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
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Pittsfield holiday homes

Smart TV, offices

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, (1 review)
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
Interior

2. 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 €484
includes taxes & fees
17 Sept - 18 Sept
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Exterior

3. 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 €483
includes taxes & fees
17 Sept - 18 Sept
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Coffee/tea maker, fridge, microwave, oven

4. 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 €663
includes taxes & fees
27 Sept - 28 Sept
Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails
Coffee/tea maker, fridge, microwave, oven

5. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is €249
includes taxes & fees
29 Sept - 30 Sept
Luxury Condo Tucked in the Heart of Killington
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, (59 reviews)
"Perfect for a large group or a couple of families."
United States
Mark B.
The price is €13,574
includes taxes & fees
17 Sept - 18 Sept
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
TV, offices

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 price is €610
includes taxes & fees
17 Sept - 18 Sept
The Tower House | Hot Tub | Firepit | Dog-Friendly
TV, streaming services, music library, video library

8. 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 €525
includes taxes & fees
17 Sept - 18 Sept
Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
TV

9. Slopeside Estate Guesthouse: Hot tub, AC, Grill

Slopeside Estate Guesthouse: Hot tub, AC, Grill
Killington
The price is €823
includes taxes & fees
17 Sept - 18 Sept
Slopeside Estate Guesthouse: Hot tub, AC, Grill
Private kitchen

10. 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 €209
includes taxes & fees
28 Sept - 29 Sept
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Interior

11. CozyDen - AC, Bike to Mountain, Porch!

CozyDen - AC, 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 €224
includes taxes & fees
17 Sept - 18 Sept
CozyDen - AC, Bike to Mountain, Porch!
Iron/ironing board, free WiFi, bed sheets

12. 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
1 bedroom, desk, free WiFi, bed sheets

13. 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
Cozy Rutland Retreat
Interior

14. 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.
Snowarts- Game room, Fireplace, Close to golf!
Interior

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

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Killington
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Private kitchen

16. Hot Tub Getaway - Near Killington - Sleeps 12

Hot Tub Getaway - Near Killington - Sleeps 12
Killington
The price is €757
includes taxes & fees
22 Sept - 23 Sept
Hot Tub Getaway - Near Killington - Sleeps 12
Smart TV, fireplace

17. 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.
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
Terrace/patio

18. 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
Estelle Cottage- Private Sauna, Hot tub, Pool, AC
Smart TV, fireplace

19. 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.
Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole
Terrace/patio

20. The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.

The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
Killington
10.0 out of 10, Exceptional, (63 reviews)
"Great stay, everything was clean and location was amazing."
United States
John D.
The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
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

Brandon Inn

Brandon Inn

10/10 Excellent
"Clean room, friendly staff, great breakfast, fun unique rooms. This is an old remodeled building that is probably not a good place to stay if you have a hard time negotiating stairs. Other wise I think you will enjoy it."
Mark 1-night trip
Posted less than an hour ago
Brandon Inn

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
171
Accommodation
599 Holiday Homes
Lowest Price
€209
Highest Price
€13,574