See all properties

The Jackson

Top rated by guests
The Jackson Bed and Breakfast in Woodstock
The Jackson Bed and Breakfast in Woodstock
The Jackson Bed and Breakfast in Woodstock
The Jackson Bed and Breakfast in Woodstock
The Jackson Bed and Breakfast in Woodstock
review stars
9.6Outstanding
(331 Ratings)
"Beautiful stay! Highly recommend this stay."
Joleen
Don't miss out! Price and availability may change
9.6 / 10
Outstanding(331 Ratings)

Bed and Breakfast in Woodstock, VT

4-Star Bed & Breakfast

Reasons to book

Guests love it hereGuests give this property a top rating
Well priced for this locationPriced under area average
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this bed and breakfast

This smoke-free bed & breakfast features a restaurant, a bar/lounge, and coffee/tea in a common area. Free WiFi in public areas and free self parking are also provided. Additionally, concierge services, a library, and express check-out are onsite.
Housekeeping is available on request.
The Jackson offers 11 accommodations with designer toiletries and complimentary toiletries. Each accommodation is individually furnished and decorated. Beds feature down comforters. 42-inch Smart televisions come with cable channels and Netflix. This Woodstock bed & breakfast provides complimentary wireless Internet access. Irons/ironing boards, hair dryers, and change of towels can be requested. Housekeeping is provided on request.
The recreational activities listed below are available either on site or nearby; fees may apply.

Amenities

Restaurant
Free Parking
Air conditioning
Non-smoking
Bathroom
Bar
Balcony/Terrace
WiFi/Internet
No pets allowed
Ski in/Ski out
Garden
Ironing facilities
Towels
Hairdryer

Map of Woodstock, VT

city location on map

Available Rooms

Ratings and reviews

9.6 / 10
Outstanding(331 Ratings)
10 / 10Outstanding·Aug 2026
Beautiful stay! Highly recommend this stay.
10 / 10Outstanding·Jul 2026
Everything was terrific! Great vibe & location.
10 / 10Outstanding·Jun 2026
Beautiful Inn with truely exellent restaraunt at the Inn. Staff are very friendly and accomodating.
5 / 10·Oct 2026
Lovely place! Easy check in and out! I will recommend it 100%
$$$$
expedia logo

FAQs

Is parking included with this bed and breakfast?

Yes, parking is listed as an amenity at The Jackson. For more information, we encourage you to contact the property about where to park.

Is there a pool at this bed and breakfast?

We didn’t find pool listed as an amenity for this bed and breakfast. It may be worth double checking if a pool is important for your stay.

Is The Jackson pet friendly?

Unfortunately, this bed and breakfast is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at The Jackson?

We found 14 amenities for this rental. This includes restaurant, free parking, air conditioning, non-smoking, and bathroom.

Explore similar stays in Woodstock

Explore all stays
9.6 / 10
Outstanding(331 Ratings)
The Jackson
Bed and Breakfast
 in Woodstock
4star
WiFi/Internet · Air conditioning · Bar

Discover the beauty of Woodstock with a stay at The Jackson, a top rated Bed and Breakfast with amenities such as Non-smoking, Air conditioning and Bar, and more.

hotelscom logo
View deal
9.4 / 10
Outstanding(990 Ratings)
On The River Inn
Hotel
 in Woodstock
4star
WiFi/Internet · Air conditioning · Pool

Business stays, family stays, couples stay, getaway vacation, and rental in Woodstock at On The River Inn for $163 for your next trip.

expedia logo
View deal
You can save with One Key
10 / 10
Outstanding(1 Rating)
Sleep Woodstock - Dog Friendly King Suite
Bed and Breakfast
 in Woodstock
2 guests · 1 bedroom · 1 bath
WiFi/Internet · Air conditioning · TV

Nestled in Woodstock, this Bed and Breakfast is perfect for your next vacation. Enjoy Sleep Woodstock - Dog Friendly King Suite's top-rated amenities, including Air conditioning, Balcony/Terrace and Cribs or cots available, and more.

vrbo logo
View deal
9.2 / 10
Outstanding(86 Ratings)
The Vesper
Bed and Breakfast
 in Woodstock
3star
WiFi/Internet · Air conditioning · Ski in/Ski out

This Bed and Breakfast for $165 in Woodstock, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

expedia logo
View deal
You can save with One Key
10 / 10
Outstanding(1 Rating)
Sleep Woodstock - Dog Friendly King Suite
Bed and Breakfast
 in Woodstock
2 guests · 1 bedroom · 1 bath
WiFi/Internet · Air conditioning · TV

