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
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Pittsfield holiday homes

Interior

1. 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 €513
includes taxes & fees
4 Aug - 5 Aug
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Exterior

2. 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 €513
includes taxes & fees
4 Aug - 5 Aug
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Coffee/tea maker, fridge, microwave, oven

3. 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 €660
includes taxes & fees
18 Aug - 19 Aug
Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails
Terrace/patio

4. 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
TV, offices

5. 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 €579
includes taxes & fees
24 Aug - 25 Aug
The Tower House | Hot Tub | Firepit | Dog-Friendly
TV, fireplace, Netflix, table football

6. 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, (56 reviews)
"Perfect for a large group or a couple of families."
United States
Mark B.
The price is €637
includes taxes & fees
3 Aug - 4 Aug
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
House, 2 Bedrooms | Private kitchen

7. Killington A-frame 2 Bedroom Home

Killington A-frame 2 Bedroom Home
3.0 star property
North Sherburne
The price is €604
includes taxes & fees
18 Aug - 19 Aug
Killington A-frame 2 Bedroom Home
Smart TV, fireplace, video games, stereo

8. 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, (19 reviews)
"Great location and excellent hosts "
United States
Peter G.
The price is €575
includes taxes & fees
2 Aug - 3 Aug
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
Interior

9. Snowarts- Game room, Fireplace, Close to golf!

Snowarts- Game room, Fireplace, Close to golf!
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 €772
includes taxes & fees
2 Aug - 3 Aug
Snowarts- Game room, Fireplace, Close to golf!
Interior

10. 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 €241
includes taxes & fees
4 Aug - 5 Aug
CozyDen - AC, Grill, Bike to Mountain, Porch!
Smart TV, fireplace

11. 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 €577
includes taxes & fees
2 Aug - 3 Aug
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
Outdoor spa tub

12. Classic Chalet w/Hot tub + king beds, Mtn 5 mins

Classic Chalet w/Hot tub + king beds, Mtn 5 mins
Killington
10.0 out of 10, Exceptional, (1 review)
"Great place. We had a great time. Also, major stores were not too far away if we needed anything"
United States
maria
The price is €640
includes taxes & fees
15 Aug - 16 Aug
Classic Chalet w/Hot tub + king beds, Mtn 5 mins
Smart TV, fireplace, video games, stereo

13. HappyCub- AC, Hot Tub, Fire Pit, Game Room!

HappyCub- AC, Hot Tub, Fire Pit, Game Room!
Killington
10.0 out of 10, Exceptional, (27 reviews)
"Great communication, location, and all around stay!"
United States
Ashley K.
HappyCub- AC, Hot Tub, Fire Pit, Game Room!
Interior

14. Walk to Pickle Barrel & Jax. Hot tub & Views

Walk to Pickle Barrel & Jax. Hot tub & Views
Killington
10.0 out of 10, Exceptional, (7 reviews)
"Great hosts with a great location to Killington"
United States
Ed P.
The price is €572
includes taxes & fees
15 Aug - 16 Aug
Walk to Pickle Barrel & Jax. Hot tub & Views
Smart TV, fireplace

15. Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole

Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole
Killington
10.0 out of 10, Exceptional, (6 reviews)
"Such a great spot."
United States
Kathleen G.
The price is €825
includes taxes & fees
4 Aug - 5 Aug
Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole
Exterior

16. BearRight- AC, Pool, Hot Tub, Grill, FirePit

BearRight- AC, Pool, Hot Tub, Grill, FirePit
Killington
9.8 out of 10, Exceptional, (13 reviews)
"Place was perfect for us for a group ski weekend."
United States
Kevin F.
The price is €761
includes taxes & fees
2 Aug - 3 Aug
BearRight- AC, Pool, Hot Tub, Grill, FirePit
TV, fireplace, streaming services, music library

17. Breakaway House: 6 BR/4 BA Duplex. Hot Tub. Perfect for families! Unit A & B

Breakaway House: 6 BR/4 BA Duplex. Hot Tub. Perfect for families! Unit A & B
Killington
9.0 out of 10, Wonderful, (6 reviews)
"Family friendly with all the amenities"
United States
Kalyani I.
Breakaway House: 6 BR/4 BA Duplex. Hot Tub. Perfect for families! Unit A & B
Smart TV, fireplace, DVD player, video library

18. 6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 10, Pet Friendly, Views & Grill

6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 10, Pet Friendly, Views & Grill
chittenden
10.0 out of 10, Exceptional, (32 reviews)
"We had a great time and enjoyed our stay."
United States
Nicole R.
The price is €811
includes taxes & fees
4 Aug - 5 Aug
6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 10, Pet Friendly, Views & Grill
6 bedrooms, desk, iron/ironing board, travel cot

19. DoubleDen- AC, Hot Tub, Fire pit, Grill, Game Room

DoubleDen- AC, Hot Tub, Fire pit, Grill, Game Room
Killington
10.0 out of 10, Exceptional, (26 reviews)
"Ver accommodating the property was amazing. "
United States
Jessica M.
DoubleDen- AC, Hot Tub, Fire pit, Grill, Game Room
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

Courtyard Middlebury

Courtyard Middlebury

8/10 Good
"The staff were very helpful. A repair of the toilet had to be done while we were there. It was done very quickly"
Linda 4-night trip
Posted 1 hour ago
Courtyard Middlebury

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
211
Accommodation
599 Holiday Homes
Lowest Price
€241
Highest Price
€1,209