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

Search Holiday Homes in Pittsfield

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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 £539
includes taxes & fees
7 Oct - 8 Oct
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
10.0 out of 10, Exceptional, (1 review)
The price is £547
includes taxes & fees
7 Oct - 8 Oct
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
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 £498
includes taxes & fees
5 Oct - 6 Oct
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Winter Wonderland

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 £545
includes taxes & fees
18 Oct - 19 Oct
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
A wooden cabin with a snow-covered ground, a wooden fence, and a door with a window above it.

5. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is £223
includes taxes & fees
28 Oct - 29 Oct
Luxury Condo Tucked in the Heart of Killington
A spacious living room with a fireplace, a television, and a large window.

6. 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 £558
includes taxes & fees
5 Oct - 6 Oct
4BR Killington Home Perfect for Families, Pet-Friendly
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
6.8 out of 10, (3 reviews)
"Great place, near everything and great customer service!!"
United States
Patrick B.
The Tower House | Hot Tub | Firepit | Dog-Friendly
A cozy room with a wooden ceiling, a large window with a snowy view, a sofa, and a dining table with chairs.

8. Family and friend friendly upper ski cabin with bunks, sleeps 8

Family and friend friendly upper ski cabin with bunks, sleeps 8
Killington
Family and friend friendly upper ski cabin with bunks, sleeps 8
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 4 PM Checkout

Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout
Killington
Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout
A modern house with a stone facade, a large deck, and outdoor seating.

10. 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
9.6 out of 10, Exceptional, (5 reviews)
"Excellent, secluded location, super close to Killington. The property was very clean and everything seemed to work just fine. Water pressure in the bathroom sinks was strangely low, but shower pressure was good. Hot tub was wonderful after skiing all day.The host is amazing! Very attentive and proactive in reaching out with info. I'd definitely rent this house again!"
United States
Brett H.
The price is £820
includes taxes & fees
7 Oct - 8 Oct
Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging
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, (59 reviews)
"Perfect for a large group or a couple of families."
United States
Mark B.
The price is £720
includes taxes & fees
7 Oct - 8 Oct
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
A forested area with a wooden structure and a red and blue playset.

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, (72 reviews)
"Great stay. Killer location!"
United States
Matthew P.
The price is £658
includes taxes & fees
5 Oct - 6 Oct
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
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.

13. 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 £747
includes taxes & fees
5 Oct - 6 Oct
Private Killington Home w/ Indoor Hot Tub and 2 Living Rooms
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.

14. CozyDen- Location, Fireplace, Ski Off/ Shuttle On

CozyDen- Location, Fireplace, Ski Off/ Shuttle On
Killington
9.6 out of 10, Exceptional, (4 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is £228
includes taxes & fees
5 Oct - 6 Oct
CozyDen- Location, Fireplace, Ski Off/ Shuttle On
A stone fireplace with a black mantel, framed picture, and decorative items.

15. SnowArts, Wood Burning fireplace, Close to slopes

SnowArts, Wood Burning fireplace, Close to slopes
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 £716
includes taxes & fees
14 Oct - 15 Oct
SnowArts, Wood Burning fireplace, Close to slopes
A modern living room with a fireplace, a dining area, and a kitchen.

16. Alpine Chalet- Fireplace, Pool, Gym, At Pico

Alpine Chalet- Fireplace, Pool, Gym, At Pico
Killington
10.0 out of 10, Exceptional, (7 reviews)
"Such a great spot."
United States
Kathleen G.
The price is £709
includes taxes & fees
12 Oct - 13 Oct
Alpine Chalet- Fireplace, Pool, Gym, At Pico
A hot tub in a lush garden with a wooden deck and stairs leading to a cabin.

17. 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
9.4 out of 10, Exceptional, (6 reviews)
"We had a great time at this property! The hot tub was very clean, and the listing described it very well! "
United States
Briana S.
Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington
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.
The price is £911
includes taxes & fees
5 Oct - 6 Oct
Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining
A covered porch with a grill, two Adirondack chairs, and a fire pit.

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, (2 reviews)
"Yes!! King beds!! Tall people love king beds and they delivered. This does not diminish the fact that everything was excellent for our stay. From the welcome gifts including some great local coffee and syrup, to the relaxing sauna, the comfortable large living room and bedrooms, and all amenities, we wanted for nothing. Truly a gem on our whole vacation! We looked forward to returning in the late afternoon knowing we had a quiet evening and a good sleep ahead of us. Truly a great place to...
United States
Devin
The price is £533
includes taxes & fees
2 Nov - 3 Nov
Estelle Cottage- Private Sauna, Hot tub, Pool, AC
A modern kitchen with dark wood cabinets, a stainless steel refrigerator, a dining table with chairs, and a hanging light fixture.

20. 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.
Summit House on George | Renovated | 5 Mins to K-1 | Lift & Rental Deals
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

8/10 Good
"The hotel is clean. The staff is very helpful and pleasant. Coffee is offered 24/7 in the lobby. Unfortunately there is no free breakfast. They do have an option to have breakfast delivered to your door the night before and you cook it in your microwave. Plenty of parking. If you're visiting the Randolph area, it's a good place to stay. It's centrally located."
Marianne 2-night trip
Posted 3 hours ago
My Place Hotel-Randolph VT

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
186
Accommodation
604 Holiday Homes
Lowest Price
£223
Highest Price
£911