10 Best Hotels in Woodstock VT: Where to Stay in 2023

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Are you planning a trip to beautiful Woodstock, Vermont? We can help with that!

Woodstock is such a lovely town, and its got quite a lot going on: delicious restaurants, close proximity to some of the best fall foliage and winter sports spots, and oh my goodness, have you seen Woodstock at Christmastime? It’s like something out of a Hallmark movie!

There are so many options for where to stay in this area, including elegant inns, charming B&Bs, and gorgeous hotels in Woodstock VT and beyond.

Whether you’re looking to splurge on swoon-worthy luxury accommodations or you’d like to check out more budget-friendly options, there’s something for you on this list of the best hotels in Woodstock, Vermont!

Don’t have time to read the whole post? These are our top recommendations:

🍁Best Luxury Hotel in Woodstock: Woodstock Inn & Resort

🍁Best Family-Friendly Woodstock Hotel: 506 on the River Inn

🍁Best Budget-Friendly Woodstock Hotel: Sleep Woodstock Motel

Best Hotels in Woodstock VT

Woodstock Inn and Resort

Very large white building with an expansive lawn outside in Woodstock Vermont
One of the most popular hotels in Woodstock VT, Woodstock Inn & Resort is stunning!

Known as “Vermont’s Most Beautiful Address,” Woodstock Inn and Resort is one of the best hotels in Woodstock VT for those looking for a little luxury and pampering during their visit. Rooms are tastefully decorated with a sensible Vermont elegance, and generously appointed with thoughtful amenities like scrumptious chocolates and a candle for added comfort and coziness.

Voted one of the top resorts in the Northeast in Condé Nast, there’s more to this Woodstock inn than just gorgeous rooms! Visitors love the Woodstock Inn & Resort full-service spa and the onsite dining options; Red Rooster is a AAA Four Diamond-rated that is a must-visit restaurant in Woodstock.

Oh, and if you’re looking for pet friendly hotels in Woodstock VT, they offer pet friendly room options, too!

14 The Green, Woodstock, Vermont 05091

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The Woodstocker B&B

When you think charming Vermont bed and breakfasts, you’re likely thinking of places like The Woodstocker B&B! Offering an elevated bed and breakfast experience, this Woodstock B&B is known for its historic charm (hello, original wooden floors!), fantastic location, and the warm hospitality of its hosts.

There are only 9 guestrooms to choose from and they do book up quickly, so this isn’t a last-minute option for where to stay in Woodstock VT, by any means. In-room amenities offered include twin clawfoot soaking tubs, infrared saunas, and more, so be sure to specify which calls to you when you book.

The Woodstocker B&B requires all guests be 16 and up, so this isn’t a place to stay with kids. It is a very popular Woodstock B&B for couples trips, and guests absolutely love that they can have their cooked-to-order breakfast in one of the shared common areas or in their rooms; breakfast in bed is always a nice touch on a romantic getaway!

61 River St, Woodstock, VT 05091

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506 on the River Inn

I recently stayed at 506 On the River Inn, so you can read my full review here.

Located near the lovely Ottaquechee River, 506 on the River Inn is as scenic on the outside as it is on the inside!

All guestrooms are beautifully furnished with gorgeous detail, but rooms in the main hotel offer scenic river views and their own private balconies and patios, too.

506 on the River is one of the top hotels in Woodstock VT for families to stay, with a fully stocked game room for the big kids and a toddler play area for the smaller kiddos, a beautiful indoor pool, sauna, and onsite dining.

506 Bistro & Bar is one of the most popular restaurants in Woodstock. Guests rave about the complimentary country breakfast, too!

Oh, and guess what? 506 on the River is a pet-friendly Woodstock hotel, too!

1653 W Woodstock Rd, Woodstock, VT 05091

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Fat Sheep Farm

Wooden modern house with a black roof half-covered in sunshine. The sky is blue and cloudy.

If it’s a unique place to stay you’re looking for, Fat Sheep Farm is it! While technically about a 20-minute drive outside of Woodstock, this is one of the coolest places to stay in Vermont. We got to stay here a few years back and it was fantastic!

Man and woman sitting outdoors looking at the mountains in the distance under a blue cloudy sky. They are sitting in yellow outdoorsy chairs.
Just enjoying the scenery of this gorgeous property!

