Pittsfield Hotels from S$150

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Check prices for these dates

Tonight
22 Feb - 23 Feb
Tomorrow
23 Feb - 24 Feb
Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar

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Top 10 trending Pittsfield hotels

Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (28)
"Good ownership, very helpful"
The price is S$365
includes taxes & fees
2 Mar - 3 Mar
Stay At Jimmy's
The Shire Woodstock
Property grounds

The Shire Woodstock

3.0 star property
8.8 out of 10, Excellent, (727)
"We spend a weekend at the shire every winter and absolutely love it! It’s walkable to the heart of Woodstock, close to Killington, and even allows us to bring our dog! Can’t wait for next year!"
The price is S$243
includes taxes & fees
24 Feb - 25 Feb
The Shire Woodstock
The Vesper
Individually decorated, individually furnished, free WiFi, bed sheets

The Vesper

3.0 star property
9.6 out of 10, Exceptional, (15)
"Charming inn, great service"
The price is S$207
includes taxes & fees
25 Feb - 26 Feb
The Vesper
Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (501)
"Great resort, beautiful property-only issue was room was cold - aside from that, loved the stay "
The price is S$498
includes taxes & fees
16 Mar - 17 Mar
Woodstock Inn & Resort
The Jackson
Fireplace

The Jackson

4.0 star property
10.0 out of 10, Exceptional, (204)
"Very comfortable accommodations, and incredibly friendly and helpful staff. It was great to have coffee/tea available anytime and we spent lots of time by the cozy fire. "
The price is S$328
includes taxes & fees
2 Mar - 3 Mar
The Jackson
506 On the River Inn
Private kitchen

506 On the River Inn

4.0 star property
9.4 out of 10, Exceptional, (964)
"It’s been our second time going to On the River Inn VT and we’ve been amazed both times we went there! The view of the lake/courtyard is beautiful and the hotel in general is very clean. My daughter loved the pool and the game room. The staff were very helpful with everything we asked for and the breakfast was top notch. Definitely worth the trip!"
The price is S$307
includes taxes & fees
3 Mar - 4 Mar
506 On the River Inn
Sleep Woodstock Motel
Individually decorated, desk, blackout curtains, iron/ironing board

Sleep Woodstock Motel

2.0 star property
9.6 out of 10, Exceptional, (463)
"Sleep Woodstock is a great economic option to stay when visiting the Killington Ski Mountain. It’s only 15 minutes away and convenient to get to. Sleep Woodstock is also very close to Woodstock with its great option for dinning no shopping. The room was also clean and new. The Sleep Woodstock team also kept the parking area plowed and easy to access even during a huge snow storm. Kudos to everyone."
The price is S$150
includes taxes & fees
3 Mar - 4 Mar
Sleep Woodstock Motel
Echo Lake Inn
Exterior

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (94)
"Old fashioned inn with wonderful hosts."
The price is S$369
includes taxes & fees
25 Mar - 26 Mar
Echo Lake Inn
My Place Hotel-Randolph VT
Full-sized fridge, microwave, stovetop, coffee/tea maker

My Place Hotel-Randolph VT

2.0 star property
9.4 out of 10, Exceptional, (137)
"Dillon was exceptional during the check in and immediately addressed our concerns. He was very informative and pleasant. The room is clean & modernly updated. "
The price is S$202
includes taxes & fees
28 Feb - 1 Mar
My Place Hotel-Randolph VT
Turn of River Lodge
Interior

Turn of River Lodge

2.5 star property
9.0 out of 10, Wonderful, (244)
"This was such a cozy lodge! They provided a complimentary breakfast with plenty of pastries, bread, coffee, water, orange juice & cereal. It was super convenient that breakfast was ready by 6:30am, which was perfect timing for us to eat before hitting the slopes by 8am! This is a shared lodge, so there is a main room on the first floor with large tables & couches in front of a fireplace where you can lounge & mingle with others. Just a heads up, if you don't want to share a bathroom, make sure...
The price is S$194
includes taxes & fees
26 Feb - 27 Feb
Turn of River Lodge
Fall Line Condo D1 1 Bedroom Condo
Exterior

Fall Line Condo D1 1 Bedroom Condo

3.5 star property
The price is S$678
includes taxes & fees
2 Mar - 3 Mar
Fall Line Condo D1 1 Bedroom Condo
Fall Line Condos by Killington VR - 3 Bedrooms
Interior

