Holiday rentals with a kayak in Orange County

4.99 out of 5 average rating, 169 reviews

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, & high speed 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!

4.87 out of 5 average rating, 39 reviews

Blue House and a Pool

Relax at Lake Anna with friends and family at your own pool, hot tub and dock. Blue house boasts numerous spaces for entertaining and private chill time. House features 4 bedrooms, 3 large couches and 3 full bathrooms. The gourmet kitchen is fully stocked and ready for a home cooked meal after a full day on the lake. Tim's at Lake Anna is a short car ride or boat ride to enjoy a meal and cocktail. The Cove and Lake Anna Plaza at the 208 bridge are close by including boat and jet ski rentals.

Superhost

Home in Louisa

4.92 out of 5 average rating, 13 reviews

3 Acre 5BR Resort: private pool, hot tub boat dock

Gather your loved ones at a secluded 5BR lakehouse on 3 lush acres at Lake Anna. Dive into the new heated Salt-Water Infinity pool & hilltop lake view hot tub, soothe muscles in the sauna, or spark friendly rivalries in the game room and volleyball court. Cook up joy in the fully stocked kitchen and unwind by the fire under crystal clear starry skies. Serene water views, fireside chats, and room for every adventure, this is where cherished memories are made—your ultimate private escape awaits!

5 out of 5 average rating, 85 reviews

Home in Orange

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

5 out of 5 average rating, 53 reviews

Home in Locust Grove

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.

Superhost

Home in Locust Grove

4.83 out of 5 average rating, 42 reviews

Harrison Hideaway

Introducing Harrison Hideaway, a peaceful family friendly lake front getaway at Lake of the Woods! The full renovation of this lake front home is now complete & is available for rent to family groups. Our house features 5 bedrooms, 3 full baths, a sunroom, a great room with kitchen, dining/family room with lake views & a lower level rec room with ping pong table. You can also charge your electric car in the carport with our level 2 charger. We also have a canoe, kayak and paddle boards.

4.9 out of 5 average rating, 70 reviews

Secluded Lakefront | Private Pool | Dock | Hot Tub

**Discover Ultimate Luxury at LesLee at the Lake: a Deep Water Lakefront Haven with Private Inground Pool, Hot Tub, and Dock** Nestled on the public side of Lake Anna, this picturesque 2.63-acre secluded property offers stunning waterfront views, a boat house for easy water access, and a lakefront fire pit. Our expansive and luxurious 9,000 sq. ft. home with game room, spacious kitchen, and movie theater, is ideal for an unforgettable escape and perfect for accommodating large groups.

5 out of 5 average rating, 68 reviews

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.

5 out of 5 average rating, 19 reviews

Home in Orange

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

4.94 out of 5 average rating, 160 reviews

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.

4.9 out of 5 average rating, 100 reviews

Cabin in Orange

Lakefront Eco Retreat | 5BR, Dock & Sunset Views

Retreat to lakeside luxury 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.