A lake surrounded by autumn-colored trees and a rocky shoreline.

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Our top choices for Pittsfield hotels

1. The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (63 reviews)
"Great place to live and the owner is very friendly!"
United States
Qing
The price is £145
includes taxes & fees
22 Jun - 23 Jun
The Vesper

2. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (288 reviews)
"Everything about our stay was perfect! Couldn't be happier and will be back!"
United States
Courtney
The price is £161
includes taxes & fees
20 Jul - 21 Jul
The Jackson

3. Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (582 reviews)
"Quiet, well kept, comfortable, convenient."
United States
Elisabeth
The price is £89
includes taxes & fees
23 Jun - 24 Jun
Sleep Woodstock Motel

4. On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,002 reviews)
"Beautiful place to stay"
United States
Jeff
On The River Inn

5. The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (942 reviews)
"It was a very comfortable and nice place to stay with a lot of things within walking distance and having it next to the river was fun. They also have bonfires that you can sit by at night. It was a wonderful day."
United States
Robert
The price is £138
includes taxes & fees
8 Jul - 9 Jul
The Shire Woodstock

6. Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (49 reviews)
"Wonderful amenities, location, and team, Highly recommend and would love to stay again"
United States
Heather
The price is £207
includes taxes & fees
22 Jun - 23 Jun
Stay At Jimmy's

7. Lincoln Inn & Gallery

Lincoln Inn & Gallery
3.0 star property
West Woodstock
8.6 out of 10, Excellent, (75 reviews)
"Peaceful, historic property with amiable keepers."
United States
Elisabeth
The price is £148
includes taxes & fees
2 Jul - 3 Jul
Lincoln Inn & Gallery

8. Green Trails Inn

Green Trails Inn
3.0 star property
Brookfield
10.0 out of 10, Exceptional, (3 reviews)
"Historical charm combined with Immaculate style—- killer food hospitality highly recommend this place—- so wonderful"
United States
Christine
The price is £128
includes taxes & fees
21 Jul - 22 Jul
Green Trails Inn

9. Kedron Valley Inn

Kedron Valley Inn
3.5 star property
South Woodstock
9.0 out of 10, Wonderful, (335 reviews)
"Clean very well decorated room with comfortable beds and lots of pillows. Would stay again "
United States
Andrew
The price is £219
includes taxes & fees
1 Jul - 2 Jul
Kedron Valley Inn

10. Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (2 reviews)
"The property manager greeted us when we walked in and she was extremely friendly and kind. The inn was charming and had a homey feel, and the rooms were very clean and well maintained with awesome amenities."
United States
Sara
The price is £182
includes taxes & fees
21 Jun - 22 Jun
Deer Brook Inn

11. Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (586 reviews)
"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."
United States
Christopher
Woodstock Inn & Resort

12. My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (472 reviews)
"Great stay for passing through. It’s super clean and great dog friendly option"
United States
John
The price is £96
includes taxes & fees
12 Jul - 13 Jul
My Place Hotel-Randolph VT

13. Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (100 reviews)
"Food was excellent. Room was clean and cozy. Staff were all incredibly welcoming and friendly. Perfect location. Would highly recommend. "
United States
Danielle
The price is £166
includes taxes & fees
22 Jun - 23 Jun
Echo Lake Inn

14. The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (1,001 reviews)
"Clean, comfortable and great location. Plus they have a hotel dog on staff!"
United States
Laura
The price is £109
includes taxes & fees
28 Jun - 29 Jun
The Mountain Inn at Killington

15. Mountain Sports Inn

Mountain Sports Inn
2.0 star property
Killington
8.8 out of 10, Excellent, (1,002 reviews)
"Great place"
United States
Peter
The price is £91
includes taxes & fees
21 Jun - 22 Jun
Mountain Sports Inn

16. Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.6 out of 10, Exceptional, (230 reviews)
"Beautiful couple for hosts and stunning location. Great breakfast and hot tub to relax after a long drive. Will come back to stay longer"
Canada
Tanuja
Mountain Meadows Lodge

17. Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (25 reviews)
"I enjoy the location "
United States
troy
The price is £156
includes taxes & fees
23 Jun - 24 Jun
Mountain Green

18. Killington Haus

Killington Haus
2.0 star property
Killington
9.0 out of 10, Wonderful, (44 reviews)
"Great place!"
United States
Jack
The price is £87
includes taxes & fees
2 Jul - 3 Jul
Killington Haus

19. Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (397 reviews)
"Very convenient location with warmth and wonderful hosts."
United States
Martin
The price is £121
includes taxes & fees
22 Jun - 23 Jun
Snowed Inn

20. North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.8 out of 10, Excellent, (1,000 reviews)
"Another great stay. The hot pool is rad. It is super mega to have the bar and restaurant on-site! Staff are always friendly and helpful."
United States
patrick
The price is £110
includes taxes & fees
22 Jun - 23 Jun
North Star Lodge and Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Stay near popular Pittsfield attractions

Learn more about Pittsfield

Nestled in Vermont's Green Mountains, Pittsfield offers excellent hiking on the Long Trail and thrilling mountain biking at Green Mountain Trails. Riverside picnics along the Tweed River provide peaceful breaks between seasonal activities at nearby Killington Resort.

