Search Villas in Pittsfield

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months
No exact matches found, but these alternatives could be just right

Recommended hotels in Pittsfield

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (361)
"Friendly staff, clean, very comfortable room."
United States
Jennifer
The price is AED 389
AED 424 total
includes taxes & fees
25 Jan - 26 Jan
My Place Hotel-Randolph VT

Mountain Sports Inn

Mountain Sports Inn
2.0 star property
The Woods
8.8 out of 10, Excellent, (996)
"Staff was great and breakfast was excellent "
United States
Bruce
The price is AED 364
AED 400 total
includes taxes & fees
8 Jan - 9 Jan
Mountain Sports Inn

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (553)
"The staff at this motel are 5 star! Lisa went above and beyond to make my stay easy since I was there for a medical procedure. "
United States
Crystal
The price is AED 268
AED 524 total
includes taxes & fees
8 Jan - 9 Jan
Sleep Woodstock Motel

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (574)
"Clean room and staff was wonderful upon check in "
United States
Kaitlyn
The price is AED 409
AED 449 total
includes taxes & fees
8 Jan - 9 Jan
Brandon Inn

Mountain Valley Retreat

Mountain Valley Retreat
2.5 star property
Killington
9.6 out of 10, Exceptional, (192)
"This was my third stay with Mike and Barbara. It's just so lovely in a beautiful rural setting! And sure can't complain about the hearty breakfasts cooked by Chef Mike. It's certain I'll return on another ski adventure to Killington."
United States
Kathy
The price is AED 404
AED 457 total
includes taxes & fees
11 Jan - 12 Jan
Mountain Valley Retreat

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (982)
"clean, quiet, warm room. Comfortable beds."
United States
Margaret
The price is AED 603
AED 663 total
includes taxes & fees
14 Jan - 15 Jan
Hampton Inn Rutland

Turn of River Lodge

Turn of River Lodge
2.5 star property
Killington
9.0 out of 10, Wonderful, (271)
"Was amazing ill be back"
United States
Jacob
The price is AED 465
AED 511 total
includes taxes & fees
11 Jan - 12 Jan
Turn of River Lodge

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.0 out of 10, Very Good, (1014)
"Rooms were clean and comfortable.."
United States
Nimisha
The price is AED 515
AED 567 total
includes taxes & fees
1 Feb - 2 Feb
Comfort Inn Rutland - Killington

Killington Haus

Killington Haus
2.0 star property
Killington
9.0 out of 10, Wonderful, (2)
"Very clean, nature oriented furniture, pleasant place. Highly recommended. "
United States
Fellanza
The price is AED 626
AED 689 total
includes taxes & fees
8 Jan - 9 Jan
Killington Haus

Middlebury Sweets Motel

Middlebury Sweets Motel
2.5 star property
Middlebury
8.6 out of 10, Excellent, (388)
"Friendly staff, clean, comfortable and convenient to downtown. "
United States
Melissa
The price is AED 360
AED 396 total
includes taxes & fees
8 Jan - 9 Jan
Middlebury Sweets Motel

Greenbrier Inn

Greenbrier Inn
2.0 star property
Killington
9.4 out of 10, Exceptional, (650)
"Great location near the mountain, very cozy."
United States
Raphael
Greenbrier Inn

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 star property
Killington
7.4 out of 10, Good, (1000)
"Good place to stay when you ski"
United States
Josh
The price is AED 637
AED 701 total
includes taxes & fees
1 Feb - 2 Feb
Killington Mountain Lodge, Tapestry Collection by Hilton

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.6 out of 10, Exceptional, (187)
"Staff was amazing! They made the stay even better with their hospitality and overall service. I recommend this Lodge to anyone looking to go to Killington who wants a fun and relaxing stay. "
United States
Jaden
Mountain Meadows Lodge

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1006)
"Brilliant stay"
United States
Enrico
On The River Inn

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
8.8 out of 10, Excellent, (549)
"Laundry service was efficient and parking was easy "
United States
Agnes
The price is AED 459
AED 505 total
includes taxes & fees
13 Jan - 14 Jan
Courtyard Middlebury

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (899)
"Wonderful place to stay!"
United States
Robin
The price is AED 434
AED 516 total
includes taxes & fees
11 Jan - 12 Jan
The Shire Woodstock

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.6 out of 10, Excellent, (1001)
"Warm and cozy hotel."
United States
Tina
North Star Lodge and Resort

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (261)
"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
United States
Abby
The Jackson

The Trailside Inn

The Trailside Inn
3.0 star property
North Sherburne
9.0 out of 10, Wonderful, (141)
"The owners were terrific! The establishment was very clean & breakfast was delicious especially the oatmeal!!!"
United States
Kathleen
The price is AED 607
AED 667 total
includes taxes & fees
11 Jan - 12 Jan
The Trailside Inn

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (52)
"Charming bed and breakfast"
United States
Nicholas
The price is AED 565
AED 621 total
includes taxes & fees
14 Jan - 15 Jan
The Vesper
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

Top Pittsfield Hotel Reviews

Frequently asked questions

Why book your villa in Pittsfield with Expedia?
Booking a villa in Pittsfield is as simple as entering your travel dates and picking a place that suits your style. Seeking something budget friendly or upmarket, or a property that also comes with free WiFi? Use Expedia's search filters to narrow your results and find your perfect match.
How can I find cheap villas in Pittsfield?
With Expedia's filter tool, locating cheap villas in Pittsfield is a cinch. To discover accommodations that will keep some cash in your pocket, fine-tune your search by star rating, amenities and budget.