Pittsfield Hotels from S$143

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6 Jul - 7 Jul
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7 Jul - 8 Jul
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11 Jul - 13 Jul
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18 Jul - 20 Jul

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Top 10 trending Pittsfield hotels

Serene Architect-designed Vermont Chalet 4 Bedroom Home
Terrace/patio

Serene Architect-designed Vermont Chalet 4 Bedroom Home

3.5 star property
The price is S$1,063
includes taxes & fees
7 Jul - 8 Jul
Serene Architect-designed Vermont Chalet 4 Bedroom Home
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (34)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
The price is S$349
includes taxes & fees
7 Jul - 8 Jul
Stay At Jimmy's
The Shire Woodstock
Property grounds

The Shire Woodstock

3.0 star property
8.8 out of 10, Excellent, (771)
"Great location!! Very accommodating and clean."
The Shire Woodstock
The Vesper
1 bedroom, individually decorated, individually furnished, free WiFi

The Vesper

3.0 star property
9.2 out of 10, Wonderful, (24)
"Lovely, immaculate room - breakfast delish ! highly recommend this charming boutique hotel !"
The price is S$210
includes taxes & fees
7 Jul - 8 Jul
The Vesper
Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (521)
"Relaxing "
The price is S$699
includes taxes & fees
13 Jul - 14 Jul
Woodstock Inn & Resort
The Jackson
Fireplace

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (217)
"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
Private kitchen

On The River Inn

4.0 star property
9.4 out of 10, Exceptional, (1000)
"Wonderful place to stay. "
The price is S$312
includes taxes & fees
7 Jul - 8 Jul
On The River Inn
Lincoln Inn & Gallery
Interior

Lincoln Inn & Gallery

3.0 star property
9.4 out of 10, Exceptional, (13)
"Beautiful Inn and grounds."
The price is S$166
includes taxes & fees
7 Jul - 8 Jul
Lincoln Inn & Gallery
Sleep Woodstock Motel
2 bedrooms, individually decorated, desk, blackout curtains

Sleep Woodstock Motel

2.0 star property
9.6 out of 10, Exceptional, (498)
"This place was lovely, they were always checking in to make sure we were ok and they had plenty of amenities for us to use!"
The price is S$150
includes taxes & fees
7 Jul - 8 Jul
Sleep Woodstock Motel
Echo Lake Inn
Exterior

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$269
includes taxes & fees
15 Jul - 16 Jul
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, (216)
"Very nice accommodations and convenient location."
The price is S$230
includes taxes & fees
13 Jul - 14 Jul
My Place Hotel-Randolph VT
Turn of River Lodge
Interior

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$177
includes taxes & fees
2 Aug - 3 Aug
Turn of River Lodge
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$511
includes taxes & fees
23 Jul - 24 Jul
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)
"Pleasant stay "
The price is S$194
includes taxes & fees
13 Jul - 14 Jul
Killington Mountain Lodge, Tapestry Collection by Hilton
Rent An Inn! Takeover The Birch Ridge W/ Your Group. Mountain Lodge: 11 Rooms, Bar, Fireplace. 28ppl 11 Bedroom Home
Interior

Rent An Inn! Takeover The Birch Ridge W/ Your Group. Mountain Lodge: 11 Rooms, Bar, Fireplace. 28ppl 11 Bedroom Home

2.0 star property
Rent An Inn! Takeover The Birch Ridge W/ Your Group. Mountain Lodge: 11 Rooms, Bar, Fireplace. 28ppl 11 Bedroom Home
Killington Grand Hotel
Exterior

Killington Grand Hotel

3.5 star property
8.8 out of 10, Excellent, (175)
"Place was awesome. Literally right by the bike park. Great room. Very clean."
Killington Grand Hotel
Snowed Inn
Front of property

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (353)
"Beautiful place to stay! 10/10 would recommend. You're going to love it!"
The price is S$238
includes taxes & fees
7 Jul - 8 Jul
Snowed Inn
Après Inn Killington
Exterior

Après Inn Killington

2.0 star property
9.4 out of 10, Exceptional, (130)
"Altogether a very welcoming place. Really enjoyed my 2-day stay there. "
The price is S$191
includes taxes & fees
13 Jul - 14 Jul
Après Inn Killington
Mountain Green
Indoor pool

Mountain Green

2.0 star property
6.6 out of 10, (10)
"The condo was very cozy for a family of four and suited us perfectly. Beds were comfortable and condo was clean. "
The price is S$321
includes taxes & fees
15 Jul - 16 Jul
Mountain Green
Summit Lodge
Fireplace

Summit Lodge

3.0 star property
8.6 out of 10, Excellent, (386)
"Love the old ski lodge feel and the layout of the hotel"
The price is S$245
includes taxes & fees
17 Jul - 18 Jul
Summit Lodge
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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Resorts in Pittsfield you'll enjoy

Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (521)
The price is S$699
includes taxes & fees
13 Jul - 14 Jul
Woodstock Inn & Resort

These family-friendly hotels in Pittsfield may fit your trip

Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (521)
The price is S$699
includes taxes & fees
13 Jul - 14 Jul
Woodstock Inn & 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.

Learn more about Pittsfield

Explore Pittsfield: its bars and more!

See all hotels in Pittsfield

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 Woodstock Inn & Resort 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?

Comfort Inn Rutland - Killington: Features continental, an indoor pool and free self parking. Woodstock Inn & Resort 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.