A lake surrounded by autumn-colored trees and a rocky shoreline.

Top Pittsfield Hotel Reviews

More cheap stays in Pittsfield

Frequently asked questions

What is the best area to stay in Pittsfield?
The best area to stay in Pittsfield is right in the village centre, particularly around Main Street, as it offers the most convenient access to local amenities and the region's natural beauty.

Pittsfield's village centre is a small, picturesque area typical of rural Vermont. Main Street runs through the heart of the village, where you'll find the general store, a few local eateries, and the town hall. It's a compact and easily navigable area, providing a cosy base for exploring the surrounding Green Mountains.

Couples looking for a relaxing escape will find the village centre ideal. It offers a peaceful setting with immediate access to hiking trails and scenic drives. You can enjoy quiet evenings at local dining spots and spend your days exploring the outdoors, perhaps visiting nearby Gifford Woods State Park or taking a drive along Route 100 for stunning views.

For those planning an active holiday, staying in the village centre puts you in the superb spot for outdoor pursuits. Many accommodations offer direct access to trailheads for hiking, mountain biking, and in winter, cross-country skiing or snowshoeing.
What are the best hotels in Pittsfield that travellers recommend?
For a highly recommended hotel in Pittsfield, consider the Clear River Inn.

The 3-star Clear River Inn, with an 8.8 rating, is a popular choice among travellers. Guests frequently praise the incredible breakfast and appreciate the premium bedding provided. This inn is also ideally located for those interested in outdoor activities, with nearby options for cross-country and downhill skiing, and it offers rooms with delightful river and mountain views.
What are the top pet-friendly hotels in Pittsfield?
For a top pet-friendly hotel in Pittsfield, the Clear River Inn is an excellent choice.

This 3-star hotel, with an 8.8 rating, is praised by guests for its pet-friendly policies, welcoming dogs and providing food and water bowls. It is also a great base for outdoor enthusiasts, with cross-country and downhill skiing areas nearby. The Roger Clark Memorial Central Library is also conveniently located just under 2 kilometres away. Guests particularly appreciate the incredible breakfast.
What are the best budget hotels in Pittsfield?
For a highly-rated budget hotel in Pittsfield, consider the Clear River Inn.

The 3-star Clear River Inn, with an 8.8 rating, is an excellent choice for budget-conscious travellers. Guests frequently highlight the incredible breakfast offered. The hotel provides amenities such as free WiFi and complimentary toiletries. It also offers free self-parking, which is very convenient. For those interested in winter sports, the inn is located near areas for cross-country skiing, downhill skiing, and a general ski area. Additionally, it is close to the Roger Clark Memorial Central Library, just 1.9 km away.
What are the most romantic hotels in Pittsfield for couples?
For a romantic hotel in Pittsfield, Vermont, the Clear River Inn is an excellent recommendation for couples.

This 3-star hotel, with an 8.8 rating, offers a lovely setting with many rooms featuring mountain views, and some even include balconies or river views for a truly picturesque experience. Guests appreciate the convenience of a kitchen in their accommodation and the complimentary toiletries. It is also well-located for outdoor activities, with cross-country and downhill skiing areas nearby. Additionally, guests have frequently praised the incredible breakfast provided.
What are the best hotels in Pittsfield near Roger Clark Memorial Central Library?
For hotels in Pittsfield near Roger Clark Memorial Central Library, the Clear River Inn is a great option.

The 3-star Clear River Inn, with an 8.8 rating, is located approximately 1.9 kilometres from Roger Clark Memorial Central Library. This hotel is particularly well-suited for families who enjoy winter sports, as it is conveniently located near cross-country and downhill skiing areas. Guests appreciate the inclusion of kitchens in the accommodations, along with complimentary Wi-Fi and free toiletries. Many rooms offer pleasant mountain views, and free self-parking is available. Previous guests have often described the breakfast as incredible.
When is the best time to go to Pittsfield?
The best time to go to Pittsfield, Vermont, is during the summer (June to August) for outdoor activities or in autumn (September to October) for the stunning foliage.

Summer in Pittsfield offers warm, pleasant weather, ideal for exploring the surrounding Green Mountain National Forest. You'll find numerous hiking trails, such as those leading to the summit of Pico Peak or along the Long Trail. The White River also provides opportunities for fishing and swimming. This season is great for active travellers or couples who enjoy nature and outdoor adventures.

Autumn transforms Pittsfield into a spectacular display of reds, oranges, and yellows as the leaves change colour. The crisp air and picturesque scenery make it an excellent time for scenic drives along Route 100 or exploring local farms and craft shops. This period is particularly popular with couples seeking a romantic getaway or anyone looking for a visually stunning and relaxing escape.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Pittsfield.
How can I save on a Pittsfield hotel booking with Expedia?
Members always get our best prices. Find our best Pittsfield hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Pittsfield hotel?
Prices for hotels in Pittsfield often vary, but you can find a great deal from £87 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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