Business stays, family stays, couples stay, getaway vacation, and rental in Woodstock at Sleep Woodstock - Dog Friendly King Suite for $167 for your next trip.

vrbo logo
View deal
8.6 / 10
Excellent(1,008 Ratings)
The Shire Woodstock
Hotel
 in Woodstock
3star
WiFi/Internet · Air conditioning · TV

This Hotel for $187 in Woodstock, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

expedia logo
View deal
9.4 / 10
Outstanding(990 Ratings)
On The River Inn
Hotel
 in Woodstock
4star
WiFi/Internet · Air conditioning · Pool

This inviting Hotel in Woodstock can fit your needs for many types of vacations, at $163 per night.

hotelscom logo
View deal
9 / 10
Outstanding(352 Ratings)
Kedron Valley Inn
Inn
 in South Woodstock
3star
WiFi/Internet · Air conditioning · TV

Are you ready to indulge in a relaxing getaway? Our Inn in Woodstock has everything you need for a rejuvenating stay. Treat yourself to Kedron Valley Inn's exceptional amenities, such as Non-smoking, Air conditioning and Bar.

expedia logo
View deal
You can save with One Key
10 / 10
Outstanding(1 Rating)
Sleep Woodstock - Dog Friendly King Suite
Bed and Breakfast
 in Woodstock
2 guests · 1 bedroom · 1 bath
WiFi/Internet · Air conditioning · TV

Soak up the beauty of Woodstock in our Bed and Breakfast, Sleep Woodstock - Dog Friendly King Suite. With a range of amenities such as Air conditioning, Balcony/Terrace and Cribs or cots available, you'll feel right at home.

vrbo logo
View deal
9.2 / 10
Outstanding(86 Ratings)
The Vesper
Bed and Breakfast
 in Woodstock
3star
WiFi/Internet · Air conditioning · Ski in/Ski out

Bed and Breakfast in Woodstock, for $165 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

hotelscom logo
View deal
10 / 10
Outstanding(1 Rating)
Sleep Woodstock - Dog Friendly King Suite
Bed and Breakfast
 in Woodstock
WiFi/Internet · Air conditioning · TV

Looking for the perfect place to call home during your trip to Woodstock? This Bed and Breakfast offers a comfort and style with top-notch amenities, including Air conditioning, Balcony/Terrace and Cribs or cots available, and more.

expedia logo
View deal
8.8 / 10
Excellent(1,008 Ratings)
The Shire Woodstock
Hotel
 in Woodstock
3star
WiFi/Internet · Air conditioning · TV

This attractive Hotel in Woodstock, $187 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

hotelscom logo
View deal
8 / 10
Excellent(1 Rating)
Sleep Woodstock - Dog Friendly King Suite
Bed and Breakfast
 in Woodstock
2 guests · 1 bedroom · 1 bath
WiFi/Internet · Air conditioning · TV

Looking for a Bed and Breakfast in Woodstock, this Bed and Breakfast for $167 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

vrbo logo
View deal
Sleep Woodstock - 2 Double Beds - Dog Friendly
Bed and Breakfast
 in Woodstock
4 guests · 1 bedroom · 1 bath
WiFi/Internet · Air conditioning · TV

Experience vacation in Woodstock with our Bed and Breakfast, Sleep Woodstock - 2 Double Beds - Dog Friendly. Enjoy amenities such as Air conditioning, Cribs or cots available and Free Parking, and more.

vrbo logo
View deal
10 / 10
Outstanding(1 Rating)
Sleep Woodstock - Dog Friendly King Suite
Bed and Breakfast
 in Woodstock
WiFi/Internet · Air conditioning · TV

Looking for a memorable stay in Woodstock? Our Bed and Breakfast might just be what you're looking for. Enjoy amenities including Air conditioning, Balcony/Terrace and Cribs or cots available, and more during your stay.

expedia logo
View deal
Sleep Woodstock - 2 Double Beds - Dog Friendly
Bed and Breakfast
 in Woodstock
WiFi/Internet · Air conditioning · TV

This Bed and Breakfast in Woodstock, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

expedia logo
View deal
10 / 10
Outstanding(1 Rating)
Sleep Woodstock - Dog Friendly King Suite
Bed and Breakfast
 in Woodstock
WiFi/Internet · Air conditioning · TV

Discover the beauty of Woodstock with a stay at Sleep Woodstock - Dog Friendly King Suite, a top rated Bed and Breakfast with amenities such as Air conditioning, Balcony/Terrace and Cribs or cots available, and more.