Fall Line Condos by Killington VR - 3 Bedrooms

3.5 star property
The price is S$1,065
includes taxes & fees
27 Feb - 28 Feb
Fall Line Condos by Killington VR - 3 Bedrooms
Fall Line Small Studio - Perfect For Two - On Shuttle Route W/ Amenities G6a 1 Bedroom Condo
Exterior

Fall Line Small Studio - Perfect For Two - On Shuttle Route W/ Amenities G6a 1 Bedroom Condo

2.0 star property
The price is S$403
includes taxes & fees
27 Feb - 28 Feb
Fall Line Small Studio - Perfect For Two - On Shuttle Route W/ Amenities G6a 1 Bedroom Condo
Beautiful 2br/2ba Fall Line Condo W/ Mountain Views, Pool, Hot Tub, Sauna, Shuttle. G6b 2 Bedroom Condo
Exterior

Beautiful 2br/2ba Fall Line Condo W/ Mountain Views, Pool, Hot Tub, Sauna, Shuttle. G6b 2 Bedroom Condo

3.5 star property
The price is S$835
includes taxes & fees
27 Feb - 28 Feb
Beautiful 2br/2ba Fall Line Condo W/ Mountain Views, Pool, Hot Tub, Sauna, Shuttle. G6b 2 Bedroom Condo
Fall Line Condos by Killington VR - 1 Bedrooms
Interior

Fall Line Condos by Killington VR - 1 Bedrooms

3.5 star property
The price is S$859
includes taxes & fees
23 Feb - 24 Feb
Fall Line Condos by Killington VR - 1 Bedrooms
Killington Mountain Lodge, Tapestry Collection by Hilton
Terrace/patio

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 star property
7.2 out of 10, Good, (1001)
"Great place, helpful staff! However, miscommunication with the bus schedule… make sure to stand on correct side of road when using bus* "
The price is S$290
includes taxes & fees
25 Mar - 26 Mar
Killington Mountain Lodge, Tapestry Collection by Hilton
Whitetail Chalet 4 Bedroom Home
Outdoor spa tub

Whitetail Chalet 4 Bedroom Home

3.0 star property
The price is S$1,517
includes taxes & fees
24 Feb - 25 Feb
Whitetail Chalet 4 Bedroom Home
The Tanglewood Lodge: Amazing Ski Home For Groups. Hot Tub. Close To Killington Resort! 4 Bedroom Home
Outdoor spa tub

The Tanglewood Lodge: Amazing Ski Home For Groups. Hot Tub. Close To Killington Resort! 4 Bedroom Home

3.0 star property
The price is S$1,629
includes taxes & fees
6 Mar - 7 Mar
The Tanglewood Lodge: Amazing Ski Home For Groups. Hot Tub. Close To Killington Resort! 4 Bedroom Home
Killington Grand Hotel
Exterior

Killington Grand Hotel

3.5 star property
8.8 out of 10, Excellent, (172)
"Great hotel very child and family friendly"
The price is S$743
includes taxes & fees
4 Mar - 5 Mar
Killington Grand Hotel
Mountain Green Condo 1B9 1 Condo
Living area

Mountain Green Condo 1B9 1 Condo

3.5 star property
The price is S$663
includes taxes & fees
9 Mar - 10 Mar
Mountain Green Condo 1B9 1 Condo
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 14.4 mi (23.2 km) from the heart of Pittsfield, Comfort Inn Rutland - Killington is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Killington Mountain Lodge, Tapestry Collection by Hilton and My Place Hotel-Randolph VT. See all available top hotels, or 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 place to stay on a budget in Pittsfield?

Based on reviews, Clear River Inn is a popular inn for our travellers who want a more economical choice, and features free WiFi and free parking. View all budget hotels 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?

Comfort Inn Rutland - Killington: Features buffet, an indoor pool and free self parking. Days Inn by Wyndham Rutland/Killington Area and Woodstock Inn & Resort are a couple of other choices that feature an on-site pool. View all hotels with pools in Pittsfield.

What is the best spa hotel in Pittsfield?

Sweet Life - Vermont Chalet - 6 Person Indoor Hot Tub - 15 min to Killington is a top spa hotel with an arcade/games room, barbecues and billiards/pool table. Kick back and relax in the hot tub. Other popular spa hotels in Pittsfield include Newly Built Killington Vermont Ski House and Sweet Life - GetAway.

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. A top sight in the area is Killington Resort. In Pittsfield, there are 40 hotels and other accommodation options to choose from. Find out more about Pittsfield.

What are the top places to visit in Pittsfield?

A favourite place to visit is Green Mountain National Forest. Additionally, you'll find Killington 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.