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

Search Vacation Homes in Pittsfield

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sep - 27 Sep
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Pittsfield vacation homes

Interior

Ski Home/Arcade Mountain Views Near Killington/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
United States
Kevin M.
The price is AED 391
AED 2,003 total
includes taxes & fees
29 Jul - 30 Jul
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Exterior

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
The price is AED 489
AED 2,129 total
includes taxes & fees
29 Jul - 30 Jul
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
TV, offices

The Tower House | Hot Tub | Firepit | Dog-Friendly

The Tower House | Hot Tub | Firepit | Dog-Friendly
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Great place, near everything and great customer service!!"
United States
Patrick B.
The price is AED 716
AED 2,478 total
includes taxes & fees
29 Jul - 30 Jul
The Tower House | Hot Tub | Firepit | Dog-Friendly
Private kitchen

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Mendon
9.8 out of 10, Exceptional, (6 reviews)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
United States
Aurore H.
The price is AED 327
AED 851 total
includes taxes & fees
29 Jul - 30 Jul
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
TV, fireplace, Netflix, foosball

Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.

Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
Killington
9.8 out of 10, Exceptional, (56 reviews)
"Perfect for a large group or a couple of families."
United States
Mark B.
The price is AED 675
AED 2,678 total
includes taxes & fees
29 Jul - 30 Jul
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
House, 6 Bedrooms | Living area

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is AED 725
AED 2,607 total
includes taxes & fees
29 Jul - 30 Jul
Breakaway House by Killington Vacation Rentals
Interior

CozyDen - AC, Grill, Bike to Mountain, Porch!

CozyDen - AC, Grill, Bike to Mountain, Porch!
Killington
9.4 out of 10, Exceptional, (3 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is AED 463
AED 1,000 total
includes taxes & fees
4 Aug - 5 Aug
CozyDen - AC, Grill, Bike to Mountain, Porch!
TV, streaming services, music library, video library

Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.

Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
Killington
7.0 out of 10, Good, (6 reviews)
"Excellent brief stay."
United States
Ron L.
The price is AED 465
AED 2,069 total
includes taxes & fees
29 Jul - 30 Jul
Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
Property grounds

Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.

Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.
Killington
10.0 out of 10, Exceptional, (1 review)
"Such an awesome place! The booking/check-in process was seamless and the location cannot be beat! Will definitely be booking again. "
United States
Catherine S.
The price is AED 709
AED 2,345 total
includes taxes & fees
29 Jul - 30 Jul
Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.
Terrace/patio

Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging

Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging
Killington
10.0 out of 10, Exceptional, (3 reviews)
"The accommodations exceeded the expectations in all ways.The booking, check in and communication with the hosts we're problem free and I would highly recommend this property and host to everyone seeking a beautiful and stress free get away."
United States
SHEEPDOG 1.
The price is AED 1,053
AED 2,944 total
includes taxes & fees
30 Jul - 31 Jul
Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging
Coffee/tea maker, fridge, microwave, oven

Summit House on George | Renovated | 5 Mins to K-1 | Lift & Rental Deals

Summit House on George | Renovated | 5 Mins to K-1 | Lift & Rental Deals
Killington
10.0 out of 10, Exceptional, (1 review)
"Absolutely loved this house. Our stay was perfect. It was so close to the mountain and all the restaurants. It was not on a busy street, so private and clean and overall amazing place to stay. We would definitely choose to stay again here!!"
United States
Sandra G.
Summit House on George | Renovated | 5 Mins to K-1 | Lift & Rental Deals
Smart TV, fireplace

Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining

Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining
Killington
10.0 out of 10, Exceptional, (2 reviews)
"House and hot tub were all well maintained. Loved the decor!"
United States
Melinda T.
Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining
Interior

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Killington
The price is AED 762
AED 1,941 total
includes taxes & fees
29 Jul - 30 Jul
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Smart TV, fireplace, video games, stereo

HappyCub- AC, Hot Tub, Fire Pit, Game Room!

HappyCub- AC, Hot Tub, Fire Pit, Game Room!
Killington
10.0 out of 10, Exceptional, (27 reviews)
"Great communication, location, and all around stay!"
United States
Ashley K.
The price is AED 810
AED 1,974 total
includes taxes & fees
29 Jul - 30 Jul
HappyCub- AC, Hot Tub, Fire Pit, Game Room!
Smart TV, fireplace, video games, stereo

The Big Lebearski- AC, Grill, Fire Pit, Hot tub!

The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
Killington
10.0 out of 10, Exceptional, (19 reviews)
"Great location and excellent hosts "
United States
Peter G.
The price is AED 929
AED 2,432 total
includes taxes & fees
4 Aug - 5 Aug
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
House, 2 Bedrooms | Private kitchen | Coffee/tea maker, fridge, oven, toaster

Killington A-frame 2 Bedroom Home

Killington A-frame 2 Bedroom Home
3.0 star property
North Sherburne
The price is AED 1,286
AED 2,449 total
includes taxes & fees
31 Jul - 1 Aug
Killington A-frame 2 Bedroom Home
Interior

Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.4 out of 10, Exceptional, (45 reviews)
"Nice location off of Route 100 there was a little road noise but the house is situated a bit back. The seating was super comfy and the kitchen was nicely stocked for cooking. It was awesome to be able to bring our pup! "
United States
Melissa P.
Beautiful home located in the Mad River Valley
Interior

Snowarts- Game room, Fireplace, Close to golf!

Snowarts- Game room, Fireplace, Close to golf!
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Great place for a large group. It was pet friendly and that is a plus for us. Very clean and reasonably priced."
United States
Tammy W.
The price is AED 1,579
AED 3,185 total
includes taxes & fees
29 Jul - 30 Jul
Snowarts- Game room, Fireplace, Close to golf!
TV, fireplace

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Bridgewater
8.8 out of 10, Excellent, (3 reviews)
"Great place for a ski weekend"
United States
Kathryn F.
The price is AED 805
AED 2,566 total
includes taxes & fees
29 Jul - 30 Jul
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Smart TV, fireplace

Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna

Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
The Woods
10.0 out of 10, Exceptional, (7 reviews)
"Great location and a great place. Felt right at home"
United States
Tyler B.
The price is AED 1,182
AED 2,442 total
includes taxes & fees
30 Jul - 31 Jul
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

On The River Inn

On The River Inn

10/10 Excellent
"Very well-maintained property and nice guest rooms and dining room/bar is beautiful. The country breakfast was also a plus. Would definitely come back here!"
Susan 1-night trip
Posted 14 hours ago
On The River Inn