Wine Country vacation rentals

Uncork and unwind along some of the country’s best wine destinations.
The deck of a romantic vacation rental in Guerneville, California.
The vineyards and villas in Kenwood, CA.

Two chairs with a wine bottle and glasses near a pool at a vacation rental in Kailua-Kona, HI.

Find your wine trip’s perfect pairing

Whether a romantic getaway or a weekend away with friends, take a trip out in search of award-winning wine, world-class cuisine, and postcard-perfect landscapes across the U.S.’s popular wine destinations. Reconnect with loved ones, explore the outdoors, and appreciate the (fermented) fruits of local artistry with a wine country vacation rental. Stay close to tours and tastings, then come back to your vacation home to recharge, refresh, or keep the good times rolling. Find homes with plenty of space for large groups, as well as amenities like hot tubs, fireplaces, pools, and views.

The exterior of a vacation rental in Santa Barbara surrounded by exotic plants.


Santa Barbara Luxe Villa

Located in Santa Barbara, California

This Mediterranean-style manor makes the perfect backdrop for a vacation of sipping wine and enjoying the ocean. Walk to the beach, shops, and restaurants, then come back to unwind by the fireplace. With room for six, you can bring friends or family along and enjoy delicious meals al fresco beside lovely views of the Santa Ynez Mountains.

Drone shot of a vacation rental on the lake with a dock surrounded by boats in Penn Yan, NY.


Finger Lakes, New York

Located between Syracuse and Buffalo, the Finger Lakes region is home to over 130 wineries. Clink your glasses with close friends at a wine tasting, embark on a waterfall hike or two, and settle into a slower pace with culinary delights and lakefront leisure. Get the most out of your visit and plan your trip in time for the Finger Lakes Wine Festival in late July.

Finger Lakes vacation rentals

More East Coast wine destinations

View of Lake Champlain
Lake Champlain Islands, Vermont

The Lake Champlain Wine Trail winds you through the area’s three dozen wineries and vineyards, not to mention the fresh produce farm stands, markets, and restaurants you’ll enjoy in between.
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Drone shot of Long Island.
Long Island, New York

Located on Long Island, Sparkling Pointe Winery & Vineyard is the only winery on the North Fork to produce exclusively sparkling wines, including Pinot Noir, Pinot Meunier, and Chardonnay.

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White sail boat on sea during daytime
St. Augustine, Florida

Name a better pairing than incredible wine and the coast. San Sebastian Winery offers tours and tastings through its sweet and light wines, with a rooftop patio and a gift shop.

smith mountain lake in summer
Smith Mountain Lake, Virginia

Outdoor recreation and fine dining meet in southeast Virginia. After a day of hiking, boating, or swimming, watch the sunset from the local vineyards as you sample their famous Cabernet Sauvignon.

Drone shot of Bahama Bay Resort overlooking the lake.
Davenport, Florida

Grab a vacation home or resort rental close to True Blue Winery and find relaxation in every sip. This hidden gem offers a delectable experience across both food and wine, perfect for any romantic vacation or trip with friends.

A bench looking at a pond in Clermont, Florida.
Clermont, Florida

Lakeridge Winery & Vineyards is a stand-out experience for all wine lovers visiting Florida. Try out the state’s largest winery and sample a few of its award-winning Muscadine grape wines.

Drone shot of Kailua Kona.


Kailua, Hawaii

Hawaii’s guava and pineapple harvest lead the way for popular fruit wines that pair well to any beach vacation. Vitis vinifera is also widely grown on the islands, making Viognier, Chenin Blanc, Syrah, and Malbec varieties to try on a wine tasting. Pour a glass to enjoy by the water as you watch the waves come in.

Deck chairs with tables and a pool in the background at a vacation rental in Hunt, TX.


Texas Hill Country

With a revered wine country, natural swimming holes, and fields of bluebonnets, Texas Hill Country is a treat to all the senses. Dig into delicious cuisine, shop antique markets, and hop from one tasting room to the next.

Texas Hill Country cabins and vacation rentals


Lake Leelanau, Michigan

Northern Michigan’s Leelanau Peninsula Wine Trail includes over 20 award-winning wineries, with fine dining options and incredible views to boot. Find tasting rooms on the water’s edge, fit in a few lakefront activities, or adventure your way through nearby Sleeping Bear Dunes.

Lake Leelanau vacation rentals

Lake Chelan


Lake Chelan, Washington

Lake Chelan is surrounded by tens of thousands of acres of fruit orchards and vineyards, making it an ideal destination for a wine country vacation. By day, take a scenic drive and stop by farm stands for apples, cherries, grapes, apricots, pears, and peaches. By evening, treat yourself to a few evenings of wine tasting through exceptional ciders and wine at any of the region’s 40 wineries.

Lake Chelan vacation rentals

More Pacific Northwest wine destinations

View of rolling hills and a vineyard.
Willamette Valley, Oregon

Oregonians are rightfully proud of the state’s vineyards, which specialize in world-class pinot noir. Take to the countryside’s rolling green hills and lounge out in luxury.

A view of Seattle, WA with the Space Needle and sky scrapers and a large mountain in the distance.
Seattle, Washington

Washington is best known for its cabernet, and with dozens of urban wineries throughout the city, you can fill an itinerary with finding your favorite.

Columbia Gorge

If the stunning scenery wasn’t enough, the Columbia Gorge’s renowned Cabernet Sauvignon and Merlot should definitely earn it a visit on your wine country vacation.

Portland, Oregon

With a vacation home in the city, you can easily plan a walking tour through wineries, or pair its famous Pinot Noir with a few food trucks if you dare.

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Exterior living area of a vacation rental in Quincy, WA.


Sunset Splendor at Cave B Ridge

Quincy, Washington

Looking to stay as close to the tasting room as possible? With beautiful views of the vineyard and the Columbia River, this chic and cozy condo rental is just a short walk away from the award-winning Cave B Winery, as well as the Spa at Sagecliffs and the Gorge Amphitheater. Savor fine wines (and some well-deserved R&R) on a getaway to remember.

California wine destinations

Southern California vacation rentals perfect for a wine getaway

Our favorite wine country rentals with pools

Wine vacations FAQ

Napa Valley is considered the wine capital of the U.S., but the California Wine Country region stretches across the Napa Valley and along a small portion of the northern coast, about 50 miles north of San Francisco. Each town has something different to offer, including Sonoma, Glen Ellen, Sea Ranch, Santa Rosa, Bodega Bay, and more.

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