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

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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

A spacious living area with a red sectional sofa, a wooden dining table, and a kitchen in the background.

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, 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 HK$1,524
HK$5,010 total
includes taxes & fees
26 Aug - 27 Aug
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
A modern living room with a red sectional sofa, a round coffee table, wooden ceiling beams, a kitchen area, and a balcony with a view of trees.

2. 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 HK$1,468
HK$4,937 total
includes taxes & fees
26 Aug - 27 Aug
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

3. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is HK$622
HK$2,146 total
includes taxes & fees
26 Aug - 27 Aug
Luxury Condo Tucked in the Heart of Killington

4. New Luxury Cabin-Sauna, Hot Tub, Arcade, King Beds

New Luxury Cabin-Sauna, Hot Tub, Arcade, King Beds
Killington
The price is HK$3,262
HK$6,810 total
includes taxes & fees
31 Aug - 1 Sept
New Luxury Cabin-Sauna, Hot Tub, Arcade, King Beds

5. 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 HK$1,043
HK$4,603 total
includes taxes & fees
26 Aug - 27 Aug
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
A living room with a wooden console table, a potted plant, and two clocks. A staircase and a fireplace with a TV are in the background.

6. 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 HK$1,043
HK$4,605 total
includes taxes & fees
26 Aug - 27 Aug
Ski Home/Arcade Mountain Views Near Killington/Woodstock
A cozy living room with a stone fireplace, a large sectional sofa, and a wooden ceiling.

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 Tower House | Hot Tub | Firepit | Dog-Friendly
A cozy living room with a sectional sofa, a coffee table, and a fireplace.

8. Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is HK$1,665
HK$5,697 total
includes taxes & fees
26 Aug - 27 Aug
Breakaway House by Killington Vacation Rentals
A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

9. 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 HK$727
HK$1,849 total
includes taxes & fees
26 Aug - 27 Aug
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

10. 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 HK$643
HK$1,384 total
includes taxes & fees
14 Sept - 15 Sept
Cozy Rutland Retreat
A cozy living room with a fireplace, a television, and a view of a snowy deck.

11. 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 HK$1,440
HK$5,716 total
includes taxes & fees
27 Aug - 28 Aug
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.

12. 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 HK$1,347
HK$5,998 total
includes taxes & fees
26 Aug - 27 Aug
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
A modern living room with a flat-screen TV, grey sofas, a dining table with chairs, and a large window with a view of greenery.

13. 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 HK$1,132
HK$2,324 total
includes taxes & fees
30 Aug - 31 Aug
CozyDen - AC, Grill, Bike to Mountain, Porch!
A spacious living area with a fireplace, a television, and a dining area with natural light.

14. 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 HK$992
HK$4,417 total
includes taxes & fees
26 Aug - 27 Aug
Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
A cabin with a wooden deck, surrounded by lush greenery and a garden with purple flowers.

15. 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.
Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.
A modern house with a stone facade, a large deck, and outdoor seating.

16. 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.
Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging
A cozy living room with a brick fireplace, a sofa, a coffee table, and a television mounted on a wooden cabinet.

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, (20 reviews)
"Great location and excellent hosts "
United States
Peter G.
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
A spacious living room with a stone fireplace, large windows, and a cozy seating area.

18. 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.
Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining
A cozy living room with a stone fireplace, a sofa set, and a dining table.

19. 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 HK$2,524
HK$5,212 total
includes taxes & fees
26 Aug - 27 Aug
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
A spacious kitchen with a central island, wooden ceiling, and large windows.

20. Hot Tub Getaway - Near Killington - Sleeps 12

Hot Tub Getaway - Near Killington - Sleeps 12
Killington
The price is HK$2,313
HK$4,509 total
includes taxes & fees
23 Sept - 24 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
"It was a nice and cozy place to stay and experience Woodstock VT."
Clayton 2-night trip
Posted 3 hours ago
The Shire Woodstock

Find out more about Pittsfield

Pittsfield Vacation Homes information

Number of reviews
196
Accommodation
604 Vacation Homes
Lowest Price
HK$1,384
Highest Price
HK$6,810

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