Holiday Homes in Pittsfield

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Our top choices for Pittsfield holiday homes

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 AU$877
includes taxes & fees
15 Nov - 16 Nov
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

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, (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 AU$952
includes taxes & fees
15 Nov - 16 Nov
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

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 AU$815
includes taxes & fees
15 Nov - 16 Nov
Ski Home/Arcade Mountain Views Near Killington/Woodstock

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 AU$815
includes taxes & fees
15 Nov - 16 Nov
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

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 AU$335
includes taxes & fees
15 Nov - 16 Nov
Luxury Condo Tucked in the Heart of Killington

6. 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 AU$670
includes taxes & fees
15 Nov - 16 Nov
Liquid Lodge Lower: 2BR Duplex near Killington with 1 PM Checkout

7. Barrows Ridge Chalet | Mountain Views, Private Hot Tub, 4 Bedrooms

Barrows Ridge Chalet | Mountain Views, Private Hot Tub, 4 Bedrooms
Killington
The price is AU$1,196
includes taxes & fees
15 Nov - 16 Nov
Barrows Ridge Chalet | Mountain Views, Private Hot Tub, 4 Bedrooms

8. 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 AU$705
includes taxes & fees
15 Nov - 16 Nov
Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington

9. 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 AU$1,244
includes taxes & fees
15 Nov - 16 Nov
Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging

10. 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$1,150
includes taxes & fees
15 Nov - 16 Nov
The Tower House | Hot Tub | Firepit | Dog-Friendly

11. 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 AU$529
includes taxes & fees
15 Nov - 16 Nov
The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi

12. 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.
Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.

13. 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)
"It was a great stay with the family!!"
United States
Mary C.
The price is AU$1,208
includes taxes & fees
15 Nov - 16 Nov
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.

14. Private Killington Home w/ Indoor Hot Tub and 2 Living Rooms

Private Killington Home w/ Indoor Hot Tub and 2 Living Rooms
North Sherburne
10.0 out of 10, Exceptional, (1 review)
"This company was professional and clear with their communication, very accommodating when we had to change plans. The house was in great shape and stocked with everything we needed"
United States
Kyle L.
The price is AU$1,338
includes taxes & fees
15 Nov - 16 Nov
Private Killington Home w/ Indoor Hot Tub and 2 Living Rooms

15. 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 AU$1,659
includes taxes & fees
15 Nov - 16 Nov
Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining

16. 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.
The price is AU$845
includes taxes & fees
15 Nov - 16 Nov
Summit House on George | Renovated | 5 Mins to K-1 | Lift & Rental Deals

17. 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
The price is AU$1,377
includes taxes & fees
15 Nov - 16 Nov
Classic Killington Ski Chalet for 8 w/ Gear Room, 2 Fireplaces, 5 Mins to Slopes

18. 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 AU$793
includes taxes & fees
15 Nov - 16 Nov
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

19. 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 AU$1,242
includes taxes & fees
16 Nov - 17 Nov
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

20. 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 AU$1,198
includes taxes & fees
13 Nov - 14 Nov
SnowArts, Wood Burning fireplace, Close to slopes
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.

Learn more about Pittsfield

Nestled in Vermont's Green Mountains, Pittsfield offers excellent hiking on the Long Trail and thrilling mountain biking at Green Mountain Trails. Riverside picnics along the Tweed River provide peaceful breaks between seasonal activities at nearby Killington Resort.

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

Top reviews in Pittsfield