The Best Winter Getaways in Virginia (3 Hours or Less From DC!)

Let’s talk about one of my favorite travel topics — the best winter getaways in Virginia, each less than 3.5 hours from DC. Winter is my favorite time to travel because, while the temperatures may not be ideal, there are often deals to be found, the crowds are quieter, and you won’t fight over a 7 p.m. dinner reservation.

I’m splitting these winter getaways in Virginia into two categories. The first being places where the stay is the destination and the second are charming towns.

Winter Getaways in Virginia: Less Than 3.5 Hours From DC

Stays as Destinations

Rosehill Cottage on the Rappahannock: Obviously I have to put my cottage front and center here! It’s my favorite cozy place to be with a fire and the expansive view of the river. On mild nights, the fire pit is a delight. It’s the perfect antiquing and oysters getaway during the off-season.

The Farmhouse at Veritas: We got married here during the winter so, of course, it’s near the top of my list. The pastoral setting, the vineyard a short walk down the road, and the traditional yet comfortable common spaces make this the best place to hide away during the chilly season.

Blue Rock Inn: I’ve only been to Blue Rock during the summer, but I can imagine it’s lovely during the winter. Stay on property for a multi-course dinner or explore the mountains around you.

The Ashby Inn: Ashby Inn is one of the most charming historic places I’ve stayed recently. Book a suite in the Schoolhouse with a fireplace for a cozy stay where you won’t even want to leave your room.

The Clifton: I just returned from a weekend at The Clifton (check it out on my Instagram story highlights!), and it was such a nice place to spend a winter weekend. You can have dinner and breakfast on the property, stroll around the grounds, or get out and enjoy Charlottesville.

Williamsburg Inn: I love Colonial Williamsburg any time of year, but particularly during the winter. The Williamsburg Inn property is right in town, so you can alternate between enjoying the stunning spaces within the hotel itself or exploring town.

The Jefferson Hotel: One of the characteristics that makes a hotel a wonderful place to spend a winter weekend is great common spaces. The Jefferson Hotel in Richmond does this beautifully. Not to mention, their rooms are the perfect place to order room service and feel luxurious.

Cities and Areas to Visit

Charlottesville: Obviously Charlottesville is at the top of my list. Whether you want vineyards (with legitimately good Virginia wine!), antiquing, hiking, or enjoying a bustling mid-size town, there’s something you can find here.

Staunton: Staunton is my most recent Virginia trip, and this small town won me over. There’s history, amazing restaurants, incredible mountain reviews, and darling local shops. You can stay right in town for the full experience of a walkable small town (yes, small towns can be walkable with everything you need — the dream, right?!).

Fredericksburg: Fredericksburg sometimes gets a bad rap as a traffic-ridden town along 95, but we had a wonderful time when we stayed there. It’s been a few years, but I wrote a blog post here.

Sperryville and Washington: When I think of winter, I think of the Blue Ridge Mountains as the backdrop, and that’s what you’ll get in these two charming towns. There are (obviously) incredible restaurants, as well as tiny towns to stroll through and hiking galore.

Shenandoah County: Just over the mountains, Shenandoah County has great small towns like Woodstock. We went in fall, but I’d love to go back in the winter and hole up in an Airbnb with a fireplace.

Middleburg: Everyone knows Middleburg does the Christmas Parade like no other, but the Red Fox Inn is also the most delightful place to stay during the winter. The dark and historic Tavern is the perfect winter spot.

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Where I’ve Written About a Few of These Virginia Getaways

Writing about these hotels for publications is something I love perhaps even more than covering them on my own blog and Instagram. Here are a few places I’ve written about these Virginia getaways.

Staunton in StyleBlueprint

Blue Rock Inn in Virginia Living

The Jefferson in StyleBlueprint

Ashby Inn in District Fray

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