Vermont Getaway

Plan the Most Romantic Vermont Getaway of the Year

A couple holding hands and walking through town during their romantic Vermont getaway

As we welcome yet another New Year here in beautiful Vermont, it brings 12 more months of possibilities, joy, connection, adventure, and more. If you’re looking for fantastic things to do with your loved ones this year, consider planning the ultimate romantic Vermont Getaway. Though there are plenty of places to relax and unwind in the rural paradise of Vermont, there’s no better place for a romantic Vermont Getaway than the charming village of Woodstock, Vermont – and more to the point, the Jackson House Inn, which is one of the best Woodstock, VT hotels.

Woodstock is considered one of the most scenic villages in all of Vermont. Here, you’ll find an incredible array of independently owned shops that reflect the very best of Vermont’s independent spirit, along with some delightful restaurants, outstanding museums and other attractions, and, of course, the unbeatable natural beauty Central Vermont is known for. There are many great things to do in Woodstock, VT – especially if you’re here celebrating a romantic Vermont Getaway!

As delightful as the town of Woodstock is, the real reason to escape to this charming town for a romantic couple’s getaway is the chance to stay in one of the gorgeous rooms at our exquisite boutique hotel in Woodstock, VT. Romance is at the very heart of our business model, which means we know how to curate exceptional guest experiences that offer the perfect blend of welcoming hospitality and intimacy.

Whether you’re looking for a cozy place to curl up or a destination filled with fun adventures, there’s no better place to stay in Vermont than our hotel in Woodstock, VT. Book your romantic Vermont getaway with us today!

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Winter in Vermont

Experience the Best Winter in Vermont This Year

Gorgeous landcapes near Woodstock showcase the beauty of Vermont in winter

Vermont in winter is truly magical, especially when you spend it in the picturesque village of Woodstock, VT. With winter scenery that looks like something seen on a postcard, Vermont’s winter wonderland is something we think everyone should experience at least once. Whether you love snow-based sports like downhill skiing or snowboarding, cross-country skiing, or snowshoeing, or whether your idea of a winter getaway involves more time curled up in front of a fire with a good book, we’d love nothing more than to help you enjoy the best of Vermont in winter this year.

There are so many great things to do in Vermont in winter, and our upscale Woodstock, VT hotel is the perfect home base for all of it. The Jackson House Inn is located near two popular Vermont ski areas, our super local mountain, Saskadena Six, and the bigger Killington Resort – but that’s just the beginning of all the great things waiting for you in this uniquely beautiful winter paradise.

It’s hard to go wrong when visiting Vermont in winter, but it’s even better when you add a stay at the charming, luxurious Jackson House Inn, Woodstock VT’s top-rated boutique hotel. Our Woodstock, VT hotel is nestled just outside of downtown Woodstock, surrounded by the breathtaking beauty of this quaint, storybook village.

Woodstock, VT is exceptionally fun to visit year-round, but in the winter, it offers a magical winter wonderland like no other. Book a room at our Boutique Hotel in Woodstock, VT today!
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Christmas in Woodstock, Winter in Vermont

Experience the Best of a Woodstock, Vermont Christmas!

Enjoy the magical of a Woodstock, Vermont Christmas while shopping downtown, where the stores are dressed for the season

If you haven’t had the pleasure of experiencing a Woodstock, Vermont Christmas, let us introduce you to the sheer magic of the season this year. Old-fashioned holiday charm takes over the shops and businesses lining Central Street in downtown Woodstock, and holiday events keep the atmosphere bright, festive, and filled with joy. There is simply nowhere more beautiful than a Woodstock, Vermont Christmas.

Your headquarters for all things festive – not to mention romantic and relaxing – is the Jackson House Inn, the leading Woodstock, VT Hotel. We offer an intimate guest experience that remains unmatched in this storybook Vermont town. We’d love to treat you to a relaxing getaway while enjoying the best of this holiday season.

