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

Holiday Homes in Pittsfield

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Pittsfield holiday homes

Living area

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 NZ$1,059
includes taxes & fees
31 Aug - 1 Sept
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
Living area

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 NZ$1,076
includes taxes & fees
31 Aug - 1 Sept
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
Interior

3. 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 NZ$924
includes taxes & fees
31 Aug - 1 Sept
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Exterior

4. 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 NZ$924
includes taxes & fees
31 Aug - 1 Sept
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Room

5. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is NZ$457
includes taxes & fees
31 Aug - 1 Sept
Luxury Condo Tucked in the Heart of Killington
Living area

6. Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout

Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout
2.0 star property
Killington
The price is NZ$816
includes taxes & fees
2 Sept - 3 Sept
Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout
Living area

7. 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 NZ$1,116
includes taxes & fees
31 Aug - 1 Sept
The Tower House | Hot Tub | Firepit | Dog-Friendly
House, 6 Bedrooms | Living area

8. Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is NZ$1,229
includes taxes & fees
31 Aug - 1 Sept
Breakaway House by Killington Vacation Rentals
Living area

9. 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, (58 reviews)
"Perfect for a large group or a couple of families."
United States
Mark B.
The price is NZ$1,214
includes taxes & fees
2 Sept - 3 Sept
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
Property grounds

10. Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub

Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered 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 NZ$1,072
includes taxes & fees
31 Aug - 1 Sept
Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub
Living area

11. 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 NZ$943
includes taxes & fees
31 Aug - 1 Sept
Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
Interior

12. 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 NZ$457
includes taxes & fees
2 Sept - 3 Sept
CozyDen - AC, Grill, Bike to Mountain, Porch!
Living area

13. 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 NZ$1,101
includes taxes & fees
31 Aug - 1 Sept
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
Terrace/patio

14. 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 NZ$1,422
includes taxes & fees
1 Sept - 2 Sept
Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging
Private kitchen

15. 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 NZ$387
includes taxes & fees
7 Sept - 8 Sept
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Living area

16. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (16 reviews)
"The location was perfect, the property is very well maintained and comfortable. I would highly recommend this place!"
United States
Valerie
The price is NZ$291
includes taxes & fees
14 Sept - 15 Sept
Cozy Rutland Retreat
Living area

17. 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, (21 reviews)
"Great location and excellent hosts "
United States
Peter G.
The price is NZ$1,097
includes taxes & fees
1 Sept - 2 Sept
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
Exterior

18. 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, (70 reviews)
"Great stay. Killer location!"
United States
Matthew P.
The price is NZ$1,272
includes taxes & fees
3 Sept - 4 Sept
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
Living area

19. 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 NZ$1,868
includes taxes & fees
31 Aug - 1 Sept
Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining
Interior

20. SugarBear- Pool, AC, Sauna, Gym, Tennis!

SugarBear- Pool, AC, Sauna, Gym, Tennis!
The Woods
10.0 out of 10, Exceptional, (8 reviews)
"Great communication with the hosts, great welcome gifts! Housing was perfect, easy ride to Ramshead where youth lessons and childcare are, great pool for the kids after skiing. "
United States
Cécile B.
SugarBear- Pool, AC, Sauna, Gym, Tennis!
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 Meadows Lodge

Mountain Meadows Lodge

10/10 Excellent
"Great pleasant day recommend anybody"
Kenneth 1-night trip
Posted 4 hours ago
Mountain Meadows Lodge

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
205
Accommodation
604 Holiday Homes
Lowest Price
NZ$291
Highest Price
NZ$1,868