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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

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

Spacious country home, beautiful sunsets, 40 acres
Exterior

Spacious country home, beautiful sunsets, 40 acres

10.0 out of 10, Exceptional, (32)
"Awsome place to stay for a week! "
The price is AED 533
AED 1,831 total
includes taxes & fees
30 May - 31 May
Spacious country home, beautiful sunsets, 40 acres
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Property grounds

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
Fridge, microwave, oven, stovetop

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
Off Grid Glamping Shed with River Access
Property grounds

Off Grid Glamping Shed with River Access

2.0 star property
The price is AED 239
AED 370 total
includes taxes & fees
30 May - 31 May
Off Grid Glamping Shed with River Access
Muwu in Killington Area with Jacuzzi
Terrace/patio

Muwu in Killington Area with Jacuzzi

The price is AED 1,010
AED 1,888 total
includes taxes & fees
2 Jun - 3 Jun
Muwu in Killington Area with Jacuzzi
BRIDGEWATER RETREAT
Exterior

BRIDGEWATER RETREAT

10.0 out of 10, Exceptional, (6)
"A true gem."
BRIDGEWATER RETREAT
Cute, Renovated Historic Home on River, Walk to Downtown
Fridge, microwave, oven, stovetop

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

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
Guest House surrounded by national forest
Interior

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
Fridge, microwave, oven, stovetop

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
The Bomoseen Bungalow: Vermont Lake House with Private Dock
Fridge, microwave, oven, stovetop

The Bomoseen Bungalow: Vermont Lake House with Private Dock

2.0 star property
The Bomoseen Bungalow: Vermont Lake House with Private Dock
Killington ski house
Fridge, microwave, oven, stovetop

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
Fridge, microwave, oven, stovetop

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
Exterior

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
Fridge, microwave, stovetop, coffee/tea maker

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!
Fridge, microwave, stovetop, dishwasher

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
TV, fireplace

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
Fridge, microwave, oven, stovetop

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
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Outdoor dining

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

8.4 out of 10, Very Good, (26)
"Basic ski house, in cool spot. 10 mins from bear mtn. Would definitely stay here again. "
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Sunburst home sleeps 18 with an indoor and outdoor hot tub. Perfect for family reunions and getaways.
Fridge, microwave, stovetop, dishwasher

Sunburst home sleeps 18 with an indoor and outdoor hot tub. Perfect for family reunions and getaways.

9.8 out of 10, Exceptional, (54)
"Spacious, clean, excellent property for families.2 hot ins and 2 livings rooms help give everyone their own space Fireplace creates cozy ambiance "
Sunburst home sleeps 18 with an indoor and outdoor hot tub. Perfect for family reunions and getaways.
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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