Start (or finish) your holiday shopping in beautiful downtown Woodstock, join in the festivities during the annual Wassail Weekend, participate in some authentic Victorian Christmas Traditions at The Christmas on the Farm event at nearby Billings Farm, and otherwise, treat yourself to a few days of quiet luxury at our Four Diamond Woodstock, VT Hotel this holiday season. Book your room today! Continue Reading…

Things to do in Woodstock VT, Vermont Getaway

Plan An Unforgettable Vermont Getaway This Winter

A senir couple enjoying a romantic Vermont Getaway at our Boutique hotel in Woodstock, VT

When you need a place to relax and hit the reset button this fall or winter, there’s nothing better than a Vermont getaway – and there’s truly no better place for that than one of the best hotels in Woodstock, VT, the Jackson House Inn. Our boutique hotel is the perfect place to celebrate a special occasion or spend a quiet weekend away, reconnecting with your sweetheart or gathering for a friends’ getaway.

Romance is at the heart of what we do here at our Woodstock, VT Hotel. As we continue our gradual slide into winter, there’s never been a better time to plan a Vermont getaway. The charming village of Woodstock is one of the most beautiful and well-regarded small towns in New England. It’s easy to see why, too, with plenty of fantastic shopping, spectacular artisans and makers to visit, excellent restaurants for every foodie, and all the gorgeous rural scenery and outdoor activities you crave in a Vermont getaway.

Enjoying the beautiful town of Woodstock is excellent, but that’s certainly not the only reason to plan a Vermont getaway here. The chance to stay at one of the best hotels in Woodstock, VT is more than enough reason to visit – in fact, we think it’s the best reason to visit! Our Woodstock, VT hotel offers unparalleled hospitality with easy access to the top things to do in Woodstock, VT, allowing you to enjoy your Vermont getaway in whatever way feels best.

There’s a reason we’re rated as one of the best places to stay in Vermont, and we don’t think it will take you long to see it for yourself. Book your getaway at one of the top-rated hotels in Woodstock, VT today!

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Things to do in Woodstock VT

The Best Things to do in Woodstock, VT This Fall

Gorgeous rural scenery with fall foliage - one of the best things to do in Woodstock, VT

Is there anything more spectacular than Vermont in the fall? We don’t think so, especially when you stay in a charming and breathtakingly beautiful town like Woodstock, VT! There are, of course, plenty of wonderful things to do in Woodstock, VT in the fall. However, one of the best reasons to make this your fall getaway destination is the chance to relax and unwind at the stunning Jackson House Inn.

The Jackson Inn is an exquisite boutique hotel just one mile from downtown Woodstock. We’re nestled in the quiet countryside just on the edge of town. We offer an unparalleled destination where couples love to retreat, unwind, and share some quiet, uninterrupted time. Between a stay here and time spent in what’s considered Vermont’s most beautiful village, you have the recipe for an unforgettable getaway this fall.

Whether you enjoy hiking, biking, shopping, or driving through beautiful countryside, you’ll find there are more than enough things to do in Woodstock, VT this fall. Make sure to give yourself plenty of time to soak up the experience at our elegant Vermont Bed and Breakfast – a place where you’ll feel your stress melt away from the moment you arrive. Book your room at our boutique hotel in Vermont today! Continue Reading…

Stay Local

March Maple Madness


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March has arrived and the Great Melt has slowly begun. Just last week we looked outside and saw a little blade of green grass waving in the breeze behind the Inn. It’s hard to believe the small, telltale signs of spring are starting when even now skiing is the number one pastime and nearby Killington has 110 of their runs still open. The hint of spring on the horizon has us savoring every snowy moment as our first winter in New England draws to a close.

We set foot in Vermont for the first time last summer as the new Innkeepers at the Jackson House Inn and immediately began mentally preparing for the upcoming winter months. People far and wide told us Vermont winters were nothing to be trifled with. Snow isn’t anything new to Lauren as she grew up in Colorado and spent the past seven years in Tahoe, California. Kayla, however, is an Oregonian through and through and to citizens of the Pacific Northwest, an inch of snow can be cause for a major city shut down. The transition to Vermont was even more abrupt for Kayla, coming from a sabbatical year enjoying New Zealand’s sun and beaches. But when the first snowstorm arrived and dropped 30 inches on us overnight, we were prepared for grueling days of snow management. Instead, as we shoveled our way out of the Inn the following day, we found ourselves falling in love with the winter wonderland around us. We were immediate converts, putting dreams of stand-up paddleboards and hiking shoes away and embracing Vermont Snow Activities (as we refer to them).

