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

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

9.8 out of 10, Exceptional, (22)
"House is 1 minute or less from the Skye Peak Gondola, which as convenient for skiing. Clean house, has lots of room and games for families. Hot tub was really nice too."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont

10.0 out of 10, Exceptional, (2)
"The property was perfect for a Vermont getaway that will allow you to enjoy the autumn views and still give you the opportunity to engage in plenty of activities if you desire. Highly recommend this home!!"
Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont

Cozy Private Bedroom with Own Entrance - No Shower

10.0 out of 10, Exceptional, (3)
"This place is a nice, cozy little getaway. Great location!! Host has thought of every little accoutrement one might need when you're away from home, everything from hand lotion to a French press!! This was my second stay here, definitely won't be my last!! Love it!"
The price is AED 294
AED 448 total
includes taxes & fees
3 May - 4 May
Cozy Private Bedroom with Own Entrance - No Shower

Spacious country home, beautiful sunsets, 40 acres

10.0 out of 10, Exceptional, (32)
"House was exactly as described in listing."
The price is AED 496
AED 1,785 total
includes taxes & fees
29 Apr - 30 Apr
Spacious country home, beautiful sunsets, 40 acres

Classic Vermont Farmhouse near Sugarbush Resort

9.6 out of 10, Exceptional, (35)
"House is centrally located, old but in decent condition. Rooms are clean and updated. We enjoyed our stay"
Classic Vermont Farmhouse near Sugarbush Resort

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

9.2 out of 10, Wonderful, (36)
"Fantastic location for easy ski on ski off."
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi

10.0 out of 10, Exceptional, (3)
"Lovely rustic and cozy cabin stay"
Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi

The Shredquarters: Mid-Century Modern Chalet | 4 minutes to Snowshed 3BR/2BA

The price is AED 1,010
AED 2,229 total
includes taxes & fees
27 Apr - 28 Apr
The Shredquarters: Mid-Century Modern Chalet | 4 minutes to Snowshed 3BR/2BA

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

9.6 out of 10, Exceptional, (25)
"If you're looking for the perfect getaway near Killington, look no further than this incredible rental home! From the moment we stepped inside, we were blown away by how spacious and welcoming the property felt. It easily accommodated our large group, with plenty of room for everyone to relax and enjoy themselves.The home has such a cozy, homey atmosphere that made it hard to leave! We spent our evenings gathered around the real fireplace, which added so much warmth and charm to the experience....
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn

10.0 out of 10, Exceptional, (1)
"Was an amazing location with tons to do. Clean property and cozy!"
Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn

Off Grid Glamping Shed with River Access

2.0 star property
The price is AED 239
AED 370 total
includes taxes & fees
27 Apr - 28 Apr
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 for our guys weekend. Place was clean and beds were comfortable. Would definitely rent again."
Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola

Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen

9.8 out of 10, Exceptional, (32)
"Clean house with food amenities and great location."
Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen

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

8.6 out of 10, Excellent, (25)
"Cool location, perfect basic ski house"
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

9.6 out of 10, Exceptional, (119)
"The house was great for our large gathering of multiple families with kids. The commercial range with griddle was awesome and made cooking for the group so much easier. The house had multiple living spaces so it allowed a few in the group that had to work during the week to find a nice space away from the main group. Proximity to Killington was great!We were there during the Presidents Day holiday week so our check in got delayed (5pm) and check out was a bit early (10am), but totally...
Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

Spectacular 4 Bed Killington Home

9.8 out of 10, Exceptional, (118)
"This is our second year in a row renting this house. Plenty of room for 2 families of four and the location to Killington ski are is perfect. The wood stove is great for drying out ski gear and plenty of room for cooking and eating for 8. Communication with Wally was clear and responsive. Another great ski getaway!"
Spectacular 4 Bed Killington Home

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

9.8 out of 10, Exceptional, (53)
"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.

Historic Home w/glass house, mtn views, swim pond, near skiing, weekly discounts

10.0 out of 10, Exceptional, (82)
"Place was great. Spacious, clean and killer views. Kitchen is modern and well equipped making meals was easy. Very quiet location but still convenient to Killington/Pico. "
Historic Home w/glass house, mtn views, swim pond, near skiing, weekly discounts

FiddleHead Lane-Near Killington, Fireplace, Grill

10.0 out of 10, Exceptional, (3)
"We came up to Killington for a weekend of skiing and to enjoy all that the mountain has to offer. The house was perfect for our group. It was clean and comfortable. It had everything we needed and ample sleeping space. It was close enough to the mountain to get there quickly. The owners were extremely accommodating and always responded to any questions we had. They made us feel at home. We would definitely stay here again. "
FiddleHead Lane-Near Killington, Fireplace, Grill

Crisp and Clean Lakefront Home sleeps 8 in 4 Bedrooms

10.0 out of 10, Exceptional, (14)
"Such a nice weekend stay. We arrived late Friday night and woke up to a beautiful view of Lake Dunmore. The house was clean and welcoming. The kitchen had all one needed. The weather was not in our favor (rained most of the weekend) but it did not matter. It was a perfect spot for our quick weekend to Midd. "
Crisp and Clean Lakefront Home sleeps 8 in 4 Bedrooms
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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Other property types in Pittsfield

Killington area home - 4-seasons & hot tub. Sleeps 13+

9.8 out of 10, Exceptional, (117)
"We stayed at this property for a ski weekend in March. 8 guys fit comfortably and the accommodations were perfect. Property was as advertised and very clean. We enjoyed the hot tub after hitting the slopes which was a great way to finish the day. Owner was very accommodating and quick to reply to any inquiries or questions. 10/10"
Killington area home - 4-seasons & hot tub. Sleeps 13+

Private Killington Area Inn all to Yourself!

10.0 out of 10, Exceptional, (38)
"Eric is a perfect host! The inn is perfect, 9 rooms, private bathrooms. The kitchen is awesome, great appliances and big enough for everyone to be in the kitchen at the same time. This was our third year with family staying and celebrating. We will be back!"
Private Killington Area Inn all to Yourself!

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"This property was perfectly situated for ski on ski off accessibility. It had plenty of room for four adults. We also enjoyed the Sauna after skiing. The host Ryan was very easy to deal with and the check in/out process was simple and efficient. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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.