Pittsfield Hotels from S$132

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10 Jul - 11 Jul
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11 Jul - 12 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
Enjoy the serene forest views from the cabin's expansive windows and cozy porch.

Serene Architect-designed Vermont Chalet 4 Bedroom Home

3.5 star property
The price is S$1,068
includes taxes & fees
11 Jul - 12 Jul
Serene Architect-designed Vermont Chalet 4 Bedroom Home
Stay At Jimmy's
Relax in a serene space with a large mirror, plush seating area, and a touch of greenery.

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (35)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
The price is S$351
includes taxes & fees
14 Jul - 15 Jul
Stay At Jimmy's
The Shire Woodstock
Surrounded by lush forests and a meandering river, this picturesque village offers a serene escape.

The Shire Woodstock

3.0 star property
8.8 out of 10, Excellent, (776)
"Great location!! Very accommodating and clean."
The Shire Woodstock
The Vesper
Relax in this serene bedroom with a large bed, two windows, and a cozy reading nook.

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$211
includes taxes & fees
15 Jul - 16 Jul
The Vesper
Woodstock Inn & Resort
Stately room with a checkered floor, classic bench, and fireplace view.

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (521)
"Relaxing "
The price is S$702
includes taxes & fees
10 Aug - 11 Aug
Woodstock Inn & Resort
The Jackson
Cozy space with a fireplace, sofa, and coffee table, perfect for unwinding.

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
Enjoy cooking in this well-equipped kitchen with a dishwasher, microwave, stove, and refrigerator, plus a convenient island with sink and countertop workspace.

On The River Inn

4.0 star property
9.4 out of 10, Exceptional, (1000)
"Wonderful place to stay. "
The price is S$313
includes taxes & fees
13 Jul - 14 Jul
On The River Inn
Lincoln Inn & Gallery
Interior

Lincoln Inn & Gallery

3.0 star property
9.6 out of 10, Exceptional, (16)
"Beautiful Inn and grounds."
The price is S$167
includes taxes & fees
15 Jul - 16 Jul
Lincoln Inn & Gallery
Sleep Woodstock Motel
Cozy living area with a fireplace, comfortable seating, and a staircase leading to an upper level.

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
21 Jul - 22 Jul
Sleep Woodstock Motel
Echo Lake Inn
Classic hotel with a central entrance and symmetrical facade.

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$267
includes taxes & fees
14 Jul - 15 Jul
Echo Lake Inn
My Place Hotel-Randolph VT
Fully equipped kitchen with a refrigerator, sink, microwave, and coffee maker.

My Place Hotel-Randolph VT

2.0 star property
9.4 out of 10, Exceptional, (217)
"Very nice accommodations and convenient location."
The price is S$226
includes taxes & fees
23 Jul - 24 Jul
My Place Hotel-Randolph VT
Turn of River Lodge
Cyclists stand in line on the driveway, surrounded by lush greenery and a charming rural setting.

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."
Turn of River Lodge
Fall Line Condos by Killington VR - 1 Bedrooms
Cozy living room with a brick fireplace, flat-screen TV, and comfortable sofa.

Fall Line Condos by Killington VR - 1 Bedrooms

3.5 star property
The price is S$513
includes taxes & fees
23 Jul - 24 Jul
Fall Line Condos by Killington VR - 1 Bedrooms
Killington Mountain Lodge, Tapestry Collection by Hilton
Experience the unique architecture and tranquil courtyard with a swimming pool and waterfall, surrounded by seating areas and balconies.

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 star property
7.2 out of 10, Good, (1003)
"Pleasant stay "
The price is S$202
includes taxes & fees
21 Jul - 22 Jul
Killington Mountain Lodge, Tapestry Collection by Hilton
Killington Grand Hotel
Sit by the fire pit in a serene outdoor space surrounded by snow-covered benches.

Killington Grand Hotel

3.5 star property
8.8 out of 10, Excellent, (177)
"Place was awesome. Literally right by the bike park. Great room. Very clean."
Killington Grand Hotel
Snowed Inn
Step into the warm and inviting entrance of this charming lodge, featuring a stone facade and wooden beams.

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (354)
"Beautiful place to stay! 10/10 would recommend. You're going to love it!"
The price is S$239
includes taxes & fees
13 Jul - 14 Jul
Snowed Inn
Après Inn Killington
Experience the serene surroundings of Apres Inn, where a contemporary building meets nature's beauty.

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$192
includes taxes & fees
13 Jul - 14 Jul
Après Inn Killington
Mountain Green
Relax by the rectangular pool surrounded by a paved deck and shaded seating area.

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$324
includes taxes & fees
15 Jul - 16 Jul
Mountain Green
Summit Lodge
Cozy living room with a stone fireplace, comfortable sofa, and wooden coffee table.

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$246
includes taxes & fees
17 Jul - 18 Jul
Summit Lodge
North Star Lodge and Resort
Two single beds with made bedspreads and pillows, a large window with blinds, and wall-mounted paintings create a clean and inviting space.

North Star Lodge and Resort

2.0 star property
8.6 out of 10, Excellent, (1000)
"Good value hotel in an excellent location."
North Star Lodge and 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.
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Family-friendly hotels in Pittsfield you'll enjoy

Woodstock Inn & Resort
Stately room with a checkered floor, classic bench, and fireplace view.

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (521)
The price is S$702
includes taxes & fees
10 Aug - 11 Aug
Woodstock Inn & Resort

Hotels with a hot tub in Pittsfield may fit your trip

Stay At Jimmy's
Relax in a serene space with a large mirror, plush seating area, and a touch of greenery.

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (35)
The price is S$351
includes taxes & fees
14 Jul - 15 Jul
Stay At Jimmy's

Check out pet-friendly hotels in Pittsfield

Serene Architect-designed Vermont Chalet 4 Bedroom Home
Enjoy the serene forest views from the cabin's expansive windows and cozy porch.

Serene Architect-designed Vermont Chalet 4 Bedroom Home

3.5 star property
The price is S$1,068
includes taxes & fees
11 Jul - 12 Jul
Serene Architect-designed Vermont Chalet 4 Bedroom Home
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 North Star Lodge and Resort. 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.