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Vermont Snow Activities are plentiful and diverse, and we’ve made it our goal to give each of them at least one solid attempt. Snowshoeing has been a wild success, and there seem to be never ending trail systems in the area to explore. Snowshoeing has the added benefit of keeping our dogs entertained, too, as they run by our side. Downhill skiing at Suicide Six was a favorite of Kayla’s, while Lauren was more than happy to sit at the fire pit, sip a Vermont beer, and munch on fries in the sunshine for the afternoon. Snowmobiling proved to be a wonderful way to explore a new area (although we needed hand massages after two hours of riding around with death grips on the handle bars). We took to the ice on Lake Morey to practice our triple axels and toe loops and made it about halfway around the lake before realizing we didn’t know how to do any of those fancy moves. However, the views were spectacular and ice skating in the open air on a frozen lake was a wonderful experience. The final must-do activity before the Melt is too far advanced is to grab a fishing pole and try out the noble art of ice fishing. This will be particularly entertaining because Lauren prefers her fish in a sautée pan and will be relieved if nothing actually bites.



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These excursions have made the months of snow and cold positively enchanting and we’ve been delighted to trade recommendations with new and returning guests. If you want one more shot of winter in Woodstock, we still have a few lesser-known options up our sleeves to share with you!

Along with these adventures, winter has provided some other valuable learning experiences. We’ve found ourselves asking questions we’d never thought of before: when ordering ice melt, do you order by the pound or by the ton? If there’s an early morning snowstorm, do you still put the trash bins out on the road or will that inconvenience the heroic snow plowers? Whats the deal with roof rakes? Is 30 inches of snow normal or an aberration? Thankfully, the Woodstock community is incredibly supportive and we’ve had a lot of kind, non-judgemental guidance as we navigate the rules of Vermont winter. A quick shout-out and thanks to all those who have helped “the Jackson House Girls” over the past months!

Now that March is here, we are learning that all the old adages are true. All good things must come to an end. When one door closes, another door opens. And when in Vermont, it is all about maple syrup. Snow season may be slowly winding down, but Vermont always has something fun in store. We’re fast approaching maple sugaring season and couldn’t be more excited to share it with our guests for the first time! That syrup you enjoy with your pancakes, poured over ice cream or dolloped into your coffee has a long story behind it before arriving on your table. Vermont’s maple sugar farmers have been gearing up all winter, replacing tubing, preparing lines, and tapping trees in preparation for the next month of grueling work. In the coming weeks, the temperature will reach that sweet spot of over 40 degrees during the day and below freezing at night, and the sap will start flowing!

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The West Coast never offered many opportunities to see maple sugar season in action so we again found a host of new questions: how many trees does it take to make a gallon of maple syrup? Why are there plastic tubes strung from tree to tree? What does sap even look like? In that spirit, we drove over to local sugar house Sugarbush Farm to learn more about this Vermont tradition. Sugarbush Farm’s self-guided experience through the sugar house and lovely 15-minute Maple Walk tour through the woods helped us find the answers to all of our burning questions.

We don’t want to rob you of the chance to experience the triumphant success of correctly answering the quiz cards placed along the Maple Walk, so without giving too much away we’ll each share our favorite fun fact from the day. Lauren was both impressed, and intimidated, by the long hours needed during the sap boiling process. Farmers must add more wood to the fire every 15 minutes to keep the sap boiling at just the right temperature or risk burning their entire batch. While the process is grueling, friends and family come by to hang out, exchange stories, and, most importantly, provide food, helping the time pass. Kayla thought it was crazy that it takes 40 to 50 gallons of sap to produce a single gallon of maple syrup. It gave her a new appreciation for every dollop she pours in her coffee in the morning (yes, she officially converted to the practice). With warmer days forecast for the week ahead, maple sugaring season is really just beginning and you can come experience Vermont’s springtime passion for yourselves! Now that we’re the experts, feel free to ask us for recommendations on places to visit where you can see the magic in action–and enjoy a few samples.

With spring on the horizon, there’s still time for a few downhill runs before we say a bittersweet farewell to our newfound love of Vermont in winter. A new season’s adventures lie ahead, and we’ll keep you apprised as we discover Vermont Spring Activities! Or better still, come join us at the Jackson House Inn!

Kayla & Lauren


Elevated Wine Dinner - February 22nd.

Join us for an exclusive five-course dinner with wine pairings from Keuka Lake Vineyards from the Finger Lakes Region of New York.