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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Pittsfield holiday 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, (1 review)
The price is AU$1,191
includes taxes & fees
27 Sept - 28 Sept
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.
The price is AU$1,154
includes taxes & fees
28 Sept - 29 Sept
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

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 AU$837
includes taxes & fees
28 Sept - 29 Sept
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.

4. 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 AU$830
includes taxes & fees
27 Sept - 28 Sept
Ski Home/Arcade Mountain Views Near Killington/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 AU$410
includes taxes & fees
29 Sept - 30 Sept
Luxury Condo Tucked in the Heart of Killington
A two-story house with a garage, solar panels, and a deck with outdoor furniture.

6. Secluded 5K Sq Ft Retreat: Sauna, Hot Tub & Games

Secluded 5K Sq Ft Retreat: Sauna, Hot Tub & Games
North Sherburne
9.4 out of 10, Exceptional, (24 reviews)
"House was beautiful & a great getaway for our group! "
United States
GiGi M.
The price is AU$1,111
includes taxes & fees
28 Sept - 29 Sept
Secluded 5K Sq Ft Retreat: Sauna, Hot Tub & Games
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.

7. 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 AU$401
includes taxes & fees
1 Oct - 2 Oct
CozyDen - AC, Bike to Mountain, Porch!
A cozy living room with a stone fireplace, a large sectional sofa, and a wooden ceiling.

8. 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 AU$1,065
includes taxes & fees
28 Sept - 29 Sept
The Tower House | Hot Tub | Firepit | Dog-Friendly
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 AU$340
includes taxes & fees
28 Sept - 29 Sept
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A dining table set with plates, glasses, and a vase with a plant.

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 AU$275
includes taxes & fees
26 Oct - 27 Oct
Cozy Rutland Retreat
A stone fireplace with a black mantel, framed picture, and decorative items.

11. 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 AU$1,202
includes taxes & fees
27 Sept - 28 Sept
Snowarts- Game room, Fireplace, Close to golf!
A cozy living room with a fireplace, a television, and a view of a snowy deck.

12. 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 AU$1,444
includes taxes & fees
28 Sept - 29 Sept
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
A bedroom with a bed, a nightstand, a window with a view of trees, and a framed picture on the wall.

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

Slopeside Estate Guesthouse: Hot tub, AC, Grill
Killington
The price is AU$1,359
includes taxes & fees
28 Sept - 29 Sept
Slopeside Estate Guesthouse: Hot tub, AC, Grill
A modern living room with a fireplace, a dining area, and a kitchen.

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

Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole
Killington
10.0 out of 10, Exceptional, (7 reviews)
"Such a great spot."
United States
Kathleen G.
The price is AU$1,344
includes taxes & fees
28 Sept - 29 Sept
Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole
A modern house with a stone facade, a large deck, and outdoor seating.

15. 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 AU$1,590
includes taxes & fees
27 Sept - 28 Sept
Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging
A two-story wooden cabin with a balcony, illuminated windows, and a front door.

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 AU$1,198
includes taxes & fees
30 Sept - 1 Oct
BearRight- AC, Pool, Hot Tub, Grill, FirePit
A covered porch with a grill, two Adirondack chairs, and a fire pit.

17. 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 AU$988
includes taxes & fees
20 Oct - 21 Oct
Estelle Cottage- Private Sauna, Hot tub, Pool, AC
A spacious kitchen with a large island, wooden dining table, and chairs. There are multiple windows providing natural light and views of the outdoors.

18. large ski ranch hot tub close to killington pets ok

large ski ranch hot tub close to killington pets ok
Mendon
9.0 out of 10, Wonderful, (8 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is AU$637
includes taxes & fees
28 Sept - 29 Sept
large ski ranch hot tub close to killington pets ok
A spacious kitchen with a central island, wooden ceiling, and large windows.

19. Hot Tub Getaway - Near Killington - Sleeps 12

Hot Tub Getaway - Near Killington - Sleeps 12
Killington
The price is AU$1,302
includes taxes & fees
28 Sept - 29 Sept
Hot Tub Getaway - Near Killington - Sleeps 12
A cozy living room with a stone fireplace, a sofa set, and a dining table.

20. 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
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

Emrose Luxury Cabins

Emrose Luxury Cabins

10/10 Excellent
"This is a unique property. Very clean, great shampoos, comfortable beds. Bring your own food and snacks. The grounds are super clean and in a safe, private area. We had an issue with the arrival instructions not opening in email but a call to the property phone number got our issue resolved quickly. Everything was great."
Sherry 1-night trip
Posted 9 hours ago
Emrose Luxury Cabins

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
129
Accommodation
605 Holiday Homes
Lowest Price
AU$275
Highest Price
AU$1,590