Pittsfield Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Pittsfield holiday rentals

Smart TV, offices

NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
North Sherburne
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
TV

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

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
North Sherburne
10.0 out of 10, Exceptional, (1 review)
"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.
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
Outdoor dining

Glamping hut with WiFi in Ripton, biking, hiking, skiing

Glamping hut with WiFi in Ripton, biking, hiking, skiing
Ripton
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful, magical location, and prompt communication."
United States
Alex
The price is HK$697
HK$1,308 total
includes taxes & fees
2 Jun - 3 Jun
Glamping hut with WiFi in Ripton, biking, hiking, skiing
Property grounds

Secluded retreat in the trees

Secluded retreat in the trees
Roxbury
10.0 out of 10, Exceptional, (43 reviews)
"Great place…absolutely loved it! Clean, well appointed, and very helpful and friendly host. We plan on staying here again!"
United States
Jules
The price is HK$987
HK$1,896 total
includes taxes & fees
2 Jun - 3 Jun
Secluded retreat in the trees
Outdoor dining

Unique Vacation Rental in an Old Farmhouse in Windsor County, Vermont

Unique Vacation Rental in an Old Farmhouse in Windsor County, Vermont
South Royalton
The price is HK$1,016
HK$1,191 total
includes taxes & fees
7 Jun - 8 Jun
Unique Vacation Rental in an Old Farmhouse in Windsor County, Vermont
Terrace/patio

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Sharon
10.0 out of 10, Exceptional, (11 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
The price is HK$1,191
HK$2,484 total
includes taxes & fees
3 Jun - 4 Jun
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Private kitchen

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Mendon
9.8 out of 10, Exceptional, (6 reviews)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
United States
Aurore H.
The price is HK$1,011
HK$2,203 total
includes taxes & fees
2 Jun - 3 Jun
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Property grounds

Historic Converted Concrib Glamping Cabin in the Heart of Vermont, Perfect for a Weekend Retreat in Nature

Historic Converted Concrib Glamping Cabin in the Heart of Vermont, Perfect for a Weekend Retreat in Nature
South Royalton
The price is HK$1,862
HK$2,160 total
includes taxes & fees
12 Jun - 13 Jun
Historic Converted Concrib Glamping Cabin in the Heart of Vermont, Perfect for a Weekend Retreat in Nature
Fireplace, books

Stetson Hollow Cabin by Stetson Brook

Stetson Hollow Cabin by Stetson Brook
Warren
9.8 out of 10, Exceptional, (167 reviews)
"Perfect spot for our 3 day ski trip. Very nice and cozy cabin! Quiet area and the owners were great with making sure all was good. "
United States
Jeffrey C.
The price is HK$1,693
HK$3,449 total
includes taxes & fees
5 Jun - 6 Jun
Stetson Hollow Cabin by Stetson Brook
Interior

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Mendon
9.8 out of 10, Exceptional, (17 reviews)
"We wish there had been a recycle box. Also, mini split in living room didn’t work as well as the bedroom mini splits did for heat. Also, curtains/drapes on living room windows would be great and would help with heat loss."
United States
Jane
The price is HK$1,179
HK$3,511 total
includes taxes & fees
2 Jun - 3 Jun
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Property grounds

Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around

Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Hancock
10.0 out of 10, Exceptional, (4 reviews)
"The host was easy to communicate with, gracious and helpful. Amenities were generous and everything was in excellent condition. Really enjoyed the quiet treed setting and the hot tub."
United States
Elizabeth N.
The price is HK$1,192
HK$3,003 total
includes taxes & fees
14 Jun - 15 Jun
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Property grounds

Vermont Suite | 10 Min to Killington & Woodstock

Vermont Suite | 10 Min to Killington & Woodstock
Bridgewater
9.2 out of 10, Wonderful, (7 reviews)
"Overall, a great stay. "
United States
Meghan J.
The price is HK$580
HK$1,466 total
includes taxes & fees
2 Jun - 3 Jun
Vermont Suite | 10 Min to Killington & Woodstock
Fridge, microwave, oven, stovetop

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Leicester
10.0 out of 10, Exceptional, (77 reviews)
"Great place to stay for a Vermont getaway! "
United States
Jeremy H.
The price is HK$1,154
HK$1,766 total
includes taxes & fees
7 Jun - 8 Jun
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Fridge, microwave, oven, stovetop

Dreamy Artist Chalet in Secluded Historic Village

Dreamy Artist Chalet in Secluded Historic Village
East Warren
9.6 out of 10, Exceptional, (18 reviews)
"Loved the property. Clean, modern, great location."
United States
Richard
The price is HK$1,592
HK$3,231 total
includes taxes & fees
5 Jun - 6 Jun
Dreamy Artist Chalet in Secluded Historic Village
Dining

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (8 reviews)
"Very nice place to stay in Rutland."
United States
Dave M.
The price is HK$600
HK$1,482 total
includes taxes & fees
2 Jun - 3 Jun
Cozy Rutland Retreat
Fridge, microwave, oven, stovetop

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Killington
10.0 out of 10, Exceptional, (15 reviews)
"Host was very responsive and the home was great! "
United States
Rebecca B.
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Microwave, oven, stovetop, dishwasher

NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!

NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
Killington
10.0 out of 10, Exceptional, (2 reviews)
"Location near gondola was clutch (short 1 min drive). Super clean and layout of cabin was perfect for our group. We had a fair amount of snow and icy weather and our host kept the road and driveway clear."
United States
Jeremy F.
The price is HK$3,526
HK$6,827 total
includes taxes & fees
8 Jun - 9 Jun
NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
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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Top Pittsfield Hotel Reviews

Hampton Inn Rutland

Hampton Inn Rutland

10/10 Excellent
"Breakfast was plentiful and kitchen area was very clean. Pool and fitness room was clean as well as our room."
Arthur 3-night trip
Posted less than an hour ago
Hampton Inn Rutland

Find out more about Pittsfield

Search for holiday rentals in Pittsfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Pittsfield using one of the methods below:

  • View our selection of featured holiday rentals in Pittsfield
  • Use the map to find apartments and other holiday homes in the Pittsfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pittsfield while they last

Look no further and take a look at our great range of rental properties in Pittsfield!

Frequently asked questions

Can I find a holiday rental in Pittsfield?

Yes, there are holiday rentals close to the most popular sights in Pittsfield, or you can select a more secluded option if you're looking for a relaxing stay. Pittsfield is known for its bars and restaurants.

What are some of the best holiday rentals that Pittsfield has to offer?

Killington area home - 4-seasons, hot tub and A/C: This highly rated holiday home rental in Pittsfield is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Pittsfield?

Expedia has 30 holiday rentals for your stay in Pittsfield.

What can I see and do in Pittsfield?

While exploring the area, visit family-friendly sights like Killington Adventure Center, or get outside and enjoy nature at Green Mountain National Forest. Roger Clark Memorial Central Library and Pittsfield Town Hall are other places to visit while you're in town.

What are holiday rentals like in Pittsfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pittsfield. Holiday rentals offer extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family gatherings.