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6 Romantic Winter Weekend Getaways for Couples

Winter ushers in a breath of fresh air alongside a cold, crisp breeze. Up North, snow blankets various landscapes across the United States, creating storybook-worthy wonderland scenes. Venture down south for warmer weather and quiet, outdoor attractions. There’s a romantic essence to this time of year. 

We’ve compiled a list of some noteworthy winter weekend getaways for couples. Read on to learn more.

Winter Getaway Destinations

“Winter is the time for comfort, for good food and warmth, for the touch of a friendly hand and for a talk beside the fire: it is time for home." — Edith Sitwell

Find your home away from home at a Select Registry property in any one of the following winter weekend getaway destinations. 

1. Cleveland, OH

Cleveland, OH, is the perfect destination for those seeking an enchanting snowscape. Layer up and head outdoors. Consider boarding the “Polar Express” for a train ride along the Cuyahoga Valley Scenic Railroad. Check out the Metroparks’ chalet in Strongsville for sledding down a 1,000-foot ice sheet. You might even enjoy ice skating at Wade Oval! 

Stay at J Palen House

J Palen House is a historic bed and breakfast situated in the heart of the Historic Ohio City District! While the locale is nationally recognized for its dedication to fresh food, micro-breweries, and craft cocktails, the property is also known for its charm, sophistication, and luxurious amenities. 

J Palen House

2. Sunderland, VT

It’s no secret that Vermont is an excellent destination for snowsports! Couples will find a variety of exciting outdoor adventures in Sunderland, VT. For example, you can indulge in everything from dog-sledding and sleigh rides to skiing and snowmobiling. End your night with a cozy winter dinner at a romantic establishment such as Silver Fork or SoLo Farm & Table.  

Stay at Hill Farm by Sagra

Stay, tucked away, on fifty picture-perfect acres at Hill Farm by Sagra. This boutique property offers a stunning collection of guest rooms and cottages that allow for an authentic, upscale Vermont experience. Take in the stunning valley views on a rambling porch and revel in the thoughtful details that abound throughout the property. 

Hill Farm by Sagra

3. Willamette Valley, OR

Winter may be one of the best times to visit this world renowned wine region in Oregon.  After the final grape clusters are plucked from the vine, the time known as cellar season begins.  Winemakers light fires in their tasting rooms, and host a range of special tasting events.  In addition to wine tasting there are other great options.  Check out Christmas in the Garden in December or the Truffle Festival in January and February.  Winter is a great time to plan a cozy romantic getaway.

Stay at Youngberg Hill  

Retreat from the rest of the world with your sweetheart on a 50-acre hilltop surrounded by exquisite vineyards and views. This inn has an amazing 30-year old vineyard that is farmed organically and is known for producing award winning wines, dedication to sustainability

Youngberg Hill

4. Louisville, KY

Louisville, KY, draws visitors year-round. From shopping and museum-hopping to dining and exploring the outdoors, couples will find a host of exciting activities to keep them entertained during their stay! You could easily make it a point to try multiple versions of Louisville’s notable dish, “hot brown,” at various restaurants across the city! 

Stay at Chateau Bourbon 

Find comfort in the upscale accommodations at Chateau Bourbon in Prospect, KY. Here, you will find a perfect balance luxury and down-home charm. The sweet, southern hospitality complements the high-end amenities, decor, and style. Additionally, there’s no better place in the region to sample some of the best local bourbons! 

Chateau Bourbon 

5. New Smyrna Beach, FL 

Snowbirds can flock to Florida to escape the ice, snow, and freezing temperatures in the North. On New Smyrna Beach, the temperatures drop to the low 50s. During the day, the weather is still warm enough to enjoy outdoor activities on the beach without the hassle of snow! If you prefer, you could also visit various museums and art galleries or stroll along Canal Street. 

Stay at Black Dolphin Inn

Revel in the old-world Spanish Isle architecture at Black Dolphin Inn! Stay hidden by palm trees on the banks of the Atlantic Intracoastal Waterway. Choose between 14 different luxurious rooms, each uniquely designed with vintage furnishings, inspiring artworks, eclectic accents, and spa baths.

