Search Vacation Homes in Pittsfield

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Pittsfield

MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

10.0 out of 10, Exceptional, (72)
"We absolutely LOVED our stay. The house and all its amenities were perfect for our ski trip, and we would be thrilled to come back again some time. "
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

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

9.6 out of 10, Exceptional, (121)
"Another fun time at this well located, well appointed home."
Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

Spacious country home, beautiful sunsets, 40 acres

10.0 out of 10, Exceptional, (34)
"Awsome place to stay for a week! "
Spacious country home, beautiful sunsets, 40 acres

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

9.8 out of 10, Exceptional, (217)
"Our stay was amazing! The house offered everything we needed, was spacious and clean. Working with the owners was also easy. Would definitely recommend and stay again!"
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

The Brandon Inn - Fourth Floor Queen Room

8.4 out of 10, Very Good, (5)
"Clean, great location…restaurants, quaint interesting little shops… rent a vehicle and go hiking explore etc"
The price is AED 533
AED 689 total
includes taxes & fees
20 Jul - 21 Jul
The Brandon Inn - Fourth Floor Queen Room

Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon

10.0 out of 10, Exceptional, (58)
"Beautiful house right in the village. Easy access to both Sugarbush and Killington. Would definitely stay here again. "
Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon

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

Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

2.0 star property
9.8 out of 10, Exceptional, (75)
"Beautiful area and gorgeous leaves. Liked having a weber grill."
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

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

Off Grid Glamping Shed with River Access

2.0 star property
The price is AED 215
AED 344 total
includes taxes & fees
19 Jul - 20 Jul
Off Grid Glamping Shed with River Access

Ski-in/out sunrise condo with pool & hot tub - great ski retreat

8.8 out of 10, Excellent, (85)
"We had a great time. I would rent here again."
Ski-in/out sunrise condo with pool & hot tub - great ski retreat

Sleep Woodstock - 2 Double Beds - Dog Friendly

The price is AED 501
AED 703 total
includes taxes & fees
7 Aug - 8 Aug
Sleep Woodstock - 2 Double Beds - Dog Friendly

Private Ski Lodge with Giant Hot Tub Less Than Two Miles to Sugarbush!

9.8 out of 10, Exceptional, (46)
"Couldn’t ask for much more than this property. Perfect location near Sugar Bush, big beautiful hot tub and wood fireplace to relax by at the end of the night. Blend that with a huge kitchen to cook in and basement / rec room for the kids to call their own and it created an environment for the perfect week. Great location, great communication all around. "
Private Ski Lodge with Giant Hot Tub Less Than Two Miles to Sugarbush!

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

10.0 out of 10, Exceptional, (5)
Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont

Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail

9.2 out of 10, Wonderful, (67)
"we enjoyed staying there it was Ow same "
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail

The Bomoseen Bungalow: Vermont Lake House with Private Dock

2.0 star property
10.0 out of 10, Exceptional, (1)
"We Had a family gathering at Crystal Beach and this home was the perfect location for us"
The Bomoseen Bungalow: Vermont Lake House with Private Dock

Killington ski house

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

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!

Classic Vermont Farmhouse near Sugarbush Resort

9.8 out of 10, Exceptional, (37)
"House is centrally located, old but in decent condition. Rooms are clean and updated. We enjoyed our stay"
Classic Vermont Farmhouse near Sugarbush Resort
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.
Save an average of 15% on thousands of hotels when you're signed in