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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr
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Recommended hotels in Pittsfield

Outdoor dining
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

North Sherburne
10.0 out of 10, Exceptional, (1)
"Peak Hill, is a lovely and very clean home, with a fully stocked kitchen and comfy beds. This home is exactly as the pictures that are shown. We had a very small issue with the door lock (battery), called and it was fixed right away, wonderful service. The owner, Geri, we had the opportunity to meet and she is very kind and a pleasure to speak with. We travel alot and l bring pretty much my own kitchen, pillow...... with me where ever l go. However, l would of been fine using all at this...
United States
Essa R.
The price is AED 695
AED 2,298 total
includes taxes & fees
15 Dec - 16 Dec
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
House, 4 Bedrooms | Exterior
The Getaway 4 Bedroom Home

The Getaway 4 Bedroom Home

3.0 star property
Pittsfield
The price is AED 1,559
AED 3,552 total
includes taxes & fees
11 Dec - 12 Dec
The Getaway 4 Bedroom Home
Exterior
The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!

The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!

Pittsfield
The price is AED 1,212
AED 2,991 total
includes taxes & fees
11 Dec - 12 Dec
The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!
Exterior
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 star property
Rutland
8.0 out of 10, Very Good, (1004)
"Clean, great steak house by the hotel"
United States
Caridad
The price is AED 465
AED 512 total
includes taxes & fees
11 Dec - 12 Dec
Comfort Inn Rutland - Killington
Terrace/patio
On The River Inn

On The River Inn

4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1000)
"This place was charming!! Enjoyed everything about it and so much to do right there in the inn."
United States
Ross
The price is AED 709
AED 914 total
includes taxes & fees
22 Dec - 23 Dec
On The River Inn
Deluxe Suite | Exterior
Sleep Woodstock Motel

Sleep Woodstock Motel

2.0 star property
Woodstock
9.6 out of 10, Exceptional, (548)
"The staff at this motel are 5 star! Lisa went above and beyond to make my stay easy since I was there for a medical procedure. "
United States
Crystal
The price is AED 284
AED 603 total
includes taxes & fees
11 Dec - 12 Dec
Sleep Woodstock Motel
Terrace/patio
Mountain Meadows Lodge

Mountain Meadows Lodge

3.5 star property
Killington
9.4 out of 10, Exceptional, (178)
"All round fantastic place to stay "
United Kingdom
Stephen
The price is AED 626
AED 781 total
includes taxes & fees
11 Dec - 12 Dec
Mountain Meadows Lodge
Front of property
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (342)
"Awesome staff and great room with Kitchenette"
United States
Mary
The price is AED 366
AED 399 total
includes taxes & fees
4 Jan - 5 January 2026
My Place Hotel-Randolph VT
Front of property - evening/night
Mountain Valley Retreat

Mountain Valley Retreat

2.5 star property
Killington
9.6 out of 10, Exceptional, (189)
"Absolutely lovely stay!"
United States
Elizabeth
The price is AED 441
AED 498 total
includes taxes & fees
11 Dec - 12 Dec
Mountain Valley Retreat
Exterior
Hampton Inn Rutland

Hampton Inn Rutland

2.5 star property
Rutland
9.0 out of 10, Wonderful, (968)
"Very clean, good location, and super helpful staff!"
United States
Sheryl
The price is AED 541
AED 595 total
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn Rutland
Breakfast and dinner served
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 star property
Killington
9.2 out of 10, Wonderful, (956)
"Great place to stay!"
United States
Stephen
The price is AED 716
AED 827 total
includes taxes & fees
14 Dec - 15 Dec
The Mountain Inn at Killington
Front of property
Mountain Sports Inn

Mountain Sports Inn

2.0 star property
The Woods
8.8 out of 10, Excellent, (980)
"Everything was superb . Staff is very friendly and breakfast is fabulous ."
United States
Bradford
The price is AED 400
AED 440 total
includes taxes & fees
11 Dec - 12 Dec
Mountain Sports Inn
Garden
North Star Lodge and Resort

North Star Lodge and Resort

2.0 star property
Killington
8.6 out of 10, Excellent, (1000)
"Spotless room also very accommodating and friendly! Loved our short stay!"
United States
Candace
North Star Lodge and Resort
Exterior
Courtyard Middlebury

Courtyard Middlebury

3.0 star property
Middlebury
8.8 out of 10, Excellent, (543)
"Great hotel, fairly centered , great staff!"
United States
Angelo
The price is AED 426
AED 469 total
includes taxes & fees
4 Jan - 5 January 2026
Courtyard Middlebury
Front of property
Turn of River Lodge

Turn of River Lodge

2.5 star property
Killington
8.8 out of 10, Excellent, (270)
"We enjoyed our stay. Close proximity to a lot of things to see and do. "
United States
Linda
The price is AED 465
AED 511 total
includes taxes & fees
11 Dec - 12 Dec
Turn of River Lodge
Exterior
Brandon Inn

Brandon Inn

3.0 star property
Brandon
8.8 out of 10, Excellent, (564)
"Enjoyed our stay at the Brandon Inn very much!"
United States
Lesley
The price is AED 404
AED 445 total
includes taxes & fees
11 Dec - 12 Dec
Brandon Inn
Exterior
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, (1002)
"Staff was very helpful and room service was great."
United States
Ankita
The price is AED 599
AED 659 total
includes taxes & fees
14 Dec - 15 Dec
Killington Mountain Lodge, Tapestry Collection by Hilton
Exterior
Middlebury Sweets Motel

Middlebury Sweets Motel

2.5 star property
Middlebury
8.6 out of 10, Excellent, (388)
"Friendly staff, clean, comfortable and convenient to downtown. "
United States
Melissa
The price is AED 400
AED 440 total
includes taxes & fees
11 Dec - 12 Dec
Middlebury Sweets Motel
Front of property
The Jackson

The Jackson

4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (256)
"Very cute inn, the restaurant was a plus. Had a great dinner there and def will come back. "
United States
Jaunita
The Jackson
Front of property
The Shire Woodstock

The Shire Woodstock

3.0 star property
Woodstock
8.8 out of 10, Excellent, (889)
"Wonderful place to stay!"
United States
Robin
The Shire Woodstock
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

Mountain Sports Inn

Mountain Sports Inn

10/10 Excellent
"Everything was superb . Staff is very friendly and breakfast is fabulous ."
Bradford 2-night trip
Posted 2 days ago
Mountain Sports Inn