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

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov
No exact matches found, but these alternatives could be just right

Recommended hotels in Pittsfield

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, (1,006 reviews)
"Great place to stay with the best staff!"
United States
Travis
The price is AU$222
includes taxes & fees
26 July - 27 July
The Mountain Inn at Killington
Exterior

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.6 out of 10, Exceptional, (246 reviews)
"Beautiful location, property provides everything to relax your mind and soul with genuinely kinds hosts, true gem!"
United States
MALGORZATA
The price is AU$322
includes taxes & fees
5 Aug - 6 Aug
Mountain Meadows Lodge
Outdoor wedding area

The Trailside Inn

The Trailside Inn
3.0 star property
North Sherburne
9.2 out of 10, Wonderful, (155 reviews)
"Great room - very clean and comfortable. Helpful and welcoming staff - even left out breakfast for our early departure."
United States
Niall
The price is AU$251
includes taxes & fees
27 July - 28 July
The Trailside Inn
Exterior

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (1,001 reviews)
"Great place to stay Very clean and close to a lot of stores breakfast was good clean room staff was great parking was free and great"
United States
Tarsha
The price is AU$249
includes taxes & fees
26 July - 27 July
Hampton Inn Rutland
Dinner served

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.2 out of 10, Very good, (1,008 reviews)
"Good breakfast"
United States
Darshil
The price is AU$193
includes taxes & fees
27 July - 28 July
Comfort Inn Rutland - Killington
The Jewel

The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
3.5 star property
Chittenden
9.0 out of 10, Wonderful, (121 reviews)
"Excellent stay "
United States
Kristen
The price is AU$507
includes taxes & fees
27 July - 28 July
The Mountain Top Inn & Resort
Exterior

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.8 out of 10, Excellent, (1,001 reviews)
"It was a very nice and comfortable stay Lee at the front desk was extremely"
United States
shaya
The price is AU$216
includes taxes & fees
28 July - 29 July
North Star Lodge and Resort
Exterior

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)
"Staff was very nice and went extra miles with finding activities I was interested in doing."
United States
Alex
The price is AU$282
includes taxes & fees
30 July - 31 July
Best Western Inn & Suites Rutland-Killington
Travel cot, free rollaway beds, free WiFi, individually decorated

Mountain Sports Inn

Mountain Sports Inn
2.0 star property
Killington
8.8 out of 10, Excellent, (1,000 reviews)
The price is AU$172
includes taxes & fees
30 July - 31 July
Mountain Sports Inn
32-inch flat-screen TV with cable channels, TV

Greenbrier Inn

Greenbrier Inn
2.0 star property
Killington
9.4 out of 10, Exceptional, (685 reviews)
"Nice, clean rooms with comfortable beds and plenty of room. The balconies are comfortable and private, sitting outside in the evening to unwind was nice. Breakfast was just right, plenty of choices and hot fresh coffee"
United States
David
The price is AU$278
includes taxes & fees
24 July - 25 July
Greenbrier 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, (1,001 reviews)
"We had a great stay. The staff was nice and the property was awesome. The beds were super comfy and the rooms were clean.Close to everything."
United States
Nicole
The price is AU$245
includes taxes & fees
2 Aug - 3 Aug
Killington Mountain Lodge, Tapestry Collection by Hilton
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, (495 reviews)
"I love that place"
United States
Tiffany
The price is AU$206
includes taxes & fees
16 Aug - 17 Aug
My Place Hotel-Randolph VT
Exterior

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area
2.5 star property
Rutland
6.8 out of 10, (1,005 reviews)
"The staff was incredibly kind and welcoming!! It’s an old place but the renovations they are working on make the rooms so comfortable. The bed was extraordinary!! The gentleman at the front was so kind and accommodating!!"
United States
katrina
The price is AU$172
includes taxes & fees
29 July - 30 July
Days Inn by Wyndham Rutland/Killington Area
Front of property

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (660 reviews)
"Wonderful hosts, nice historic inn in quaint town"
United States
Katherine
The price is AU$233
includes taxes & fees
11 Aug - 12 Aug
Brandon Inn
Front of property

Après Inn Killington

Après Inn Killington
2.0 star property
Killington
9.4 out of 10, Exceptional, (190 reviews)
"Location is great"
United States
Lei
The price is AU$230
includes taxes & fees
4 Aug - 5 Aug
Après Inn Killington
Front of property

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (400 reviews)
"Very convenient location with warmth and wonderful hosts."
United States
Martin
The price is AU$223
includes taxes & fees
29 July - 30 July
Snowed Inn
House, 2 Bedrooms | Property grounds

Killington A-frame 2 Bedroom Home

Killington A-frame 2 Bedroom Home
3.0 star property
North Sherburne
The price is AU$983
includes taxes & fees
31 July - 1 Aug
Killington A-frame 2 Bedroom Home
Exterior

Emrose Luxury Cabins

Emrose Luxury Cabins
2.0 star property
Brandon
9.0 out of 10, Wonderful, (104 reviews)
"Very nice, clean place to stay in Brandon. Visited family over the years and this was by far the best stay...."
United States
Tim
The price is AU$262
includes taxes & fees
26 July - 27 July
Emrose Luxury Cabins
Outdoor pool

Killington Grand Hotel

Killington Grand Hotel
3.5 star property
Base Area
9.0 out of 10, Wonderful, (216 reviews)
"Amazing place!"
United States
Sheryl
The price is AU$390
includes taxes & fees
26 July - 27 July
Killington Grand Hotel
Exterior

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,005 reviews)
"convenient location with very comfortable accommodations"
United States
Tonine
The price is AU$378
includes taxes & fees
20 Aug - 21 Aug
On The River Inn
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

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

8/10 Good
"Q"
Robert 1-night trip
Posted 2 hours ago
Comfort Inn Rutland - Killington

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
8,594
Accommodation
54 Cottages
Lowest Price
AU$122
Highest Price
AU$507

Frequently asked questions

What is there to do in Pittsfield near my cottage?
Whatever you're into, Pittsfield has loads to keep you busy. Pico Mountain at Killington Ski Resort, Gifford Woods State Park and Fire Tower are on many travellers' sightseeing itineraries. Don't go home without exploring Green Mountain National Golf Course, Lefferts Pond and Pico Pond either. With Expedia's hotel deals in Pittsfield, you'll be able to discover more fabulous attractions like these with the money you save.