
Holiday rentals with a kayak in Orange County
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Orange County
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

La Vita Bella at Lake Anna, Lake Front Resort Home
Live the Beautiful Life at La Vita Bella at Lake Anna. This gorgeous and spacious 6000+ SqFt home sits on a hill overlooking Lake Anna's most coveted cove. Take in morning sunrises with your coffee from one of two porches or make your way down to your private dock and watch the birds dive and fish jump. Enjoy time on the water exploring the cove in the two kayaks or take dip in the lake. This is a special place, and you and your guests will find new levels of relaxation while enjoying your stay.

The Lake Lodge: Private Slip, Lake Access, Hot Tub
Welcome to the Lake Lodge! You're invited to this peaceful retreat among a canopy of trees. The home is a 3 minute walk to the lake (public side), with a private slip, HOA sitting area, & boat ramp. When you aren't admiring the lake views from the HOA dock, savor the forested yard with built in firepit, cozy hot tub, & gigabit WIFI. After a long day of fishing, boating, or hiking, the home welcomes you with a stocked kitchen, outdoor grill, TVs in each room & a soaking tub. Relaxation awaits!

Lake Anna Lakefront Retreat
Rest, relax, repeat. Located at the most northern point of Lake Anna's public-side, this home offers renters an unforgettable experience to enjoy lakefront living, outdoor adventuring, nature at it's best with AT&T 5G and fiber connectivity. Home is 4,200 SQFT (2 levels), 4 BR, 4 Bath, 2 Kitchens, open / spacious floor plan with natural sunlight everywhere, private dock and firepits awaiting your enjoyment. For more information about the rental and local area please visit lkaretreat dot com

Lakefront at Turtle Cove
Enjoy the lake life in a peaceful quiet cove on the gorgeous large lake within Lake of the Woods. When not enjoying the newly renovated home with a vaulted ceiling great room, huge screened porch, and a desk and flat screen TV in each room, you can swim, float, kayak, or paddleboard in the quiet, secluded cove, or enjoy the 9 beaches or 2 community pools. Catch fish off the dock in one of the best fishing coves on the lake, and then warm up at night by the fire pit . Great for families.

Lakefront Access | Hour from DC | Kayaks Provided
Welcome to Virginia’s Lakeside Retreat, located in the tranquil Locust Grove neighborhood. This charming residence is perfect for vacation, featuring a spacious backyard with direct lake access. Enjoy the convenience of an on-site grill for delightful barbecues and dine al fresco in our comfortable outdoor seating area. This home is a haven for friends, families, or couples looking for a peaceful getaway. Book your stay and experience the perfect blend of relaxation and Virginia charm!

Home with beautiful mountain and river views
Welcome to the Madison House! This custom designed and built estate rests on a knoll overlooking 13.5 private acres on the Robinson River in rural Madison County, VA. Views of the Blue Ridge Mountains and direct Robinson River frontage makes this property a perfect destination for all four seasons. The outdoor space is ideal for friends and family gatherings and is ideally located near restaurants, wineries and breweries. The indoor space is both spacious and cozy for ample relaxing.

Waterfront retreat w/private dock/hot tub/kayaks
Homeport Harbor is the ultimate lake vacation home! Unwind in this spacious, cozy waterfront retreat located on the public side of Lake Anna! This 1,800 sq ft. home is located on one acre and is beautifully decorated; including completely all brand new furniture, kitchen upgrades and new mattresses throughout. Spend your days relaxing at the water’s edge on the private dock, screened in porch or large deck and your evenings roasting marshmallows gathered around the built-in fire-pit.

Lakefront Eco Retreat | 5BR, Dock & Sunset Views
Come experience lakeside cabin vibes at our modern Lake Anna log cabin—perfect for families and friends seeking space, style, and serenity! With five private bedrooms, a Tesla charger, private dock, and lakefront views, it’s ideal for reconnecting. Enjoy sunrise coffee on the screened balcony, family dinners with a view, and evening wine at the water’s edge. Thoughtfully designed for peaceful, eco-conscious stays where every detail invites you to slow down and savor.

