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

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Pittsfield vacation homes

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.

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
10.0 out of 10, Exceptional, (2 reviews)
"On our 30th Anniversary trip to Vermont, New Hampshire and Maine we fell in love with Killington, Vermont. So much so we left the coast of Maine and last minute booked our remaining two nights back in Killington at the Poweder Run Lodge. The lodge was a wonderful experience! The location was beautiful, spacious, clean, had a fully stocked kitchen and spectacular views. The hosts were kind and easy to communicate with. We are older and need a continuous running fan and a little softer bed when we...
United States
Heidi P.
The price is ￥36,057
￥107,991 total
includes taxes & fees
Oct 28 - Oct 29
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
A spacious living area with a red sectional sofa, a wooden dining table, and a kitchen in the background.

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.
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
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.

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 ￥20,960
￥91,267 total
includes taxes & fees
Oct 28 - Oct 29
Ski Home/Arcade Mountain Views Near Killington/Woodstock
A snow-covered forest with a cabin.

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 ￥20,878
￥90,908 total
includes taxes & fees
Oct 28 - Oct 29
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
A spacious living room with a fireplace, a television, and a large window.

5. 4BR Killington Home Perfect for Families, Pet-Friendly

4BR Killington Home Perfect for Families, Pet-Friendly
North Sherburne
10.0 out of 10, Exceptional, (24 reviews)
"Our group had a wonderful ski weekend at the house! It was well stocked with everything we needed and the fireplace was perfect to relax near after a day on the slopes. "
United States
Christina V.
The price is ￥38,374
￥116,809 total
includes taxes & fees
Oct 28 - Oct 29
4BR Killington Home Perfect for Families, Pet-Friendly
A kitchen with a central island, two bar stools, pendant lights, and a view of the living area through an open archway.

6. 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.
The price is ￥32,786
￥116,385 total
includes taxes & fees
Nov 11 - Nov 12
Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails
A kitchen with white cabinetry, a stainless steel refrigerator, a coffee maker, and a dining area with two chairs.

7. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
10.0 out of 10, Exceptional, (1 review)
"We were very surprised. The accommodation's well worth the amount we paid. I was surprised how from the start to the close of our Anniversary get away It was such an easygoing experience. The host left fresh towels and bedding linens. The host kept in contact the entire way booking this condo. It was roomy nice Quiet!! I loved the privacy yet close to everything Killington has to offer. Our anniversary was special as we went with the host recommendation for a local resturaunt the Garlic. We have...
United States
Melinda D.
The price is ￥12,678
￥43,316 total
includes taxes & fees
Nov 3 - Nov 4
Luxury Condo Tucked in the Heart of Killington
A wooden interior with a bench and shelves, a door with a handle, and a tiled floor.

8. The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals

The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals
Killington
10.0 out of 10, Exceptional, (1 review)
"Great amenitiesCleanNewAnd easy access to Starship Gondola at KillingtonWent with my two sons - we had a great time"
United States
Gifford F.
The price is ￥29,488
￥78,816 total
includes taxes & fees
Oct 28 - Oct 29
The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals
A living room with a wooden table, two chairs, a leather sofa, a coffee table, and a brick wall.

9. Liquid Lodge Lower: 2BR Duplex near Killington with 1 PM Checkout

Liquid Lodge Lower: 2BR Duplex near Killington with 1 PM Checkout
Killington
The price is ￥30,364
￥74,137 total
includes taxes & fees
Oct 28 - Oct 29
Liquid Lodge Lower: 2BR Duplex near Killington with 1 PM Checkout
A hot tub in a lush garden with a wooden deck and stairs leading to a cabin.

10. 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 Killington
Killington
9.0 out of 10, Wonderful, (7 reviews)
"Loved the quiet seclusion of the Shack, but also that we were close to hikes, lakes, markets, and food. We had a wonderful and relaxing stay!!"
United States
Sarah G.
The price is ￥28,466
￥81,537 total
includes taxes & fees
Oct 28 - Oct 29
Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington
A modern house with a stone facade, a large deck, and outdoor seating.

11. 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
9.0 out of 10, Wonderful, (6 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 dining area with a wooden table, four chairs, a coffee maker, and a trash can.

12. Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort

Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort
Chittenden
9.4 out of 10, Exceptional, (6 reviews)
"Loved this stay - the farmhouse is authentic and oozes charm! Everything about this stay was easy - 20min drive to the slopes, 15 min to downtown Rutland, and an extremely well-equipped house to easily accommodate the six of us. Superb communication from the host both prior to and during our stay (promptly answered several questions for us). If you want a vintage farmhouse feel as opposed to a modern condo-style stay, this is the place for you!"
United States
Carl P.
The price is ￥24,574
￥85,625 total
includes taxes & fees
Oct 28 - Oct 29
Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort
A hallway with a wooden beam ceiling, a door with a frosted glass panel, and a view of a living room with a sofa and a table.

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

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Comfortable stay but there was some noise in the bigger bedroom from the heating panels so the sleep was disturbed. Other than this, we had a great time at the accommodation."
Canada
Smriti
The price is ￥29,416
￥78,906 total
includes taxes & fees
Oct 28 - Oct 29
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
A wooden cabin with a hot tub in a corner, a sliding glass door leading to a living area, and a window with a view of greenery.

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

Private Killington Home w/ Indoor Hot Tub and 2 Living Rooms
North Sherburne
10.0 out of 10, Exceptional, (1 review)
"This company was professional and clear with their communication, very accommodating when we had to change plans. The house was in great shape and stocked with everything we needed"
United States
Kyle L.
The price is ￥73,508
￥157,392 total
includes taxes & fees
Oct 28 - Oct 29
Private Killington Home w/ Indoor Hot Tub and 2 Living Rooms
A modern kitchen with dark wood cabinets, a stainless steel refrigerator, a dining table with chairs, and a hanging light fixture.

15. 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.
The price is ￥32,262
￥98,948 total
includes taxes & fees
Oct 28 - Oct 29
Summit House on George | Renovated | 5 Mins to K-1 | Lift & Rental Deals
An indoor swimming pool with a wooden ceiling and large windows.

16. The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi

The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi
The Woods
The price is ￥21,855
￥55,717 total
includes taxes & fees
Nov 2 - Nov 3
The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi
A cozy living room with a stone fireplace, a large sectional sofa, and a wooden ceiling.

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

The Tower House | Hot Tub | Firepit | Dog-Friendly
Killington
6.8 out of 10, (3 reviews)
"Great place, near everything and great customer service!!"
United States
Patrick B.
The price is ￥38,747
￥116,285 total
includes taxes & fees
Oct 28 - Oct 29
The Tower House | Hot Tub | Firepit | Dog-Friendly
A cozy living room with a fireplace, a television, and a view of a snowy deck.

18. 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)
"Perfect for a large group or a couple of families."
United States
Mark B.
The price is ￥29,416
￥115,388 total
includes taxes & fees
Oct 28 - Oct 29
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
A spacious living room with a sofa, coffee table, and fireplace. There is a large window providing a view of the outdoors.

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)
"Great stay. Killer location!"
United States
Matthew P.
The price is ￥27,518
￥121,010 total
includes taxes & fees
Oct 30 - Oct 31
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
A cozy living room with a sectional sofa, a coffee table, and a fireplace.

20. Breakaway House: Killington Duplex, Unit A. Hot Tub Close to Resort.

Breakaway House: Killington Duplex, Unit A. Hot Tub Close to Resort.
Killington
7.6 out of 10, Good, (4 reviews)
"Great location, clean and quiet."
United States
Dr. Stephan B.
The price is ￥22,175
￥91,907 total
includes taxes & fees
Oct 28 - Oct 29
Breakaway House: Killington Duplex, Unit A. Hot Tub Close to Resort.
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

10/10 Excellent
"We enjoyed our stay at The Shire. We chose a room with a river view, so we were located in a nicely restored house located right next to the main Inn. Our room was very spacious, clean and comfortable. The location was perfect for walking into town, and a quick drive to the Marsh-Billings-Rockefeller National Historic Park."
Judy 1-night trip
Posted 9 hours ago
The Shire Woodstock

Find out more about Pittsfield

Pittsfield Vacation Homes information

Number of reviews
183
Accommodation
619 Vacation Homes
Lowest Price
￥43,316
Highest Price
￥157,392