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

Villas in Pittsfield

No exact matches found, but these alternatives could be just right

Recommended hotels in Pittsfield

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

North Sherburne
10.0 out of 10, Exceptional, (1)
"Peak Hill, is a lovely and very clean home, with a fully stocked kitchen and comfy beds. This home is exactly as the pictures that are shown. We had a very small issue with the door lock (battery), called and it was fixed right away, wonderful service. The owner, Geri, we had the opportunity to meet and she is very kind and a pleasure to speak with. We travel alot and l bring pretty much my own kitchen, pillow...... with me where ever l go. However, l would of been fine using all at this...
United States
Essa R.
The price is SAR 693
SAR 2,089 total
includes taxes & fees
3 Dec - 4 Dec
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

The Getaway 4 Bedroom Home

3.0 star property
Pittsfield
The price is SAR 1,543
SAR 3,567 total
includes taxes & fees
3 Dec - 4 Dec
The Getaway 4 Bedroom Home

The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!

Pittsfield
The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!

My Place Hotel-Randolph VT

2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (337)
"Awesome staff and great room with Kitchenette"
United States
Mary
The price is SAR 376
SAR 410 total
includes taxes & fees
19 Dec - 20 Dec
My Place Hotel-Randolph VT

Sleep Woodstock Motel

2.0 star property
Woodstock
9.6 out of 10, Exceptional, (546)
"Clean, friendly, easy check in, welcoming accommodations. Can’t wait to come back"
United States
David
The price is SAR 290
SAR 484 total
includes taxes & fees
3 Dec - 4 Dec
Sleep Woodstock Motel

Grey Bonnet Inn

2.0 star property
Killington
7.8 out of 10, Good, (62)
"The bar was closed so that was a bummer. The room was clean, parking was right by my room and the location of the property is right next to the road I was traveling on. Somehow it was still very quiet!"
United States
Susan
The price is SAR 400
SAR 440 total
includes taxes & fees
3 Dec - 4 Dec
Grey Bonnet Inn

The Shire Woodstock

3.0 star property
Woodstock
8.8 out of 10, Excellent, (886)
"Upon entering the hotel, the lobby is gorgeous with 2 fireplaces. Staff was super friendly and the free breakfast was a bonus. The room was spotless and has a fireplace in the room. My wife and I loved this place and will definitely go back. "
United States
Vincent
The price is SAR 426
SAR 497 total
includes taxes & fees
17 Dec - 18 Dec
The Shire Woodstock

Comfort Inn Rutland - Killington

2.5 star property
Rutland
8.0 out of 10, Very Good, (1012)
"Clean, great steak house by the hotel"
United States
Caridad
The price is SAR 437
SAR 481 total
includes taxes & fees
10 Dec - 11 Dec
Comfort Inn Rutland - Killington

Mountain Valley Retreat

2.5 star property
Killington
9.6 out of 10, Exceptional, (189)
"Absolutely lovely stay!"
United States
Elizabeth
The price is SAR 413
SAR 467 total
includes taxes & fees
3 Dec - 4 Dec
Mountain Valley Retreat

Mountain Sports Inn

2.0 star property
The Woods
8.8 out of 10, Excellent, (977)
"This is a great place to stay. Attentive staff, easy parking, lots of options on the continental breakfast. "
United States
Lana
The price is SAR 372
SAR 409 total
includes taxes & fees
3 Dec - 4 Dec
Mountain Sports Inn

North Star Lodge and Resort

2.0 star property
Killington
8.6 out of 10, Excellent, (1005)
"Spotless room also very accommodating and friendly! Loved our short stay!"
United States
Candace
North Star Lodge and Resort

Hampton Inn Rutland

2.5 star property
Rutland
9.0 out of 10, Wonderful, (966)
"Very clean, good location, and super helpful staff!"
United States
Sheryl
The price is SAR 507
SAR 558 total
includes taxes & fees
8 Dec - 9 Dec
Hampton Inn Rutland

The Jackson

4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (256)
"Very cute inn, the restaurant was a plus. Had a great dinner there and def will come back. "
United States
Jaunita
The price is SAR 591
SAR 650 total
includes taxes & fees
3 Dec - 4 Dec
The Jackson

Mountain Meadows Lodge

3.5 star property
Killington
9.4 out of 10, Exceptional, (178)
"All round fantastic place to stay "
United Kingdom
Stephen
The price is SAR 615
SAR 770 total
includes taxes & fees
8 Dec - 9 Dec
Mountain Meadows Lodge

Turn of River Lodge

2.5 star property
Killington
8.8 out of 10, Excellent, (270)
"We enjoyed our stay. Close proximity to a lot of things to see and do. "
United States
Linda
The price is SAR 475
SAR 522 total
includes taxes & fees
8 Dec - 9 Dec
Turn of River Lodge

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 star property
Killington
7.4 out of 10, Good, (1004)
"It’s a small beautiful cabin like/feel hotel and they have everything you need and most esp a quick drive to Killington resort Their food is also very good and well prepared. "
United States
Cynthia
The price is SAR 551
SAR 606 total
includes taxes & fees
7 Dec - 8 Dec
Killington Mountain Lodge, Tapestry Collection by Hilton

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 SAR 367
SAR 404 total
includes taxes & fees
3 Dec - 4 Dec
Middlebury Sweets Motel

On The River Inn

4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1009)
"This place was charming!! Enjoyed everything about it and so much to do right there in the inn."
United States
Ross
The price is SAR 889
SAR 1,116 total
includes taxes & fees
5 Dec - 6 Dec
On The River Inn

Cortina Inn

3.0 star property
Rutland
6.6 out of 10, (645)
"location is excellent. As this is obviously an abandoned Holiday Inn, hopefully it is a renovation in progress."
United States
DICK
The price is SAR 371
SAR 409 total
includes taxes & fees
3 Dec - 4 Dec
Cortina Inn

Brandon Inn

3.0 star property
Brandon
8.8 out of 10, Excellent, (563)
"Enjoyed our stay at the Brandon Inn very much!"
United States
Lesley
The price is SAR 415
SAR 457 total
includes taxes & fees
3 Dec - 4 Dec
Brandon Inn
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.

White Friday Sale

Limited-time deals: Save up to 50% on select hotels
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.