Panorama Shores
Take a break and unwind at this peaceful expansive oasis. This lake front retreat boasts more lake access than you can imagine. Your own dock, pool, tennis court and huge yard to create memories with your friends and family. All linens provided including a set of outdoor towels for your use. The kitchen has been newly expanded and completely upgraded with 3 ovens, 2 islands and 2 sinks. This property was formerly listed as Anna Breeze. Now managed privately.

Life on the Lake, enjoy the peace and kayaks
Located within 20 minutes of both Fredericksburg and Culpeper, Virginia, this 2000 square foot home offers lakefront living on the 24-acre Keaton’s Lake within the gated community of Lake of the Woods. Keaton’s lake is ideal for fishing, swimming, kayaking or just lounging on the hammock or by the firepit enjoying the peaceful setting and beautiful view. Guests can also enjoy the 500 acre Main Lake and its beaches and parks.

Lake Anna Getaway • HotTub, GameRoom & Lake Access
Looking for lake access without the crowds? This beautifully designed home offers access to a private community boat slip, paddleboards, and peaceful surroundings—perfect for families or small groups seeking a relaxing escape. Enjoy evenings by the firepit, game nights in the open-concept living room, or morning coffee on the deck surrounded by nature. Just minutes from dining, wineries, and local fun.

Lakeside Escape- quiet space, w/ beautiful views!
★☆ ABOUT THIS SPACE ☆★ Welcome to your perfect getaway in Lake of the Woods! Whether you're sipping your morning coffee or unwinding in the evening, the scenery is sure to captivate you. This home features a full wrap-around porch, perfect for relaxing and taking in the surrounding views. You'll love easy access to the nearby beaches for a day of sun and sand.
Popular amenities for kayak rentals in Orange County
House rentals with a kayak

Harrison Hideaway

*Fall Fun*|4BR Lakefront|Fireplace| Firepit|BBQ

Dog Friendly w/fence | Lake | Hot Tub| Dock Slip

Sunrise view - Open water front - Dog Friendly

Knot Loggin’ Inn - Rustic charm with modern comfor

Paradise Found: Lakefront Home in Locust Grove

Wellness Spa Retreat-Hot Tub+Cold Plunge+Sauna+Gym

Lakefront Cabin Boat slip Wifi Fishing Firepit
Cabin rentals with a kayak

Bearfoot Den: Waterfront kayaks firepit jet tub

Lakefront Eco Retreat | 5BR, Dock & Sunset Views

7BR Lakefront Boat Dock, Kayaks & Amazing Sunsets

Cozy Cabin on the Cove
Other holiday rentals with a kayak

Blue House and a Pool

Avalon II - Lake Anna waterfront

Farmers' Landing

NEW 7BR Lakefront Lake Anna, Dock, Beach, Deck

Cozy Farm getaway on Lake Anna

Turtle Cove Cottage

Renovated Cottage on the Main Lake (close to DMV)

4BR Lakefront Lake Anna|Kayaks|Firepit|Boat Slip
Destinations to explore
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- Rentals with a kayak United States
- Kings Dominion
- Luray Caverns
- Early Mountain Winery
- Robert Trent Jones Golf Club
- Ash Lawn-Highland
- Massanutten Ski Resort
- Prince Michel Winery
- Lake Anna State Park
- Lee's Hill Golfers' Club
- The Foundry Golf Club
- Kinloch Golf Club
- Chisholm Vineyards at Adventure Farm
- Leesylvania State Park
- Hermitage Country Club
- Spring Creek Golf Club
- Farmington Country Club
- Blenheim Vineyards
- Grand Prix Raceway
- Birdwood Golf Course
- Cardinal Point Winery
- Little Washington Winery
- Glass House Winery
- Meriwether Springs Vineyard and Brewery
- Burnley Vineyards