Our Vermont farm stay included so much farm fun, like milking the sheep and collecting fresh eggs from the hens. It was so cool to get a little taste of life on a Vermont farm! We stayed in one of the cute and comfy cabins at Fat Sheep Farm, and delightful touches like fresh baked blueberry scones upon arrival really make this such a sweet and unique place to stay near Woodstock.

122 Best Rd, Windsor, VT 05089 

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The Village Inn of Woodstock

One of the most darling bed and breakfasts in Woodstock, Vermont, The Village Inn of Woodstock is an absolute visual delight. This grand old Victorian has been magnificently kept, and the furnishings and decor onsite are a perfect blend of historical and contemporary touches.

Rooms at this Woodstock inn are comfortably cozy, with options for fireplaces and balconies. Guests especially love the location, as there are many fun Woodstock things to do within walking distance of this lovely inn; if you’d rather stay onsite, there also happens to be a cozy little tavern right downstairs!

41 Pleasant Street, Woodstock, VT 05091

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Jackson House Inn

Looking for a picturesque bed and breakfast in Woodstock, Vermont? Definitely check out Jackson House Inn. With an elegant, updated farmhouse aesthetic, the modern white picket fence and roomy front porch welcome guests in right from the start!

There are a variety of different guest rooms at Jackson House Inn to choose from, with all one-room suites featuring fireplaces. The grounds are so gorgeous at this Woodstock B&B, guests love strolling the beautifully landscaped space, and the pretty pond is a popular photo spot!

Visitors especially enjoy the scrumptious two-course breakfast served each morning.

43 Senior Lane, Woodstock, VT 05091

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Sleep Woodstock Motel

Motel sign for Sleep Woodstock Motel with American flag attached next to a road with green grass all around
One of our favorite places to stay in Woodstock, Vermont!

Looking for a fantastic, more budget-friendly hotel in Woodstock? Sleep Woodstock Motel delivers! We were lucky enough to stay here on one of our Woodstock trips and we absolutely loved our stay.

Smiling girl lying on a white bedspread in Woodstock Vermont
No complaints whatsoever about the comfiness of the bed at this Woodstock motel!

Rooms are modern and well appointed with extra comfy beds, and we loved the 1950s motor lodge meets modern hotel vibes. Plus, staff is fantastic. We highly recommend it to anyone looking for affordable hotels in Woodstock VT!

4324 West Woodstock Road, Woodstock, VT 05091

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The Shire

The Shire is located in town right along the scenic Ottauquechee River, so if you’re looking for riverside hotels in Woodstock, Vermont, add this one to the list! In fact, you can request one of their riverside rooms for spectacular balcony views of the river.

In addition to river view rooms, you can also request a room with a fireplace for a little added coziness on those cool Vermont nights at The Shire Woodstock. There are also lovely sitting areas on the porch and down by the river to rest and enjoy your complimentary coffee and tea with a view!

46 pleasant st, Woodstock, VT 05091

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The Vesper

Located right off the Village Green, The Vesper is one of the best places to stay in Woodstock VT for those who like to be right in the action, so to speak. Bright and colorful, the decor at The Vesper manages to be eclectic, elegant, modern, and historic all at once.

Rooms are comfortable and spacious, with options for fireplaces, jacuzzi tubs, and balconies. Guests love the daily breakfast offerings and the super convenient location of this adorable Woodstock B&B!

21 Pleasant St, Woodstock, VT 05091

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Lincoln Inn & Restaurant at the Covered Bridge

What says Vermont charm more than a covered bridge? Well, perhaps a VT covered bridge with a darling inn and award-winning restaurant just up the road? The Lincoln Inn & Restaurant at the Covered Bridge is one of the most popular places to eat and stay in Woodstock!

Rooms are the epitome of rustic New England charm, with traditional decor that is comfortable and cozy. As lovely as the inn and its grounds are – and they really are! – the true star of the show here is likely the highly lauded restaurant that has been the recipient of many, many accolades over the years!

2709 W. Woodstock Road Route 4, Woodstock, VT 05091 

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Don’t let the size of this quaint little town fool you… there’s so much to do and see and so many beautiful inns, B&Bs, hotels, and motels in Woodstock VT to choose from!

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