A lake surrounded by autumn-colored trees and a rocky shoreline.

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28
No exact matches found, but these alternatives could be just right

Recommended hotels in Pittsfield

A stone fireplace with a sign above it reading "Trailside Lodge."

1. The Trailside Inn

The Trailside Inn
3.0 star property
North Sherburne
9.2 out of 10, Wonderful, (167 reviews)
"Such a welcoming and friendly place for a stay"
United States
Marc
The price is CA $223
CA $245 total
includes taxes & fees
Nov 29 - Nov 30
The Trailside Inn
A covered outdoor deck with wicker furniture, a table, and a built-in grill.

2. Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.6 out of 10, Exceptional, (370 reviews)
"This place is awesome, Clean, beautiful, great location, great staff, super breakfast."
United States
Kathy
The price is CA $192
CA $246 total
includes taxes & fees
Nov 9 - Nov 10
Mountain Meadows Lodge
A dining area with a wooden table and chairs, a fireplace, and a cozy seating area with a couch and a TV.

3. Mountain Sports Inn

Mountain Sports Inn
2.0 star property
Killington
8.8 out of 10, Excellent, (1,004 reviews)
"Would definitely stay again"
United States
Pamela
The price is CA $152
CA $168 total
includes taxes & fees
Nov 22 - Nov 23
Mountain Sports Inn
A spacious living room with a high ceiling, wooden beams, a staircase, and a large window.

4. Greenbrier Inn

Greenbrier Inn
2.0 star property
Killington
9.4 out of 10, Exceptional, (706 reviews)
"Very friendly staff with easy check in and out. Breakfast was fast and convenient and great location!"
United States
Jeff
The price is CA $244
CA $282 total
includes taxes & fees
Nov 15 - Nov 16
Greenbrier Inn
A spacious living room with a fireplace, leather sofas, a wooden coffee table, and a view of the outdoors.

5. North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.6 out of 10, Excellent, (1,001 reviews)
"Perfect service and friendly staff!!"
United States
Toghrul
The price is CA $165
CA $182 total
includes taxes & fees
Nov 12 - Nov 13
North Star Lodge and Resort
A large, red, L-shaped building with multiple windows and a snow-covered roof, surrounded by a snowy landscape and mountains in the background.

6. Killington Haus

Killington Haus
2.0 star property
Killington
9.2 out of 10, Wonderful, (71 reviews)
"Clean room, clean place, warm and cozy inside. A great place to stay in Killington!"
United States
Ivan
The price is CA $169
CA $186 total
includes taxes & fees
Nov 8 - Nov 9
Killington Haus
A spacious room with large windows, a stone wall, and a wooden ceiling.

7. The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
3.5 star property
Chittenden
9.0 out of 10, Wonderful, (132 reviews)
"Oh wow!! I would stay here again tomorrow! Beautiful property, restaurant has amazing food and convenient location. We stayed in the Long View Barn, the 60 mile view was even more spectacular than we imagined!"
United States
Allison
The price is CA $412
CA $518 total
includes taxes & fees
Nov 8 - Nov 9
The Mountain Top Inn & Resort
A building with a modern design, featuring large windows and a covered outdoor seating area.

8. The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (1,004 reviews)
"Great hotel!"
United States
Petra
The price is CA $187
CA $216 total
includes taxes & fees
Nov 8 - Nov 9
The Mountain Inn at Killington
A large, stone and wood lodge with a sign reading 'The Snowed Inn,' surrounded by snow-covered trees and a snow-covered driveway.

9. Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (436 reviews)
"It was a fantastic stay and all that we wanted in a charming inn on the mountain."
United States
Marleen
The price is CA $193
CA $233 total
includes taxes & fees
Dec 6 - Dec 7
Snowed Inn
A sign for 'Apres Inn' in KILLINGTON, VT, with a modern building featuring large windows and a balcony.

10. Après Inn Killington

Après Inn Killington
2.0 star property
Killington
9.4 out of 10, Exceptional, (208 reviews)
"modern and clean, wifi worked great"
United States
Kylie
The price is CA $193
CA $212 total
includes taxes & fees
Nov 11 - Nov 12
Après Inn Killington
A rustic cabin with a wooden deck, surrounded by dense greenery and a rocky landscape.

