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Compare 626 Vacation Homes in Pittsfield with updated reviews, rates, and availability.

Spacious country home, beautiful sunsets, 40 acres

10.0 out of 10, Exceptional, (32)
"Awsome place to stay for a week! "
The price is SAR 525
SAR 1,848 total
includes taxes & fees
29 May - 30 May
Spacious country home, beautiful sunsets, 40 acres

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

9.8 out of 10, Exceptional, (22)
"Beautiful place."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

9.6 out of 10, Exceptional, (25)
"Absolutely loved it!!! Amazing house. Will definitely stay again!"
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

Muwu in Killington Area with Jacuzzi

The price is SAR 1,031
SAR 1,928 total
includes taxes & fees
2 Jun - 3 Jun
Muwu in Killington Area with Jacuzzi

BRIDGEWATER RETREAT

10.0 out of 10, Exceptional, (6)
"A true gem."
BRIDGEWATER RETREAT

Off Grid Glamping Shed with River Access

2.0 star property
The price is SAR 244
SAR 378 total
includes taxes & fees
29 May - 30 May
Off Grid Glamping Shed with River Access

Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola

9.6 out of 10, Exceptional, (20)
"Great place - very comfortable!!"
Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola

Cute, Renovated Historic Home on River, Walk to Downtown

9.6 out of 10, Exceptional, (9)
"I really enjoyed my month here in Brandon and 19 River. I would stay here again!"
Cute, Renovated Historic Home on River, Walk to Downtown

The Bomoseen Bungalow: Vermont Lake House with Private Dock

2.0 star property
The Bomoseen Bungalow: Vermont Lake House with Private Dock

Guest House surrounded by national forest

10.0 out of 10, Exceptional, (1)
"Beautiful house. Spectacular setting. Terrific hosts. "
Guest House surrounded by national forest

Middlebury Gem open concept and 5 minutes from town

10.0 out of 10, Exceptional, (71)
"Our second time staying here and once again it did not disappoint. Great location, spacious, and clean with all the amenities! Our family had a blast "
Middlebury Gem open concept and 5 minutes from town

Killington ski house

9.4 out of 10, Exceptional, (35)
"Property owner was excellent! We enjoyed our stay."
Killington ski house

FiddleHead Lane-Near Killington, Fireplace, Grill

10.0 out of 10, Exceptional, (3)
"My family of 8 stayed here for a ski vacation, and we loved it. Everything from the comfy beds, well equipped kitchen, space for ski equipment, and room for all of us to be together was perfect!! The hosts were Amazing! "
FiddleHead Lane-Near Killington, Fireplace, Grill

Killington Summer Retreat: Air Conditioned - Sleeps 8 - Fire Pit & Bike Shed

10.0 out of 10, Exceptional, (37)
"This home was clean, cozy, and perfectly located near the mountain and restaurants. It was the perfect fit for our group. Check-in was smooth, and the host was very responsive."
Killington Summer Retreat: Air Conditioned - Sleeps 8 - Fire Pit & Bike Shed

Valley View Retreat is a tastefully decorated home. Beautiful views

10.0 out of 10, Exceptional, (2)
"The home was so comfortable and had a gorgeous view of the mountains. It was so convenient to the ski slopes. Our family of 4 really enjoyed our stay."
Valley View Retreat is a tastefully decorated home. Beautiful views

Mendon Home w/ Hot Tub, Fire Pit & Near Skiing!

7.0 out of 10, Good, (2)
"This rental was not only clean and roomy but in a great spot. It was spacious throughout and the beds were comfortable. The backyard and hot tub were very nice too.. I would definitely stay again!"
Mendon Home w/ Hot Tub, Fire Pit & Near Skiing!

Lakefront home near ski resorts with water view, dock, deck, fireplaces, & W/D

8.6 out of 10, Excellent, (4)
"It was a great stay! Highly recommend "
Lakefront home near ski resorts with water view, dock, deck, fireplaces, & W/D

4 Season Secluded Lakefront Home near Ski Mountains

9.4 out of 10, Exceptional, (72)
"Property was clean, owners and property manager were very communicative. Property was clean, shoveled and plowed, and they were very accommodating with us arriving late. "
4 Season Secluded Lakefront Home near Ski Mountains

Classic Vermont Farmhouse near Sugarbush Resort

9.8 out of 10, Exceptional, (36)
"A perfect location for family weekend at Norwich University! We fit a family of 7 and all slept comfortably, lounged in the living room, or gathered in the spacious kitchen where I cooked and baked all weekend. We will definitely stay again!"
Classic Vermont Farmhouse near Sugarbush Resort

Rustic home with a private hot tub, fireplace, cable, & washer/dryer

9.4 out of 10, Exceptional, (55)
"This house is halfway between Killington and Okemoperfect locationgreat fireplacewould definitely stay again and recommend"
Rustic home with a private hot tub, fireplace, cable, & washer/dryer
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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