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

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Pittsfield holiday homes

Smart TV, offices

1. NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
North Sherburne
The price is £457
includes taxes & fees
19 Aug - 20 Aug
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
TV

2. 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 review)
"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 £461
includes taxes & fees
19 Aug - 20 Aug
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
Exterior

3. 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 £422
includes taxes & fees
19 Aug - 20 Aug
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Interior

4. 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 £480
includes taxes & fees
23 Aug - 24 Aug
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Coffee/tea maker, fridge, microwave, oven

5. Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails

Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails
North Sherburne
10.0 out of 10, Exceptional, (1 review)
"Great property to stay at highly recommend and will hopefully be staying again soon!"
United States
Robert R.
Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails
TV, offices

6. 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 £502
includes taxes & fees
19 Aug - 20 Aug
The Tower House | Hot Tub | Firepit | Dog-Friendly
House, 6 Bedrooms | Living area

7. Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is £545
includes taxes & fees
19 Aug - 20 Aug
Breakaway House by Killington Vacation Rentals
Interior

8. Private Killington Home w/ Indoor Hot Tub and 2 Living Rooms

Private Killington Home w/ Indoor Hot Tub and 2 Living Rooms
North Sherburne
The price is £563
includes taxes & fees
19 Aug - 20 Aug
Private Killington Home w/ Indoor Hot Tub and 2 Living Rooms
TV, fireplace, video games, table football

9. 25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
Killington
9.6 out of 10, Exceptional, (69 reviews)
"Great stay. Killer location!"
United States
Matthew P.
The price is £553
includes taxes & fees
19 Aug - 20 Aug
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
Private kitchen

10. 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 £174
includes taxes & fees
13 Sept - 14 Sept
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Interior

11. 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 £202
includes taxes & fees
19 Aug - 20 Aug
CozyDen - AC, Grill, Bike to Mountain, Porch!
TV, streaming services, music library, video library

12. 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 £415
includes taxes & fees
19 Aug - 20 Aug
Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
Smart TV, fireplace

13. 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, (3 reviews)
"great rental overall, the unit was well stocked, clean and have everything you need for your stay."
United States
matt d.
The price is £818
includes taxes & fees
19 Aug - 20 Aug
Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining
Interior

14. 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 £650
includes taxes & fees
24 Aug - 25 Aug
Snowarts- Game room, Fireplace, Close to golf!
Smart TV, fireplace, video games, stereo

15. 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, (20 reviews)
"Great location and excellent hosts "
United States
Peter G.
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
Smart TV, fireplace

16. 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.
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
House, 2 Bedrooms | Private kitchen | Coffee/tea maker, fridge, oven, toaster

17. Killington A-frame 2 Bedroom Home

Killington A-frame 2 Bedroom Home
3.0 star property
North Sherburne
Killington A-frame 2 Bedroom Home
Smart TV, fireplace, video games, stereo

18. 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 £388
includes taxes & fees
20 Aug - 21 Aug
HappyCub- AC, Hot Tub, Fire Pit, Game Room!
Terrace/patio

19. Estelle Cottage- Private Sauna, Hot tub, Pool, AC

Estelle Cottage- Private Sauna, Hot tub, Pool, AC
The Woods
10.0 out of 10, Exceptional, (1 review)
"Beautiful home and location. Great communication with host. I highly recommend this home, and will definitely book again."
United States
Edward M.
Estelle Cottage- Private Sauna, Hot tub, Pool, AC
Private kitchen

20. Hot Tub Getaway - Near Killington - Sleeps 12

Hot Tub Getaway - Near Killington - Sleeps 12
Killington
The price is £395
includes taxes & fees
2 Sept - 3 Sept
Hot Tub Getaway - Near Killington - Sleeps 12
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

The Shire Woodstock

The Shire Woodstock

8/10 Good
"We stayed in the River House and had two different rooms as we stayed one night each at the beginning and end of a longer trip to Canada. Both rooms were very clean. One room had a better view of the river than the other. There is construction occurring at the property and we weren’t made aware of it ahead of time so the sawing and drilling made sitting by the river and relaxing a little difficult. The whole property is getting a face lift. The outdoor space was lovely with chairs and fire pits. The location is great. Grocery store across the street and walkable to breakfast and shops. Would recommend but make sure you check about construction and confirm a good view of the river if that is important to you."
Jessica 1-night trip
Posted 8 hours ago
The Shire Woodstock

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
Accommodation
612 Holiday Homes
Lowest Price
£545
Highest Price
£545