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Check prices for these dates

In two weeks
12 Sep - 14 Sep
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov
In four months
19 Dec - 21 Dec

Vacation Homes in Pittsfield

Glamping hut with WiFi in Ripton, biking, hiking, skiing
Property grounds

Glamping hut with WiFi in Ripton, biking, hiking, skiing

The price is SAR 334
SAR 626 total
includes taxes & fees
31 Aug - 1 Sep
Glamping hut with WiFi in Ripton, biking, hiking, skiing
The Brandon Inn - King Room
Exterior

The Brandon Inn - King Room

8.4 out of 10, Very Good, (5)
"The Branford Inn was a historic hotel that despite its age was very nice."
The price is SAR 732
SAR 950 total
includes taxes & fees
10 Sep - 11 Sep
The Brandon Inn - King Room
Sleep Woodstock - 2 Double Beds - Dog Friendly
Iron/ironing board, travel crib, WiFi, bed sheets

Sleep Woodstock - 2 Double Beds - Dog Friendly

10.0 out of 10, Exceptional, (2)
"The property is exactly as represented. It’s super clean. Comfortable beds. Bathrooms are updated and nice. It’s right across from a beautiful river and close proximity to quaint downtown Woodstock or nearby Killington. Felt safe and homey. Great communication from property owner. Would recommend! "
The price is SAR 414
SAR 602 total
includes taxes & fees
1 Sep - 2 Sep
Sleep Woodstock - 2 Double Beds - Dog Friendly
Off Grid Glamping Shed with River Access
Property grounds

Off Grid Glamping Shed with River Access

2.0 star property
The price is SAR 220
SAR 351 total
includes taxes & fees
29 Aug - 30 Aug
Off Grid Glamping Shed with River Access
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Fridge, microwave, oven, stovetop

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

9.4 out of 10, Exceptional, (16)
"We celebrated my sister's 80th birthday at Blueberry Hill. It was very quiet, pleasant and perfect for our family."
The price is SAR 600
SAR 1,967 total
includes taxes & fees
2 Sep - 3 Sep
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
The Grizz- AC, Pool, Sauna, Gym, Near Resort
Golf

The Grizz- AC, Pool, Sauna, Gym, Near Resort

10.0 out of 10, Exceptional, (4)
"Place was overall great and just as advertised. Beds were awesome including the Murphy bed. Thanks for a wonderful weekend! I would definitely stay again. "
The Grizz- AC, Pool, Sauna, Gym, Near Resort
Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.
Fridge, microwave, oven, stovetop

Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.

2.0 star property
10.0 out of 10, Exceptional, (1)
"Such an awesome place! The booking/check-in process was seamless and the location cannot be beat! Will definitely be booking again. "
Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.
Luxury Condo Tucked in the Heart of Killington
Fridge, microwave, oven, stovetop

Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Hot Tub | Firepit | Dog-Friendly | Golf | Foliage
Outdoor spa tub

Hot Tub | Firepit | Dog-Friendly | Golf | Foliage

8.0 out of 10, Very Good, (1)
"Place was nice a cozy. Had a minor issue that was communicated quickly and resolved."
Hot Tub | Firepit | Dog-Friendly | Golf | Foliage
Peaceful oasis, stunning views, less than 10 mins from Woodstock Village
Interior

Peaceful oasis, stunning views, less than 10 mins from Woodstock Village

10.0 out of 10, Exceptional, (1)
"Beautiful, spacious, clean, relaxing home and property. Loved it! Would stay here again."
Peaceful oasis, stunning views, less than 10 mins from Woodstock Village
Ski home Mountain Views near Killington/Woodstock
Aerial view

Ski home Mountain Views near Killington/Woodstock

10.0 out of 10, Exceptional, (2)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
Ski home Mountain Views near Killington/Woodstock
Mad Mountain Meadows - Stunning Mountain Views!
Interior

Mad Mountain Meadows - Stunning Mountain Views!

10.0 out of 10, Exceptional, (1)
"Great house great location!"
Mad Mountain Meadows - Stunning Mountain Views!
Sleep Woodstock - Dog Friendly King Suite
Exterior

Sleep Woodstock - Dog Friendly King Suite

10.0 out of 10, Exceptional, (1)
"We had an excellent stay, everything was so clean, the room was well appointed and there was even a little communal area with laundry, kitchen, snacks, and shuffleboard. We would absolutely recommend this motel, it’s a gem! "
The price is SAR 473
SAR 671 total
includes taxes & fees
1 Sep - 2 Sep
Sleep Woodstock - Dog Friendly King Suite
Two Queen Bed Standard Hotel room with outdoor heated pool 201
TV, books, offices

Two Queen Bed Standard Hotel room with outdoor heated pool 201

8.6 out of 10, Excellent, (12)
"Our room was easy to find and very clean. And the late check-in was very helpful."
The price is SAR 429
SAR 637 total
includes taxes & fees
7 Sep - 8 Sep
Two Queen Bed Standard Hotel room with outdoor heated pool 201
Two Double Bed Standard Hotel Room with outdoor heated pool 101
Property grounds

Two Double Bed Standard Hotel Room with outdoor heated pool 101

8.2 out of 10, Very Good, (17)
"Room was just right for our 2 day ski trip to Killington. 5 minutes from gondola lift & access to the entire mountain. Plenty of food options close by also. Heated pool was an added bonus! A 12 year veteran was in agreement."
The price is SAR 429
SAR 637 total
includes taxes & fees
1 Sep - 2 Sep
Two Double Bed Standard Hotel Room with outdoor heated pool 101
CozyDen - AC, Grill, Bike to Mountain, Porch!
Fridge, microwave, oven, stovetop

CozyDen - AC, Grill, Bike to Mountain, Porch!

CozyDen - AC, Grill, Bike to Mountain, Porch!
Susan Lane Hideaway: 4BR/3.5BA Renovated Home. Close to skiing and town.
Dining

Susan Lane Hideaway: 4BR/3.5BA Renovated Home. Close to skiing and town.

9.0 out of 10, Wonderful, (4)
"Big and spacious. "
The price is SAR 743
SAR 2,294 total
includes taxes & fees
31 Aug - 1 Sep
Susan Lane Hideaway: 4BR/3.5BA Renovated Home. Close to skiing and town.
Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington
Outdoor spa tub

Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington

9.2 out of 10, Wonderful, (5)
"Our group was in town for an archery event nearby and the location was perfect. Its peaceful and quiet but close to everything. It is an older house but well taken care of. Would definitely recommend. "
The price is SAR 553
SAR 1,788 total
includes taxes & fees
1 Sep - 2 Sep
Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
Indoor pool, a heated pool

Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna

10.0 out of 10, Exceptional, (6)
"Great location and a great place. Felt right at home"
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