Pittsfield Hotels from S$143

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Top 10 trending Pittsfield hotels

The Getaway 4 Bedroom Home

3.0 star property
The price is S$938
includes taxes & fees
24 Jun - 25 Jun
The Getaway 4 Bedroom Home

Serene Architect-designed Vermont Chalet 4 Bedroom Home

3.5 star property
The price is S$1,073
includes taxes & fees
22 Jun - 23 Jun
Serene Architect-designed Vermont Chalet 4 Bedroom Home

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (31)
"Jimmy and John were amazing hosts! Very communicative!"
The price is S$282
includes taxes & fees
30 Jun - 1 Jul
Stay At Jimmy's

The Shire Woodstock

3.0 star property
8.8 out of 10, Excellent, (759)
"Location was excellent "
The Shire Woodstock

The Vesper

3.0 star property
9.4 out of 10, Exceptional, (20)
"Lovely, immaculate room - breakfast delish ! highly recommend this charming boutique hotel !"
The price is S$218
includes taxes & fees
22 Jun - 23 Jun
The Vesper

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (520)
"The Woodstock Inn is beautiful. Nice having access to the Athletic Club and a shuttle."
The price is S$664
includes taxes & fees
6 Jul - 7 Jul
Woodstock Inn & Resort

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (216)
"What a lovely place to stay. The couple that manage The Jackson are absolutely wonderful and made our stay fabulous. I would highly recommend staying here with gorgeous surroundings, charming rooms and lovely hospitality."
The Jackson

On The River Inn

4.0 star property
9.4 out of 10, Exceptional, (1000)
"Wonderful place to stay. "
The price is S$315
includes taxes & fees
29 Jun - 30 Jun
On The River Inn

Lincoln Inn & Gallery

3.0 star property
9.6 out of 10, Exceptional, (9)
"Beautiful Inn and grounds."
The price is S$315
includes taxes & fees
29 Jun - 30 Jun
Lincoln Inn & Gallery

Sleep Woodstock Motel

2.0 star property
9.6 out of 10, Exceptional, (492)
"The Sleep Woodstock Motel was a delightful choice at a bargain price. A very nice roadside motel. Creative decor, comfortable bed, pristine bathroom, friendly staff, and decent price. Would recommend! 👍"
The price is S$151
includes taxes & fees
24 Jun - 25 Jun
Sleep Woodstock Motel

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (96)
"Charming place, the food was great, rooms clean, and service was excellent"
The price is S$275
includes taxes & fees
24 Jun - 25 Jun
Echo Lake Inn

My Place Hotel-Randolph VT

2.0 star property
9.4 out of 10, Exceptional, (209)
"The hotel was new, clean and comfortable"
The price is S$227
includes taxes & fees
3 Jul - 4 Jul
My Place Hotel-Randolph VT

The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home

3.0 star property
The price is S$1,273
includes taxes & fees
22 Jun - 23 Jun
The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home

Sunrise Timberline: 3br, 2ba Ski In/ski Out Condo 3 Bedroom Condo

3.0 star property
Sunrise Timberline: 3br, 2ba Ski In/ski Out Condo 3 Bedroom Condo

Turn of River Lodge

2.5 star property
9.0 out of 10, Wonderful, (254)
"Rustic, simple, no frills ski lodge. Very friendly staff, solid breakfast and clean rooms. If you’re in town to ski, golf, or get out in the mountains, its a good option to save some dough and still be near everything."
The price is S$179
includes taxes & fees
12 Jul - 13 Jul
Turn of River Lodge

Sunrise West Glade: 3br, 3ba Ski In/ski Out Condo 3 Bedroom Condo

3.0 star property
The price is S$815
includes taxes & fees
25 Jun - 26 Jun
Sunrise West Glade: 3br, 3ba Ski In/ski Out Condo 3 Bedroom Condo

Sunrise Bear Ridge C4 4 Bedroom Condo

3.0 star property
The price is S$906
includes taxes & fees
22 Jun - 23 Jun
Sunrise Bear Ridge C4 4 Bedroom Condo

Fall Line Condo D1 1 Bedroom Condo

3.5 star property
The price is S$520
includes taxes & fees
21 Jun - 22 Jun
Fall Line Condo D1 1 Bedroom Condo

Fall Line Condo D6 3 Bedroom Condo

3.5 star property
The price is S$1,018
includes taxes & fees
21 Jun - 22 Jun
Fall Line Condo D6 3 Bedroom Condo

Fall Line Condo C3 1 Bedroom Condo

3.5 star property
The price is S$572
includes taxes & fees
30 Jun - 1 Jul
Fall Line Condo C3 1 Bedroom 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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Recent Reviews in Pittsfield

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Frequently asked questions

Where is the best place to stay in Pittsfield?

Located 17.9 mi (28.9 km) from the heart of Pittsfield, Woodstock Inn & Resort is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Comfort Inn Rutland - Killington and Killington Mountain Lodge, Tapestry Collection by Hilton. 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?

Woodstock Inn & Resort: Features a seasonal outdoor pool, an indoor pool and 4 restaurants. Comfort Inn Rutland - Killington and North Star Lodge and 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. In Pittsfield, there are 44 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, Roger Clark Memorial Central Library and Pittsfield Town Hall. You'll also find Green Mountain National Golf Course and Gifford Woods State Park 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.