11. Gnome Home Mountain Ski Chalet w/Sauna Killington

Gnome Home Mountain Ski Chalet w/Sauna Killington
Stockbridge
10.0 out of 10, Exceptional, (7 reviews)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
The price is CA $268
CA $619 total
includes taxes & fees
Nov 16 - Nov 17
Gnome Home Mountain Ski Chalet w/Sauna Killington
A two-story building with a dark brown exterior, a covered porch, and a number '303' sign.

12. Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings

Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings
North Sherburne
8.0 out of 10, Very good, (17 reviews)
"We had a great time!"
United States
Matthew R.
The price is CA $139
CA $510 total
includes taxes & fees
Nov 7 - Nov 8
Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings
A large, multi-story hotel with a prominent entrance and a staircase leading to the upper levels.

13. Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 star property
Killington
7.4 out of 10, Good, (1,001 reviews)
"Great hotel with an amazing staff."
United States
Richard
The price is CA $201
CA $221 total
includes taxes & fees
Nov 12 - Nov 13
Killington Mountain Lodge, Tapestry Collection by Hilton
A spacious indoor area with a large dining table, several chairs, and a sofa. There is a glass door leading outside, and the room has a wooden ceiling structure.

14. Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
2.5 star property
Rutland
8.8 out of 10, Excellent, (1,000 reviews)
"clean, staff welcoming, and breakfast was solid."
United States
Bryce
The price is CA $225
CA $248 total
includes taxes & fees
Nov 12 - Nov 13
Best Western Inn & Suites Rutland-Killington
An aerial view of a residential area with houses, a swimming pool, and a parking lot.

15. Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
Killington
9.4 out of 10, Exceptional, (10 reviews)
"Beautiful place . My sister was visiting USA/ Vermont for the first time . We went to the Breakfast cafe next door it was amazing . "
United States
Asad B.
The price is CA $135
CA $370 total
includes taxes & fees
Nov 8 - Nov 9
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
A living room with a sofa, a dining table with chairs, a kitchen area with wooden cabinets, and a bar.

16. Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
Killington
9.8 out of 10, Exceptional, (14 reviews)
"We had such a great time staying here. It was clean, cozy and so convenient to walk right out the door to the slopes! "
United States
Susanne B.
The price is CA $168
CA $445 total
includes taxes & fees
Nov 8 - Nov 9
Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
A hotel lobby with a reception desk, seating area, and a coffee table with a fruit basket.

17. Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.0 out of 10, Very good, (1,001 reviews)
"This was a good hotel for a decent price."
United States
Leila
The price is CA $175
CA $192 total
includes taxes & fees
Nov 12 - Nov 13
Comfort Inn Rutland - Killington
Front of property

18. Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (733 reviews)
"Very unique and well maintained/restored historic property. It's a cool place."
United States
Amy
The price is CA $156
CA $172 total
includes taxes & fees
Nov 17 - Nov 18
Brandon Inn
A spacious living room with a fireplace, a television, and a large window.

19. 4BR Killington Home Perfect for Families, Pet-Friendly

4BR Killington Home Perfect for Families, Pet-Friendly
North Sherburne
10.0 out of 10, Exceptional, (24 reviews)
"Our group had a wonderful ski weekend at the house! It was well stocked with everything we needed and the fireplace was perfect to relax near after a day on the slopes. "
United States
Christina V.
The price is CA $342
CA $944 total
includes taxes & fees
Nov 8 - Nov 9
4BR Killington Home Perfect for Families, Pet-Friendly
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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Top Pittsfield Hotel Reviews

On The River Inn

On The River Inn

10/10 Excellent
"We loved our spacious room, the sauna, pool/hot tub and game room! We were welcomed with a s’mores pack and spent the evening by the cozy fire pit. Lovely hotel!"
Rachel 1-night trip
Posted 2 hours ago
On The River Inn

Find out more about Pittsfield

Pittsfield Condo Resorts information

Number of reviews
1,567
Accommodation
0 Condo Resorts
Lowest Price
CA $168
Highest Price
CA $944

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