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Our top choices for Pittsfield hotels

Lincoln Inn & Gallery

Lincoln Inn & Gallery
2.0 star property
West Woodstock
8.6 out of 10, Excellent, (62 reviews)
  • cleanliness
    Lincoln Inn offers charming riverside comfort in Woodstock, with free perks to enjoy.
"The accommodations are perfect for a weekend away and less than a 20 minute drive to Killington resort!! It is a very warm and cute stay"
United States
Ronda
The price is NZ$229
includes taxes & fees
22 Feb - 23 Feb
Lincoln Inn & Gallery

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (386 reviews)
  • cleanliness
    Comfortable stay near Vermont's scenic attractions with free WiFi and parking.
"Clean room, friendly stas"
United States
Aiste
The price is NZ$173
includes taxes & fees
11 Mar - 12 Mar
My Place Hotel-Randolph VT

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (557 reviews)
  • cleanliness
    Great ski lodge with comfortable, quiet rooms just outside charming Woodstock.
"So much love and thoughtfulness was put into our room and common area. Comfy beds, little touches like free snacks and goodies and super clean room. It's also super dog friendly! There's also a fantastic little coffee stand walking distance. "
United States
JILL
Sleep Woodstock Motel

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (266 reviews)
  • cleanliness
    Colonial elegance near Union Arena with beautiful garden and evening drinks.
"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
United States
Abby
The Jackson

Mountain Valley Retreat

Mountain Valley Retreat
2.5 star property
Killington
9.6 out of 10, Exceptional, (196 reviews)
  • cleanliness
    Scenic ski retreat near Killington Resort with free gourmet breakfast daily.
"Superb stay all the way around! Mike and Barbara work very hard for their guests and it shows with all the room details and breakfast is 5 out of 5 stars everytime. Check in and out is very easy as well as parking even on snow covered days as the property is very well kept and cleared. Loved it and want to return!"
United States
Steven
The price is NZ$206
includes taxes & fees
17 Feb - 18 Feb
Mountain Valley Retreat

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (914 reviews)
  • cleanliness
    Picturesque Woodstock retreat offers free bikes, hiking trails, and winter sports.
"Wonderful place to stay!"
United States
Robin
The Shire Woodstock

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,001 reviews)
  • cleanliness
    Riverside escape with indoor pool and bistro dining just steps from Woodstock.
"Everything was amazing from the room to the pool to the restaurant and staff. "
United States
Ilana
On The River Inn

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (55 reviews)
  • cleanliness
    Enjoy a cosy Woodstock B&B with free breakfast, WiFi, and winter sports nearby.
"Charming bed and breakfast"
United States
Nicholas
The price is NZ$323
includes taxes & fees
18 Feb - 19 Feb
The Vesper

Kedron Valley Inn

Kedron Valley Inn
3.5 star property
South Woodstock
9.0 out of 10, Wonderful, (332 reviews)
  • cleanliness
    A rustic New England inn near Vermont's natural attractions offers comfort and charm.
"Clean very well decorated room with comfortable beds and lots of pillows. Would stay again "
United States
Andrew
Kedron Valley Inn

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
The price is NZ$413
includes taxes & fees
17 Mar - 18 Mar
Deer Brook Inn

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (47 reviews)
  • cleanliness
    Charming B&B in Woodstock with complimentary breakfast and perfect location.
"Wonderful amenities, location, and team, Highly recommend and would love to stay again"
United States
Heather
The price is NZ$545
includes taxes & fees
16 Feb - 17 Feb
Stay At Jimmy's

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (564 reviews)
  • cleanliness
    Elegant Woodstock retreat with golf, spa services, and idyllic central setting.
"Excellent hotel, staff well trained. "
United States
Christian
The price is NZ$636
includes taxes & fees
8 Mar - 9 Mar
Woodstock Inn & Resort

Mountain Sports Inn

Mountain Sports Inn
2.0 star property
Killington
8.8 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Modern ski lodge with convenient access to Killington Resort and trails.
"All wonderful for a two day stay!"
United States
Charles
The price is NZ$235
includes taxes & fees
24 Feb - 25 Feb
Mountain Sports Inn

