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

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, (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 €591
includes taxes & fees
1 Nov - 2 Nov
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.

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 €503
includes taxes & fees
4 Nov - 5 Nov
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Winter Wonderland

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 €476
includes taxes & fees
1 Nov - 2 Nov
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
A kitchen with a central island, two bar stools, pendant lights, and a view of the living area through an open archway.

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 €609
includes taxes & fees
11 Nov - 12 Nov
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.

5. 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 €233
includes taxes & fees
2 Nov - 3 Nov
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 €627
includes taxes & fees
1 Nov - 2 Nov
4BR Killington Home Perfect for Families, Pet-Friendly
An indoor swimming pool with a wooden ceiling and large windows.

7. 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 €331
includes taxes & fees
1 Nov - 2 Nov
The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi
A stone fireplace with a black mantel, framed picture, and decorative items.

8. 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 €740
includes taxes & fees
1 Nov - 2 Nov
SnowArts, Wood Burning fireplace, Close to slopes
A cozy living room with a fireplace, a television, and a view of a snowy deck.

9. 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 €642
includes taxes & fees
1 Nov - 2 Nov
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
A wooden interior with a bench and shelves, a door with a handle, and a tiled floor.

10. 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 €430
includes taxes & fees
1 Nov - 2 Nov
The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals
A spacious living room with a sofa, coffee table, and fireplace. There is a large window providing a view of the outdoors.

11. 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 €665
includes taxes & fees
1 Nov - 2 Nov
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
A cozy living room with a stone fireplace, a large sectional sofa, and a wooden ceiling.

12. 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 living room with a sectional sofa, a coffee table, and a fireplace.

13. 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 €490
includes taxes & fees
1 Nov - 2 Nov
Breakaway House: Killington Duplex, Unit A. Hot Tub Close to Resort.
A living room with a wooden table, two chairs, a leather sofa, a coffee table, and a brick wall.

14. 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 €423
includes taxes & fees
1 Nov - 2 Nov
Liquid Lodge Lower: 2BR Duplex near Killington with 1 PM Checkout
A dining area with a wooden table, four chairs, a coffee maker, and a trash can.

15. 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 €459
includes taxes & fees
1 Nov - 2 Nov
Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort
A hot tub in a lush garden with a wooden deck and stairs leading to a cabin.

16. 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 €434
includes taxes & fees
1 Nov - 2 Nov
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.

17. 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.
The price is €739
includes taxes & fees
3 Nov - 4 Nov
Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging
A spacious living room with a large sofa, a coffee table, and a patterned rug. There are multiple windows and a door leading to an outdoor deck.

18. Classic Killington Ski Chalet for 8 w/ Gear Room, 2 Fireplaces, 5 Mins to Slopes

Classic Killington Ski Chalet for 8 w/ Gear Room, 2 Fireplaces, 5 Mins to Slopes
Killington
Classic Killington Ski Chalet for 8 w/ Gear Room, 2 Fireplaces, 5 Mins to Slopes
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.

19. CozyDen- Fireplace, Ski Off/ Shuttle On

CozyDen- 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 €242
includes taxes & fees
9 Nov - 10 Nov
CozyDen- Fireplace, Ski Off/ Shuttle On
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.

20. 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 €412
includes taxes & fees
1 Nov - 2 Nov
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
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

8/10 Good
"It was clean and nice, but the bed was very hard and uncomfortable. I wouldn't recommend it for anyone who has an issue with stairs as the elevator is only used with the help of a staff member. There was also very little parking, The second night we had to park behind the dunkin down the street. I give it 4 stars overall, since it's an overall nice place. It would be 5 stars if they replace the mattresses."
Justin 2-night trip
Posted less than an hour ago
Brandon Inn

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
186
Accommodation
611 Holiday Homes
Lowest Price
€233
Highest Price
€740