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The Charleston House

21 Pleasant St, Woodstock, VT 05091-1111
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Prices are the average nightly price provided by our partners and may not include all taxes and fees. Taxes and fees that are shown are estimates only. Please see our partners for more details.
Traveler (45)
Room & Suite (11)
Dining (3)


#9 of 16 B&Bs / Inns in Woodstock
Set amid the ambiance and historic tradition of the village, A part of what makes Woodstock special. Walk to surrounding art galleries, museums, shops and Vermont's National Park. Comfort and warm hospitality. Period antiques, fine reproductions, an eclectic selection of art, and Oriental rugs. 9 rooms, all with private bath. Some rooms with TV, fireplace and jacuzzi tub. Sumptuous candlelit breakfasts. Air-conditioning. Free wi-fi. Close to ski areas, golf courses, and Dartmouth College.
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Property amenities
Free parking
Free High Speed Internet (WiFi)
Free breakfast
Bar / lounge
Non-smoking hotel
Shared lounge / TV area
Clothes dryer
Room features
Air conditioning
Clothes rack
Wake-up service / alarm clock
Bath / shower
Complimentary toiletries
Hair dryer
Room types
Non-smoking rooms
Family rooms
Good to know
Centrally Located
Languages Spoken
English, German
186Reviews0Q+A33Room tips
Traveler rating
  • 151
  • 27
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Popular mentions
emw1002019 wrote a review Feb 2020
5 contributions
My husband and I stayed here for a long weekend over his birthday. We had an amazing stay! I'll start with the room. The Pomfret Hills room was on the 2nd floor in the front of the house, had 2 sets of windows that let the light in, and was just huge! The bed was comfortable, and the connected bathroom was large and supplied with amenities. The photos of this room on their website do NOT do it justice! Next - the breakfasts!! Oh my god! The hosts, Dixi and Willa, certainly don't let you go hungry. Both Saturday and Sunday's breakfast consisted of a large wedge of either a frittatta-like egg bake, sausage or bacon, fresh fruit, freshly made muffins or rolls, orange juice, and endless coffee. We ate around 9:30am on Saturday morning and ended up canceling our lunch plans because we were both still so full! Lastly, the hosts. Willa and Dixi were welcoming and accommodating beyond expectation. They engaged in conversation at breakfast and were available for questions and recommendations. This was the FIRST time that my husband and I had stayed in Woodstock, and our first time every staying in a B&B. We typically travel to the Burlington area and stay in the Hilton, so this was a great experience!
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Date of stay: February 2020
JoanW wrote a review Feb 2020
2 contributions1 helpful vote
What a treasure! The Charleston House's Dixi and Willa provided us with a wonderful and completely relaxing stay. Comfortable surroundings, delicious breakfasts and hospitality at a level that we have never experienced. It was a mini-vacation that was long overdue, and we were sad to have to leave!
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Date of stay: February 2020
Mikayla P wrote a review Jan 2020
4 contributions
Our stay at the Charleston House was simply wonderful. Photos on their website don't do this place justice, it's adorable. We stayed in the Mt. Peg room at the back of the B&B and couldn't have asked for a better room. It was spacious, comfortable and included a gorgeous four-post bed, jacuzzi tub and cozy gas fireplace. The B&B is within perfect walking distance of everything in Woodstock, including great restaurants and Mt. Tom. Our hosts were lovely, welcoming, helpful and accommodating (and they have the sweetest dog)! If you don't see something you need, just ask! They were happy to help. The breakfast was also outstanding. Included with our stay, there were three sittings (7:30, 8:30 and 9:30). At each sitting, guests gather in the formal dining room around a large, beautifully set table and share a big breakfast which can be modified upon request. An array of fresh fruit, croissants, sausage and an omelet filled each plate and orange juice and bottomless coffee filled our cups. Everything was delicious and sharing our meal with other guests was a wonderful, homey addition to our stay. We will certainly be making another reservation at the Charleston House!
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Date of stay: January 2020Trip type: Traveled as a couple
CWright wrote a review Dec 2019
2 contributions1 helpful vote
We had a fantastic stay at the Charleston House. The owners, Willa and Dixie, were so welcoming and friendly. We stayed in the "B & B" room, which was fantastic and had its own fireplace. We let them know there would be 3 of us and they had pre-made the pullout couch for us, which was a nice touch since we were coming in late! In the morning, we had a homemade breakfast, served on a beautiful table that we enjoyed with some of the other guests. So cute and friendly!!
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Date of stay: December 2019
1 Helpful vote
Katharine F. wrote a review Dec 2019
1 contribution
We loved the historic charm of this well-kept beautiful home turned inn. The hosts are wonderful and the breakfast is delicious. Our room was pretty with a very comfortable bed and spacious bathroom. Very clean and tidy. Elegant antique furnishings. You can walk right into the village and to local hiking trails.
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Date of stay: December 2019Trip type: Traveled as a couple
$181 - $270 (Based on Average Rates for a Standard Room)
United StatesVermontWoodstock
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Frequently Asked Questions about The Charleston House
Which popular attractions are close to The Charleston House?
Nearby attractions include Marsh - Billings - Rockefeller National Historical Park (0.3 miles), FH Gillingham & Sons General Store (0.2 miles), and Collective, the art of craft (0.2 miles).
What are some of the property amenities at The Charleston House?
Some of the more popular amenities offered include free wifi, free breakfast, and a lounge.
What food & drink options are available at The Charleston House?
Guests can enjoy free breakfast and a lounge during their stay.
Is parking available at The Charleston House?
Yes, free parking is available to guests.
What are some restaurants close to The Charleston House?
Conveniently located restaurants include Mangalitsa, The Prince and the Pauper, and Melaza Bistro.
Is The Charleston House located near the city center?
Yes, it is 0.2 miles away from the center of Woodstock.
Which languages are spoken by the staff at The Charleston House?
The staff speaks multiple languages, including English and German.
Are there any historical sites close to The Charleston House?
Many travelers enjoy visiting Billings Farm & Museum (0.5 miles), Marsh - Billings - Rockefeller National Historical Park (0.3 miles), and FH Gillingham & Sons General Store (0.2 miles).