expedia logo
View deal
Sleep Woodstock - 2 Double Beds - Dog Friendly
Bed and Breakfast
 in Woodstock
4 guests · 1 bedroom · 1 bath
WiFi/Internet · Air conditioning · TV

This inviting Bed and Breakfast in Woodstock can fit your needs for many types of vacations, at $168 per night.

vrbo logo
View deal
8 / 10
Excellent(1 Rating)
Sleep Woodstock - Dog Friendly King Suite
Bed and Breakfast
 in Woodstock
2 guests · 1 bedroom · 1 bath
WiFi/Internet · Air conditioning · TV

This attractive Bed and Breakfast in Woodstock, $167 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

vrbo logo
View deal
Sleep Woodstock - 2 Double Beds - Dog Friendly
Bed and Breakfast
 in Woodstock
WiFi/Internet · Air conditioning · TV

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Woodstock, at $168 per night for your next great vacation.

expedia logo
View deal
8 / 10
Excellent(1 Rating)
Sleep Woodstock - Dog Friendly King Suite
Bed and Breakfast
 in Woodstock
WiFi/Internet · Air conditioning · TV

When traveling to Woodstock, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $167 per night.

expedia logo
View deal
9 / 10
Outstanding(352 Ratings)
Kedron Valley Inn
Inn
 in South Woodstock
3star
WiFi/Internet · Air conditioning · TV

Nestled in Woodstock, this Inn is perfect for your next vacation. Enjoy Kedron Valley Inn's top-rated amenities, including Non-smoking, Air conditioning and Bar, and more.

hotelscom logo
View deal
Sleep Woodstock - Dog Friendly King Suite
Bed and Breakfast
 in Woodstock
2 guests · 1 bedroom · 1 bath
WiFi/Internet · Air conditioning · TV

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Woodstock, at $167 per night for your next great vacation.

vrbo logo
View deal
Sleep Woodstock - 2 Double Beds - Dog Friendly
Bed and Breakfast
 in Woodstock
WiFi/Internet · Air conditioning · TV

Enjoy the best of Woodstock in our Bed and Breakfast, Sleep Woodstock - 2 Double Beds - Dog Friendly. A stunning property with amenities including Air conditioning, Cribs or cots available and Free Parking, and more.

expedia logo
View deal
8 / 10
Excellent(1 Rating)
Sleep Woodstock - Dog Friendly King Suite
Bed and Breakfast
 in Woodstock
WiFi/Internet · Air conditioning · TV

Bed and Breakfast in Woodstock, for $167 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

expedia logo
View deal
Sleep Woodstock - 2 Double Beds - Dog Friendly
Bed and Breakfast
 in Woodstock
4 guests · 1 bedroom · 1 bath
WiFi/Internet · Air conditioning · TV

Looking to create some memories in Woodstock? Look no further than our Bed and Breakfast, Sleep Woodstock - 2 Double Beds - Dog Friendly. Enjoy top-rated amenities including Air conditioning, Cribs or cots available and Free Parking, and more.

vrbo logo
View deal
Sleep Woodstock - Dog Friendly King Suite
Bed and Breakfast
 in Woodstock
WiFi/Internet · Air conditioning · TV

Bed and Breakfast in Woodstock, for $167 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

expedia logo
View deal
Sleep Woodstock - 2 Double Beds - Dog Friendly
Bed and Breakfast
 in Woodstock
WiFi/Internet · Air conditioning · TV

When traveling to Woodstock, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $162 per night.

expedia logo
View deal
You can save with One Key
Sleep Woodstock - 2 Double Beds - Dog Friendly
Bed and Breakfast
 in Woodstock
4 guests · 1 bedroom · 1 bath
WiFi/Internet · Air conditioning · TV

The best choice in Woodstock for Bed and Breakfast, for $162 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

vrbo logo
View deal
Sleep Woodstock - 2 Double Beds - Dog Friendly
Bed and Breakfast
 in Woodstock
WiFi/Internet · Air conditioning · TV

Looking for a memorable stay in Woodstock? Our Bed and Breakfast might just be what you're looking for. Enjoy amenities including Air conditioning, Cribs or cots available and Free Parking, and more during your stay.

expedia logo
View deal

Woodstock travel inspiration

Read our blog
Guides
The Best New England Glamping Destinations
Guides
Where to Go Glamping in New York State: 6 Best Destinations
Guides
The Ultimate U.S. Bucket List: Top Activities in Every State
Guides
Why You Should Visit Vermont for a Unique Fall Foliage Experience

Keep exploring