Five of the Coolest Vacation Rentals for a Virginia Fall Getaway

By Sharon Smith

November 18, 2022

You don’t have to stay at just any old rental. Virginia has everything you could possibly want when it comes to creative rental properties. 

It’s always a good time to visit Virginia but fall might be the best time. It’s not too hot, not too cold. The stars are bright. The leaves have turned colors making the already spectacular mountain views a little extra special. Sitting outside roasting marshmallows under the stars at fire pit at one of Virginia’s many rentals sharing stories and laughs it doesn’t get much better than that. If you are looking for something more than your basic beach house or mountain cabin, Virginia has you covered. 

Our state has hobbit houses, tree houses, yurts, tipis, shipping containers, farmhouses, tiny houses, train cars, and so much more. We even found a pirate ship. If you can imagine it, someone has probably listed it as a Virginia vacation rental. Here are five rentals that just may be the coolest the Old Dominion State has to offer.

The Jolly Lodger Pirate Ship 


Have you ever wanted to be Capt. Jack Sparrow and command your own pirate ship, complete with a skeletal crew? Now is your chance. You can stay in this two-bedroom, 1.5-bath pirate ship in Callao, about 60 miles East of Richmond. This pirate ship sleeps four, has a kitchen, and a grill. The ship even offers a kayak in case some of your shipmates are rowdy. You can paddle away on the Yeocomico River for some me time. The 1.1-mile Yeocomico River is actually a tidal tributary and part of the Potomac River in Northern Neck. If you want to live out your Pirates of the Caribbean fantasies this is the place to do it. Book early. This rental also has been called the best tiny house on water. It also has been featured on the BBC, The Washingtonian and CBS. 

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Five of the Coolest Vacation Rentals for a Virginia Fall Getaway
Credit Blue Tipi and Hollandhouze

Blue Tipi 


It’s been deemed the Blue Tipi with a view. This is glamping at its finest. This gem is nestled off Interstates 81 and 64 near Lexington on a 200-acre family farm. The heated tipi offers views of the Blueridge Mountains, proximity to skiing, hiking, and even a drive-in movie theater, which is pretty cool. Still, the blue tipi is secluded enough to heal your stress and regain your balance. The hosts also invite guests to tour their garden, which is always good for the mind, body and spirit.  The tipi has one bed and can accommodate three guests. It has also been featured in The Pennyhoarder because at $97 per night is an absolute steal. 

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Five of the Coolest Vacation Rentals for a Virginia Fall Getaway
Credit James Station

James Station: Caboose With Industrial River Views


Pack your bike, your s’mores ingredients and may be a bottle of wine or two. Your perfect getaway is literally written on the side of this vintage caboose that overlooks the James River. Like the caboose says, you will love it. The James River Caboose includes a large fire pit, a pollinator garden and is near downtown Lynchburg, with its cute shops and restaurants. It also offers easy access to the Blackwater Creek Trail system, which is down the street. It is perfect for hiking or biking. This railcar can accommodate up to three guests. It offers one bedroom and two beds and a bath. There are plenty of windows and natural lighting to take in the gorgeous views. 

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Five of the Coolest Vacation Rentals for a Virginia Fall Getaway
The Shenandoah Yurt is a unique luxury retreat secluded in the mountains of the Shenandoah one mile from Shenandoah National Park The luxury yurt includes modern amenities such as a hot tub wood burning stove a large back deck pool table and board games CreditVirginia Tourism Corp <a href=httpswwwinstagramcomshenandoahyurthl=en>Oleksandr Mokrohuz IG account shenandoahyurt<a>

The Shenandoah Yurt


You won’t be roughing it in this yurt. The Shenandoah Yurt offers anything you could want for a fall getaway. Located one mile from Shenandoah National Park, this luxurious retreat has a hot tub, wood-burning stove, fire pit, a pool table, archery, and plenty of boardgames.It also has a large deck to lounge on at night and stargaze. The dark skies over Shenandoah make it a great for stargazing.  You can snuggle up under a blanket with a mug of hot chocolate and search for the big dipper. In late spring and early fall if the weather cooperates you might even be able to see the Milky Way.If you are lucky enough to have an electric vehicle, there is even a charging station, which makes it eco-friendly, too. 

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Five of the Coolest Vacation Rentals for a Virginia Fall Getaway
Welcome to a Different World Spectacular views mountain top chalets elegant dining conference facilities and a wide array of recreational activities await you at Primland Resort located on a beautiful estate in the heart of the Blue Ridge Mountains of Virginia Virginia Tourism Corporation

Primland Treehouse

2000 Busted Rock Road, Meadows of Dan

This is where luxury and childhood fantasies meet. Primland, Auberge Resorts offers three treehouses that sit high above the Dan River Gorge, offering stunning views of Kibler Valley. It honestly does not get more romantic than this. Guests have their own private wooden decks where they can enjoy a cup of coffee in the morning or a glass of wine at night while they look out over the valley. Or they can enjoy the stunning views from their king-size bed. The treehouses named Barn Owl, Cooper’s Hawk and Golden Eagle all have large windows that let in tons of natural light and offer spectacular views no matter where you are inside the treehouse. 

Meadows of Dan is just under a four hour’s drive from Richmond, but well worth the road trip. 

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