Holiday Travel Guide 2026: 6 Getaways Worth Packing For

Sometimes the best gift under the tree is a boarding pass, or at least a set of car keys and a very good excuse to leave town.

Whether you're escaping with your partner, rounding up the girls or finally taking that solo trip, these six places trade holiday chaos for something you'll actually remember. Some are a long weekend away. Others are worth the passport. All of them come with insight from the people who know them best.

Sevierville, Tennessee: A tiny home above a secret cave

Best for: couples, dog moms and anyone who's slightly over hotels.

The Smokies are the kind of place you think you've already seen, until you find Sojourn Lodging (Instagram · TikTok). This 11-acre village of design-forward tiny homes sits in the mountain foothills near Pigeon Forge and Dollywood, with four styles that sleep three or four.

The real twist is underneath you. A three-story private cave system runs below the property, and guests can explore it on a guided Cave Adventure. Back above ground, claim a fire pit, walk the trail with your dog, and let the phone die. The owners are serious dog people, and they've given more than $10,000 to the local Sevier County Animal Hospital.

Dundee Hills, Oregon: Wake up in wine country

Best for: girls' trips and slow mornings.

Instead of driving to the tasting room, stay at it. The guest houses at Stoller Family Estate (Instagram) put you among the vines in the heart of the Dundee Hills. The Wine Country Cottage suits a couple or a few friends, and the Estate House sleeps up to eight, which makes it a very convincing group text.

Every house has a kitchen, so stock up and plan one long, slow dinner in. Then spend an afternoon in the tasting room, at the winery that became the world's first LEED Gold certified winery. The tasting room is open daily from 10:30 a.m. to 5:30 p.m. Reservations are encouraged, but walk-ins are always welcome.

Chicago: A distillery date with a backstory

Best for: a city weekend with substance.

Chicago in December deserves a stop on Malt Row, the city's craft-beverage district. KOVAL Distillery opened in 2008 as the first distillery in the city since the mid-1800s, and it's 100% woman owned. Founder Sonat Birnecker Hart left a tenured professorship to build it, then went to Springfield to help change the state's liquor law so craft distilleries could offer tours and tastings at all.

Book the Classic Tour, which ends with a guided tasting of three spirits, then settle into the tasting room at 4241 N. Ravenswood Ave. It's about 20 minutes from downtown, and tours can sell out on weekends, so reserve ahead.

Southern California: See another side of LA

Photo: Vitor Rodrigues

Best for: a sunny break with culture on the side.

Just outside Los Angeles, Visit Conejo Valley brings together Thousand Oaks and Agoura Hills, with 15 lodging properties plus outdoor recreation, arts and tasting experiences. Time your stay around The Nutcracker, with three showings Nov. 28 to 29 at the Bank of America Performing Arts Center, or World Ballet Company's version with a live orchestra in December. For more festive stops, try Holidays in the Village, the Ice Rink at The Oaks or the Holiday Ice Rink at The Lakes.

Then drive into Hollywood for dinner at Flavors from Afar. Founder Meymuna Hussein-Cattan has reopened it as a Pan African bistro and wine bar, with one of the only African wine collections in LA.

Southern Spain: Ten minutes from the crowds

Best for: a winter sun escape that doesn't feel like everyone else's.

Simon Granville of Nero Line, who runs villas and private drivers across Spain, says the recommendation he gives clients most now isn't a city, it's distance from one. He points them to towns like Vejer de la Frontera, about ten minutes inland from the coast. It still feels undiscovered, it costs less than anything beachfront, and a beach day is still easy. Inland Mallorca works the same way, a short drive from the ports but in a different price bracket.

Tuscany: Eat like you live there

Best for: the woman whose wish list is really just one perfect table.

Licensed culinary guide and certified olive oil sommelier Christy Palma of Tuscany Flavor (Instagram) has spent 10 years guiding visitors through Italian food and wine. "Winter holidays in Tuscany are all about slowing down, eating seasonally, and discovering local traditions," she says.

That means cucina povera classics like ribollita, a winter soup of cannellini beans, Tuscan black kale, vegetables and bread, and peposa, a rich beef stew slow-cooked with red wine, garlic and black pepper. The olive harvest runs from October into early December, so it's a beautiful time for a tasting or a visit to a traditional mill. Book a tour and taste what she calls "our local liquid gold."

Pack like you've done this before

The trip goes better when your bag isn't working against you. Fora-certified travel advisor Krystal Wilson of 3ozs is the woman to know for carry-on-only travel, and her shop's TrekTote 12-Piece Women's Premium Travel Hygiene Kit ($18) handles the toiletries in one bag. There's a 15-piece men's kit ($23) for your travel partner.

Add a FOUR: Organics lip balm three-pack ($24) for dry plane air, and tuck in Gigawatt's Coffee Sample Packs ($21.99) so hotel coffee never gets the last word. For the flight, pack a copy of Sarah Aviram's travel memoir The Scenic Route.

The REEL BIZ take

The tree will still be there when you get back. Pick the place that made you pause, send one text to the friend who always says yes, and book it.

For more escapes, explore RB Travel. Staying home this year? Our Guide to the Perfect Holiday Party and 2026 Holiday Gift Guide have you covered.

Frequently asked questions

Where should I go for a holiday getaway in the U.S.?
For something different, try a tiny home in Sevierville, Tennessee, a wine country guest house in Oregon's Dundee Hills, or a city weekend in Chicago.

What's a good girls' trip for the holidays?
Stoller Family Estate's guest houses in Oregon are a strong choice, since the Estate House sleeps up to eight and has a kitchen for group dinners.

Is Sojourn Lodging pet friendly?
Yes, Sojourn offers pet-friendly stays. Check the current pet policy and fees before you book.

How can I save money on a trip to Spain?
Stay near the coast instead of on it. Nero Line's Simon Granville recommends towns like Vejer de la Frontera, about ten minutes inland, which cost less than beachfront stays.

Want more cinematic escapes and insider tips? Explore RB Travel and join the Insiders Collective.