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Upfront pricingWe are not like the others - we include taxes and fees
Our top choices for Pittsfield vacation rentals
1. Ski Home/Arcade Mountain Views Near Killington/Woodstock
Ski Home/Arcade Mountain Views Near Killington/WoodstockStockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
Kevin M.
$452 nightly
The price is $506
Nov 9 - Nov 10
Total with taxes and fees
2. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/WoodstockStockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
Sophie L.
$452 nightly
The price is $506
Nov 9 - Nov 10
Total with taxes and fees
3. Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings
Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two KingsNorth Sherburne
8.0 out of 10, Very good, (17 reviews)
"We had a great time!"
Matthew R.
$331 nightly
The price is $374
Nov 9 - Nov 10
Total with taxes and fees
4. Gnome Home Mountain Ski Chalet w/Sauna Killington
Gnome Home Mountain Ski Chalet w/Sauna KillingtonStockbridge
10.0 out of 10, Exceptional, (7 reviews)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
Gerald S.
$432 nightly
The price is $453
Nov 10 - Nov 11
Total with taxes and fees
5. Luxury Condo Tucked in the Heart of Killington
Luxury Condo Tucked in the Heart of KillingtonKillington
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...
Melinda D.
$242 nightly
The price is $251
Nov 9 - Nov 10
Total with taxes and fees
6. The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531Killington
9.6 out of 10, Exceptional, (5 reviews)
"Place was great"
Nathan H.
$235 nightly
The price is $265
Nov 9 - Nov 10
Total with taxes and fees
7. Delightful 2-bedroom, solar-powered cabin in charming Vermont awaits you
Delightful 2-bedroom, solar-powered cabin in charming Vermont awaits youChittenden
$311 nightly
The price is $348
Nov 9 - Nov 10
Total with taxes and fees
8. Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532Killington
9.6 out of 10, Exceptional, (73 reviews)
"Cozy space close to the mountain. Host was very responsive and check in and check out was easy. "
Spencer P.
$373 nightly
The price is $421
Nov 9 - Nov 10
Total with taxes and fees
9. Jack S`Bearo - Slopes, Fireplace, Pool
Jack S`Bearo - Slopes, Fireplace, PoolKillington
10.0 out of 10, Exceptional, (17 reviews)
"Great condo and building. Everything in excellent condition. Convenient location."
Joseph S.
$232 nightly
The price is $262
Nov 9 - Nov 10
Total with taxes and fees
10. Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332Killington
9.4 out of 10, Exceptional, (12 reviews)
"Quick trip but would stay here again"
John O.
$387 nightly
The price is $437
Nov 9 - Nov 10
Total with taxes and fees
11. The Sunup Suite at Killington: 2RM/2BA Condo w/ Pool. Bus Route. Discounted Ski Rentals!
The Sunup Suite at Killington: 2RM/2BA Condo w/ Pool. Bus Route. Discounted Ski Rentals!Killington
10.0 out of 10, Exceptional, (1 review)
"We had a fantastic three-night stay at this cozy condo in Killington, perfect for our family of four. The location was ideal, just a short drive to the mountain, making it easy for us to hit the slopes each day. The accommodations were comfortable and well-equipped, providing a wonderful home base for our ski vacation!"
Catherine N.
$379 nightly
The price is $429
Nov 9 - Nov 10
Total with taxes and fees
12. Mountain Green ground-floor condo with private yard off the patio
Mountain Green ground-floor condo with private yard off the patioKillington
$248 nightly
The price is $280
Nov 11 - Nov 12
Total with taxes and fees
13. The Suites at Killington Center
The Suites at Killington CenterKillington
$427 nightly
The price is $470
Nov 10 - Nov 11
Total with taxes and fees
14. Robins Nest- FirePlace, Near Pico, Pool
Robins Nest- FirePlace, Near Pico, PoolKillington
10.0 out of 10, Exceptional, (4 reviews)
"Great location to Pico Mountain, clean, warm and spacious! "
Leslie D.
$547 nightly
The price is $595
Nov 9 - Nov 10
Total with taxes and fees
15. Modern Killington Farmhouse Condo: Close to it all! 412
Modern Killington Farmhouse Condo: Close to it all! 412Killington
10.0 out of 10, Exceptional, (62 reviews)
"Fantastic spot for hitting mountains as a family. Incredibly clean, convenience, and comfortable. Couldn’t be better! EV charging on site was the icing on the cake "
Tyler L.
$341 nightly
The price is $385
Nov 9 - Nov 10
Total with taxes and fees
16. Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5
Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5The Woods
10.0 out of 10, Exceptional, (15 reviews)
"Amazing location, great kitchen, my kids loved the hot tub, and it was a super easy process checking in and out. Will be staying here again!"
Keaton S.
$435 nightly
The price is $491
Nov 9 - Nov 10
Total with taxes and fees
17. Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to EverythingKillington
10.0 out of 10, Exceptional, (25 reviews)
"Great place "
Kathleen M.
$418 nightly
The price is $472
Nov 9 - Nov 10
Total with taxes and fees
18. FirBear- Pool, Gym, Fireplace, Hot tub!
FirBear- Pool, Gym, Fireplace, Hot tub!The Woods
9.8 out of 10, Exceptional, (25 reviews)
"Great place to stay for an escape to the mountains!"
Kristin G.
$334 nightly
The price is $377
Nov 10 - Nov 11
Total with taxes and fees
19. SnowCub- Pets Indoor Pool Hot Tub Sauna Fireplace
SnowCub- Pets Indoor Pool Hot Tub Sauna FireplaceThe Woods
10.0 out of 10, Exceptional, (27 reviews)
"Such a beautiful place to stay while in killington!!"
Brittany R.
$351 nightly
The price is $397
Nov 17 - Nov 18
Total with taxes and fees
20. Mountain Green high-floor front condo in Building 3 with ski trail views
Mountain Green high-floor front condo in Building 3 with ski trail viewsKillington
8.8 out of 10, Excellent, (47 reviews)
"Great location. Great amenities. Great communication. "
Jason B.
$322 nightly
The price is $364
Nov 11 - Nov 12
Total with taxes and fees
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.
Find vacation rentals that suit your style
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Top Pittsfield Hotel Reviews
Mountain Meadows Lodge
Mountain Meadows LodgeKillington
10/10 Excellent
Nice place. Close to the mountain. Nice aesthetic quaint and homey feel but also clean new and well kept. Hotel restaurant is a bit mediocre but not too bad. Good service so far on my trip too.
Timothy
