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Our top choices for Pittsfield hotels

Lincoln Inn & Gallery

Lincoln Inn & Gallery
3.0 star property
West Woodstock
8.8 out of 10, Excellent, (68 reviews)
"Peaceful, historic property with amiable keepers."
United States
Elisabeth
The price is £119
includes taxes & fees
12 May - 13 May
Lincoln Inn & Gallery

Green Trails Inn

Green Trails Inn
3.0 star property
Brookfield
10.0 out of 10, Exceptional, (1 review)
"Historical charm combined with Immaculate style—- killer food hospitality highly recommend this place—- so wonderful"
United States
Christine
The price is £94
includes taxes & fees
20 May - 21 May
Green Trails Inn

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (441 reviews)
"Great location for us when visiting VT."
United States
Jeannine
The price is £79
includes taxes & fees
26 May - 27 May
My Place Hotel-Randolph VT

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (576 reviews)
"Quiet, well kept, comfortable, convenient."
United States
Elisabeth
The price is £102
includes taxes & fees
14 May - 15 May
Sleep Woodstock Motel

Middlebury Sweets Motel

Middlebury Sweets Motel
2.5 star property
Middlebury
8.6 out of 10, Excellent, (397 reviews)
"The staff was wonderful and communicated well. The connection to the candy shop and uniqueness of the motel was adorable. The outside needs some updating but the rooms were nice. We enjoyed our stay, thank you! "
United States
Sami
The price is £97
includes taxes & fees
7 May - 8 May
Middlebury Sweets Motel

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (279 reviews)
"Easy Check-In; Lovely Room; Great Location & Atmosphere. The staff was very friendly,"
United States
Michael
The price is £146
includes taxes & fees
7 May - 8 May
The Jackson

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.6 out of 10, Exceptional, (212 reviews)
"A great place to stay just away from the busier ski area. "
United States
Thomas
The price is £134
includes taxes & fees
14 May - 15 May
Mountain Meadows Lodge

The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (1,003 reviews)
"Always love our stay - dog friendly and people friendly!"
United States
Hanna
The price is £114
includes taxes & fees
13 May - 14 May
The Mountain Inn at Killington

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (923 reviews)
"Everything was great."
United States
Sue
The price is £108
includes taxes & fees
25 May - 26 May
The Shire Woodstock

Mountain Sports Inn

Mountain Sports Inn
2.0 star property
Killington
8.8 out of 10, Excellent, (1,003 reviews)
"Great place"
United States
Peter
The price is £88
includes taxes & fees
24 May - 25 May
Mountain Sports Inn

Emrose Luxury Cabins

Emrose Luxury Cabins
2.0 star property
Brandon
9.0 out of 10, Wonderful, (93 reviews)
"Will definitely be back!! "
United States
Steevyann
The price is £135
includes taxes & fees
10 May - 11 May
Emrose Luxury Cabins

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (624 reviews)
"A great and charming place to stay. "
United States
Kurt
The price is £89
includes taxes & fees
17 May - 18 May
Brandon Inn

Inn at Neshobe River

Inn at Neshobe River
3.0 star property
Brandon
9.4 out of 10, Exceptional, (16 reviews)
"Great little BAnd B just outside town. Shares property with a brewery and also offers a small food menu for dinner Fantastic view of the golf course 5 th hole Great hospitality and crazy good breakfast "
United States
Keith
The price is £142
includes taxes & fees
17 May - 18 May
Inn at Neshobe River

Killington Haus

Killington Haus
2.0 star property
Killington
9.2 out of 10, Wonderful, (41 reviews)
"Very close to ski resort, 3-minute drive, and close to restaurants on Killington Road."
United States
Alex
The price is £102
includes taxes & fees
27 May - 28 May
Killington Haus

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (1,002 reviews)
"We had a great stay, very clean and the staff was friendly! "
United States
Jordyn
The price is £121
includes taxes & fees
27 May - 28 May
Hampton Inn Rutland

Après Inn Killington

Après Inn Killington
2.0 star property
Killington
9.4 out of 10, Exceptional, (188 reviews)
"Location is great"
United States
Lei
The price is £112
includes taxes & fees
10 May - 11 May
Après Inn Killington

The Vesper

The Vesper
3.0 star property
Woodstock
9.4 out of 10, Exceptional, (60 reviews)
"This was the cutest little bed and breakfast. The staff was lovely, the check-in was easy, and we had a great time in Woodstock! "
United States
Melissa
The price is £127
includes taxes & fees
10 May - 11 May
The Vesper

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,005 reviews)
"Clean room, friendly staff, family-friendly. "
United States
Suwei
The price is £182
includes taxes & fees
27 May - 28 May
On The River Inn

Greenbrier Inn

Greenbrier Inn
2.0 star property
Killington
9.4 out of 10, Exceptional, (680 reviews)
"Great ski hotel. "
United States
Nikolai
The price is £143
includes taxes & fees
10 May - 11 May
Greenbrier Inn

The Vermont Inn

The Vermont Inn
3.0 star property
Rutland
9.2 out of 10, Wonderful, (428 reviews)
"Clean room | Hot tub | Pet-friendly "
United States
Shanshan
The price is £157
includes taxes & fees
7 May - 8 May
The Vermont Inn
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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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 £79 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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