Killington Haus

Killington Haus
2.0 star property
Killington
8.6 out of 10, Excellent, (13 reviews)
"Great location to ski resort and excellent Ramen restaurant on site "
United States
Kim
The price is NZ$485
includes taxes & fees
17 Feb - 18 Feb
Killington Haus

Turn of River Lodge

Turn of River Lodge
2.5 star property
Killington
9.0 out of 10, Wonderful, (282 reviews)
  • cleanliness
    Ski-in ski-out lodge near Killington Resort with complimentary breakfast.
"Great place "
United States
Matthew
The price is NZ$230
includes taxes & fees
24 Feb - 25 Feb
Turn of River Lodge

Grey Bonnet Inn

Grey Bonnet Inn
2.0 star property
Killington
7.8 out of 10, Good, (71 reviews)
  • cleanliness
    Escape to Vermont's natural beauty with hiking and mountain biking nearby.
"Good communication "
United States
Michelle
The price is NZ$299
includes taxes & fees
22 Feb - 23 Feb
Grey Bonnet Inn

Greenbrier Inn

Greenbrier Inn
2.0 star property
Killington
9.4 out of 10, Exceptional, (662 reviews)
  • cleanliness
    Enjoy mountain adventures near two Killington ski resorts with outdoor trails.
"Room and property were very clean and staff was great. Will definitely stay again!"
United States
Martin
Greenbrier Inn

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.0 out of 10, Very good, (1,002 reviews)
  • cleanliness
    Convenient Rutland retreat with indoor pool near train station and dining.
"great hotel"
United States
Shweta
The price is NZ$246
includes taxes & fees
22 Feb - 23 Feb
Comfort Inn Rutland - Killington

The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
3.5 star property
Chittenden
9.0 out of 10, Wonderful, (104 reviews)
  • cleanliness
    Ski in, ski out at this Vermont resort with direct access to mountain trails.
"Great resort "
United States
Adam
The price is NZ$469
includes taxes & fees
17 Feb - 18 Feb
The Mountain Top Inn & Resort

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (99 reviews)
  • cleanliness
    Experience rustic charm at this B&B, with tennis courts and outdoor pool.
"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 NZ$494
includes taxes & fees
2 Mar - 3 Mar
Echo Lake 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

Where is the best place to stay in Pittsfield?
Located 9.5 mi (15.3 km) from the heart of Pittsfield, Killington Mountain Lodge, Tapestry Collection by Hilton is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Best Western Inn & Suites Rutland-Killington and Comfort Inn Rutland - Killington. See all available top hotels, or vacation rentals in Pittsfield.
What are some of the best holiday rentals that Pittsfield has to offer?
Spectacular opportunity to enjoy the finest property in Killington Summit: This holiday home rental outside of Pittsfield is located in the mountains, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub. See all vacation rentals in Pittsfield.
If I need to cancel my hotel reservation in Pittsfield, will I receive a refund?
Yes, you'll find most hotel reservations are fully refundable provided that you cancel before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If your reservation is non-refundable, you might be able to still cancel and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Pittsfield.
What's the best dog-friendly accommodation option in Pittsfield?
Clear River Inn is a top dog-friendly inn, and offers a restaurant and a nightclub for its human guests. See more pet-friendly hotel accommodations in Pittsfield.
What are some accommodation options with pools in Pittsfield?
Best Western Inn & Suites Rutland-Killington: Provides buffet, a seasonal outdoor pool and free self parking. Comfort Inn Rutland - Killington and Woodstock Inn & Resort are a couple of other choices that feature an on-site pool. View all hotels with pools in Pittsfield.
How is it to stay in Pittsfield?
Visitors can enjoy all that Pittsfield has to offer, including the bars and restaurants. This city also attracts tourists with its welcoming locals. In Pittsfield, there are 42 hotels and other accommodation options to choose from. Find out more about Pittsfield.
What are the top places to visit in Pittsfield?
Favourite places to visit include Green Mountain National Forest, Pittsfield Town Hall and Roger Clark Memorial Central Library. You'll also find Gifford Woods State Park and Pico Mountain at Killington Ski Resort in the area. Take a look at what more there is to see and do in Expedia's Pittsfield guide.
What's the seasonal weather in Pittsfield?
The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -5°C. The snowiest months in Pittsfield are January, March, February and December, with each month seeing an average of 26 cm of snowfall.

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