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Our top choices for Pittsfield holiday homes

1. 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, VermontNorth Sherburne
10.0 out of 10, Exceptional, (1 review)
The price is AU$877
includes taxes & fees
15 Nov - 16 Nov

2. NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat ParkingNorth Sherburne
10.0 out of 10, Exceptional, (2 reviews)
The price is AU$952
includes taxes & fees
15 Nov - 16 Nov

3. Ski Home/Arcade Mountain Views Near Killington/Woodstock
Ski Home/Arcade Mountain Views Near Killington/WoodstockStockbridge
10.0 out of 10, Exceptional, (3 reviews)
The price is AU$815
includes taxes & fees
15 Nov - 16 Nov

4. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/WoodstockStockbridge
10.0 out of 10, Exceptional, (3 reviews)
The price is AU$815
includes taxes & fees
15 Nov - 16 Nov

5. Luxury Condo Tucked in the Heart of Killington
Luxury Condo Tucked in the Heart of KillingtonKillington
10.0 out of 10, Exceptional, (1 review)
The price is AU$335
includes taxes & fees
15 Nov - 16 Nov

6. Liquid Lodge Lower: 2BR Duplex near Killington with 1 PM Checkout
Liquid Lodge Lower: 2BR Duplex near Killington with 1 PM CheckoutKillington
The price is AU$670
includes taxes & fees
15 Nov - 16 Nov

7. Barrows Ridge Chalet | Mountain Views, Private Hot Tub, 4 Bedrooms
Barrows Ridge Chalet | Mountain Views, Private Hot Tub, 4 BedroomsKillington
The price is AU$1,196
includes taxes & fees
15 Nov - 16 Nov

8. Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington
Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to KillingtonKillington
9.0 out of 10, Wonderful, (7 reviews)
The price is AU$705
includes taxes & fees
15 Nov - 16 Nov

9. 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 ChargingKillington
9.0 out of 10, Wonderful, (6 reviews)
The price is AU$1,244
includes taxes & fees
15 Nov - 16 Nov

10. The Tower House | Hot Tub | Firepit | Dog-Friendly
The Tower House | Hot Tub | Firepit | Dog-FriendlyKillington
6.8 out of 10, (3 reviews)
The price is AU$1,150
includes taxes & fees
15 Nov - 16 Nov

11. The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi
The Woods Resort Killington - 2B Townhouse with Spa, Pool & JacuzziThe Woods
The price is AU$529
includes taxes & fees
15 Nov - 16 Nov

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)

13. 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, (59 reviews)
The price is AU$1,208
includes taxes & fees
15 Nov - 16 Nov

14. Private Killington Home w/ Indoor Hot Tub and 2 Living Rooms
Private Killington Home w/ Indoor Hot Tub and 2 Living RoomsNorth Sherburne
10.0 out of 10, Exceptional, (1 review)
The price is AU$1,338
includes taxes & fees
15 Nov - 16 Nov

15. Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining
Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & DiningKillington
10.0 out of 10, Exceptional, (3 reviews)
The price is AU$1,659
includes taxes & fees
15 Nov - 16 Nov

16. 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 DealsKillington
10.0 out of 10, Exceptional, (1 review)
The price is AU$845
includes taxes & fees
15 Nov - 16 Nov

17. Classic Killington Ski Chalet for 8 w/ Gear Room, 2 Fireplaces, 5 Mins to Slopes
Classic Killington Ski Chalet for 8 w/ Gear Room, 2 Fireplaces, 5 Mins to SlopesKillington
The price is AU$1,377
includes taxes & fees
15 Nov - 16 Nov

18. Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ FireplaceKillington
9.0 out of 10, Wonderful, (2 reviews)
The price is AU$793
includes taxes & fees
15 Nov - 16 Nov

19. 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, (73 reviews)
The price is AU$1,242
includes taxes & fees
16 Nov - 17 Nov

20. SnowArts, Wood Burning fireplace, Close to slopes
SnowArts, Wood Burning fireplace, Close to slopesKillington
9.0 out of 10, Wonderful, (2 reviews)
The price is AU$1,198
includes taxes & fees
13 Nov - 14 Nov
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.
Learn more about Pittsfield
Nestled in Vermont's Green Mountains, Pittsfield offers excellent hiking on the Long Trail and thrilling mountain biking at Green Mountain Trails. Riverside picnics along the Tweed River provide peaceful breaks between seasonal activities at nearby Killington Resort.





























































