Black Dolphin Inn

6. Norman, OK 

Couples can take advantage of a wide variety of winter activities while on vacation in Norman, OK. If you’re visiting around the holidays, be sure to check out the DownsFamily Christmas light displays. On the second Friday of each month, you can take in the local art scene and take part in the art walk. You might also enjoy the Winter Wind Concert Series, Annual Chocolate Festival, Second Sunday Poetry Reading, and more! 

Stay at Montford Inn 

Find luxurious yet comfortable accommodations at Montford Inn, a Prairie-style property in the heart of Norman Oklahoma’s Historic District. Escape from the hustle and bustle of everyday life and just enjoy the company of your sweetheart in this romantic setting.

Montford Inn

7. Humboldt, TN

Stay at Magnolia Manor and Chapel

Magnolia Manor and Chapel is an elegant six-room bed & breakfast and wedding venue located in West Tennessee. Being in a small town, our bed and breakfast gives our guests a relaxing getaway with a southern and soulful feel. Our 1895 historic chapel is a unique venue with original 125-year-old hand-carved pews and stunning arched windows.

Magnolia Manor

Stay Select

While researching some of the most romantic winter weekend getaways for couples, consider booking a stay at one of our quality-assured properties! Our esteemed collection of award-winning bed and breakfasts, inns, boutique hotels, lodges, and luxury cabins set the scene for an unforgettable experience. Maybe you’ve always wanted to stay in a stately mansion. Perhaps you’d prefer to retreat to a countryside farmhouse. Regardless of the type of lodging you’d prefer, you can rest assured that you’re in trusted hands at a Select Registry property. 

Browse Our Property Map 

Best Places to Stay in Cleveland

j palen house Retreat
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j palen house
jpalen house Roost Private Courtyard
J Palen House Retreat Spa Bath
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j palen house Roost Loft
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Sleep Inn...Dine Out

J Palen House

Cleveland, OH

Best Places to Stay in Humboldt

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Magnolia Manor and Chapel

Humboldt, TN

Best Places to Stay in Louisville

Chateau Bourbon Exterior
Chateau Bourbon glass
Bedding with pillows at Chateau Bourbon
Chateau Bourbon interior
Innkeepers at Chateau Bourbon
Innkeepers Missy & John Hillock
Cocktail & Dessert
Waffle with bourbon buttered maple syrup
Bourbon selection
Angel's Share suite
Reserve suite
Single Barrel suite
Stillhouse suite
Sleeping porch

Chateau Bourbon

Louisville, KY

Best Places to Stay in McMinnville

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Youngberg Hill
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guest room with a view
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wine and view
Couple Dining
Youngberg Hill
Youngberg Hill Cat in foreground
Youngberg Hill Vineyard
Youngberg Hill view of landscape

Youngberg Hill

McMinnville, OR

Front view of A' Tuscan Estate with porch lights on.
Napoli Guest Room
Portofino Guest Room
Tuscan Suite view from the entry door. Sitting area, fireplace and king bed.
Stairway between first and second levels.
Summer view of A' Tuscan Estate sign with hanging flower baskets and the Estate in the background.
Siena Guest Room Bathroom
Living Room
Tuscan Suite Guest Room
Portofino Guest Room Bathroom
Tuscan Suite Bathroom
Vineyard view with Barn in background

A' Tuscan Estate Bed & Breakfast

McMinnville, OR

Best Places to Stay in New Smyrna Beach

couple by fireplace looking at water views
Black Dolphin InnFlorida
bedroom with view of water
Black Dolphin InnFlorida
Black Dolphin InnFlorida
Black Dolphin InnFlorida
bedroom with view of water

Black Dolphin Inn

New Smyrna Beach, FL

Best Places to Stay in Norman

Montford inn cottages Spring exterior
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front porch
bedroom with fireplace
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Montford inn cottages Interior2
Montford inn exterior
front porch

Montford Inn and Cottages

Norman, OK

Best Places to Stay in Sunderland

sagra hill farm
sagra hill farm
sagra hill farm
sagra hill farm
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sagra hill farm
hill farm fireplace
hill farm llamas
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picking apples
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swing in front

Hill Farm Inn

Sunderland, VT

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