- Greensboro Country Club
- Amazement Square





