Vacation rentals with a kayak in Orange County

4.81 out of 5 average rating, 27 reviews

LakeAnna Waterfront, Dock, Pickleball, Hot Tub,16+

Rest, relax, repeat. Located at the northernmost point of Lake Anna’s public side, this home offers renters a memorable lakefront experience—outdoor adventure, nature at its best, Universal EV Charger plus 5G and fiber connectivity. The 4,200-sqft home (2 levels) features 6 BR, 5 baths, 2 kitchens, an open floor plan with natural light, private dock, and firepits ready for your enjoyment. For past reviews, please visit the following link from previous owners: https://www.airbnb.com/h/r3retreat

Outdoor spacesLocationHeating

4.94 out of 5 average rating, 171 reviews

Two kayakers are seen on calm water, paddling against a vibrant sunset backdrop. The sky is filled with shades of orange and purple, reflecting softly on the lake’s surface. Dark silhouettes of trees line the horizon, creating a peaceful and serene atmosphere.

Home in Mineral

Lake Anna Waterfront w/ Hot Tub & Private Dock

Welcome to Homeport Harbor — your relaxing Lake Anna escape. This spacious waterfront retreat on the public side of Lake Anna is perfect for couples, families, and group getaways. Set on a private one-acre lot, the updated home features stylish furnishings, an open kitchen, and comfortable mattresses throughout. Spend your days kayaking, swimming, fishing, or relaxing from the private dock, then unwind in the hot tub, screened porch, or around the fire pit under the stars. Lake life awaits.

LocationOutdoor spacesGetting around

4.99 out of 5 average rating, 217 reviews

A spacious outdoor area features a built-in firepit surrounded by ten Adirondack chairs, set among trees. Inside, an open living space includes a dining area, cozy seating, and natural light. A hot tub is positioned on a patio overlooking the dock and lake.

Home in Mineral

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!

Outdoor spacesValueParking

An expansive view captures the property nestled among lush greenery along the lake's edge. The home, surrounded by trees, features a spacious lawn that gently slopes toward the water, while the shimmering surface of the lake reflects the surrounding foliage.

4.97 out of 5 average rating, 29 reviews

Lakefront Villa on Lake Orange VA

In this 13.4 acres of wood and surrounded by the lake including half an acre private pond for fishing and have a nature walk through the wooded area and the peninsula. Quarter of a mile from the property on the other side of the lake there is a fishing bait store and boat rental. Whether you're seeking a peaceful retreat or an active lakeside adventure, our villa offers the best of both worlds. Book your stay today and experience the beauty and tranquility of Lake Orange in style. I

ValueOutdoor spacesAmenities

5.0 out of 5 average rating, 89 reviews

Three red Adirondack chairs are positioned in a grassy area overlooking a landscaped yard, with trees and bushes providing a natural backdrop. The soft glow of dusk casts a serene ambiance across the scene.

Home in Madison

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.

Outdoor spacesLocationPets

4.96 out of 5 average rating, 128 reviews

A peaceful scene is presented featuring a hammock suspended between trees overlooking a calm lake. The boathouse is visible in the distance, along with a dock extending into the water. Soft evening light reflects off the lake's surface, enhancing the tranquil atmosphere.

Home in Unionville

R&R at LAKE ANNA Waterfront 6 BR/6 Bath Dogs yes

R&R at Lake Anna...6 Bedrooms / 6 Full Bathrooms (17 total beds) It's time for some R&R! R&R at Lake Anna welcomes you to a comfortable lakefront home boasting 470 feet of water frontage on the public side of Lake Anna at the northwestern part of the lake. Nestled in over 3 acres of mature forest, R&R offers a modern cabin vibe. You will enjoy panoramic and stunning sunrise and sunset views of Lake Anna on one side and the privacy of being at home among the trees on the other.

Outdoor spacesLocationGetting around

4.91 out of 5 average rating, 123 reviews

Cabin in Orange

Lakefront Cabin • Dock • Sunset Views

Gather your people and settle into this spacious Lake Anna waterfront cabin, thoughtfully designed for families, multi-generational groups, and friends traveling together. Enjoy open lake views, a screened-in porch, a private dock, kayaks, paddleboards, and a well-equipped kitchen perfect for cooking and gathering around a large dining table. With plenty of room to spread out and welcoming hosts who are always available, this is a relaxed, comfortable lake home made for connection.

LocationOutdoor spacesHospitality

4.79 out of 5 average rating, 109 reviews

A spacious living room features hardwood flooring and large windows offering views of the lake. Comfortable seating includes a light-colored sofa and wooden chairs. A television is positioned near a stone fireplace, enhancing the room's cozy feel.

Home in Locust Grove

Lakefront Access | Hour from DC | Kayaks Provided

Welcome to Lakeside Serenity, located in the Locust Grove gated community of Lake of the Woods. This charming residence, situated in a quiet cove, features a spacious backyard with direct lake access perfect for swimming, fishing, kayaking, or lounging lakeside. Enjoy the convenience of an on-site grill for delightful barbecues and dine al fresco in our outdoor seating area overlooking the lake. This home is a haven for anyone looking for a peaceful getaway!

ValueOutdoor spacesCleanliness

5.0 out of 5 average rating, 18 reviews

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, 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.

Outdoor spacesLocationCondition

Superhost

Home in Mineral

5.0 out of 5 average rating, 3 reviews

Lakefront Lake Anna, Dock, Hot Tub, Game Room

A modern lakefront cottage on a quiet Lake Anna cove with a hot tub, private dock, and a Lake Anna's Dart Club game room. Sleeps 12 across 5 bedrooms (4 baths) — two king suites, a queen lake-view room, a queen lower-level walkout room, and a dedicated bunk room for kids. The vaulted, skylit great room frames the cove; a covered deck sits above the hot tub; and a wooded path slopes gently down to the dock. Modern, private, well-appointed, and peaceful.

ComfortParksSleep quality

Superhost

5.0 out of 5 average rating, 5 reviews

Stone Bridge Farm - 4 BR Riverfront House

This beautifully renovated 4-bedroom historic home, built in 1882, sits on 8 private acres with peaceful river access—perfect for families, wedding guests, retreats, and extended stays. Enjoy the charm of a classic Virginia estate with the comfort and convenience of modern updates, all while surrounded by nature. Note: The separate ADA apartment is not included in this listing but may be available separately.

Outdoor spacesLocationAccuracy

A spacious game room is presented, featuring a billiard table, ping pong table, and foosball table, all situated on light-colored flooring. Well-lit by recessed ceiling lights, the room offers a contemporary feel with a dark accent wall adorned with textured paneling.