Holiday rentals with a kayak in Orange County

4.99 out of 5 average rating, 162 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, 30 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.

4.72 out of 5 average rating, 286 reviews

Chalet in Mineral

Private Lake Anna Waterfront Chalet w/dock/beach!

Your cozy lakefront chalet is steps away from deep water and fun adventure. With sandy beach, fire pit, fabulous dock area, hammock, canoe, kayaks, and SUP, you will enjoy your lake vacation. Room to bring a boat and/or jet skis w/ community boat launch. High speed Internet, swingset, on a large private lot with woods between neighbors. Large deck overlooking lake with gas grill. The property has 250' of prime main lake frontage with fishing, dining, and sunbathing on dock. Pet friendly!

4.93 out of 5 average rating, 27 reviews

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

Welcome to Soma Stays, a thoughtfully designed Wellness Retreat just 1.5 blocks from Lake Anna access. Our cozy vacation home is more than just a place to stay; it's an immersive experience crafted to elevate your well-being. Wellness amenities include a sauna, cold plunge, and fitness area. Our spacious home includes a game room and “speakeasy” area, 7 beds to sleep up to 10 adults or 12 w/ kids. From the moment you arrive, prepare to be enveloped in a world of relaxation and revitalization.

5 out of 5 average rating, 76 reviews

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, 48 reviews

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.

4.85 out of 5 average rating, 34 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.

5 out of 5 average rating, 60 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.

4.94 out of 5 average rating, 155 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.

4.92 out of 5 average rating, 95 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.

4.96 out of 5 average rating, 51 reviews

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.

5 out of 5 average rating, 69 reviews

Lake access w/boat slip, games, fire pit & hottub

Escape to Anna’s Oasis near Lake Anna, Virginia! This spacious home sits on 2 acres and is perfect for families, gatherings, or a romantic getaway. With 4 bedrooms and 3 bathrooms, it comfortably accommodates up to 11 guests. Enjoy the expansive outdoor space, great for outdoor activities, while the interior is stocked with games and entertainment for all ages. Experience the best of lakeside living!

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Popular amenities for Orange County kayak rentals

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Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

4.92 out of 5 average rating, 26 reviews

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

NoelleRating, 5 stars1 week ago

We had a great time on our first visit to Lake Anna. We hope to be back soon!

4.92 out of 5 average rating, 12 reviews

Home in Louisa

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

NickRating, 5 stars4 months ago

We really enjoyed our weekend getaway. The house had ample space for our group of 8. The kitchen was well-appointed with all the necessities to cook a good meal. We really enjoyed relaxing in the hot tub and hanging out on the big couch in the living room. If it wasn't so cold we would have loved spending time on the large back deck or sitting down by the lake.

5 out of 5 average rating, 10 reviews

Sunrise view - Open water front - Dog Friendly

BillRating, 5 stars2 weeks ago

Peaceful and then some. The house is located on a quiet dead end street…perfect for walking your 4-legged friend. Once inside the covered breezeway, make your way through the door and you’re greeted by a well appointed kitchen with plenty of room to prepare meals. From there you enter the dining and living room areas with plenty of seating. Hidden on this level of the house is a master bedroom with en-suite bath. Take a trip up via the spiral staircase and you will find 3 more bedrooms and another full bath. Head back downstairs to the main level and you will be met with the showstopper…the outdoor area. There’s an expansive deck with a large table and chairs plus deep seating for an evening relaxing while looking over the lake. A short stroll away lies the pier and all the water toys. We enjoyed the paddle boat and the canoe very much.

5 out of 5 average rating, 15 reviews

Home in Unionville

Knot Loggin’ Inn - Rustic charm with modern comfor

DomenickRating, 5 stars1 month ago

This is a beautiful, well-appointed home on a stunning piece of lakefront property. Our only regret is that we only stayed for a weekend. The outdoor spaces are beautiful. We had to choose between the spacious dock, the peaceful beach with a fire pit, the ground level patio with comfy furniture and fireplace or the second level decks with ample seating for our meals. Indoors was more of the same. The gourmet kitchen had everything we needed to prepare our meals. The bedrooms and bathrooms were clean and comfortable. We want to return when we have more time to enjoy this beautiful property.

4.77 out of 5 average rating, 22 reviews

Private Dock | Lakefront | Kayaks | 2 Firepits

TracyRating, 5 stars2 weeks ago

Loved our family time here! House was spacious and had everything we needed from the pack n play and kayaks to an easy boat rental. Alisha was always super responsive and friendly and very easy to book with. We wish we could have stayed longer!

4.78 out of 5 average rating, 67 reviews

Paradise Found: Lakefront Home in Locust Grove

KhariseRating, 5 stars1 day ago

It was a lovely home, loved the open space 1st level, it was inviting and bright. The king sized beds in every room made sleeping very comfortable for couples and the mattress, sheets and towels were clean. The bunk beds were also nice to have in the upstairs bedrooms. The check in was flawless (from lockbox code to security check in) and your response time was very quick. I did want to mention the house needs a bit of TLC particularly the outdoor area, the grill however worked perfectly with plenty of propane gas! Inside the home, thank you for providing the necessities: toilet paper, trash bags, paper towels, dishwashing liquid, etc. it definitely made staying at the house easier. Plenty of kitchenware and cooking supplies. Again some TLC but nothing major. Lastly, a “nice to have” would be a bigger tv in the living space and maybe some smart tv’s in the bedrooms. All in all the house was great and definitely provided a nice place for us to stay during my dad’s birthday. Thank you.

4.87 out of 5 average rating, 15 reviews

Lake Anna Castaway Beach Retreat

LorenRating, 5 stars9 months ago

A beautiful setting and a well appointed house, perfect for group gatherings. The lake at this end is very peaceful, lots of herons and geese, and the surrounding water and marshes are gorgeous to kayak through. Kitchen has everything you’d need for any range of possible meals. Beds very comfortable, bathrooms spotless and include soap/shampoo dispensers, and we loved having a range of seating areas. The hot tub is a really nice one! A few things that may be useful for future guests to pack or know: the dock and deck have no furniture if you want to pack beach chairs (we did). The water on this side is comparatively shallow but fine to put a pontoon or canoe in. We did wish for screen doors on the many large back doors to enjoy the breeze, but used the screened in porch for that. Don’t forget beach towels! The upstairs living room doesn’t have a TV, though the downstairs one is huge (this was fine for us but others may want to be aware when they pick bedrooms).