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.
The price is HK$1,764
HK$5,281 total
includes taxes & fees
28 May - 29 May
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
Fridge, oven, stovetop, coffee/tea maker

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$1,861
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$1,692
HK$3,457 total
includes taxes & fees
4 Jun - 5 Jun
Stetson Hollow Cabin by Stetson Brook
Exterior

Robert Frost Mountain Cabins

Robert Frost Mountain Cabins
3.5 star property
Ripton
10.0 out of 10, Exceptional, (41 reviews)
"Very nice place great owner"
United States
Joe
The price is HK$2,186
HK$2,383 total
includes taxes & fees
8 Jun - 9 Jun
Robert Frost Mountain Cabins
Property grounds

Secluded retreat in the trees

Secluded retreat in the trees
Roxbury
10.0 out of 10, Exceptional, (43 reviews)
"Very cozy and easy check in!"
United States
Emily R.
The price is HK$987
HK$1,887 total
includes taxes & fees
3 Jun - 4 Jun
Secluded retreat in the trees
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, (10 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
The price is HK$1,175
HK$2,501 total
includes taxes & fees
16 Jun - 17 Jun
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Exterior

Adorable cabin with screened porch and private fire pit

Adorable cabin with screened porch and private fire pit
Ripton
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful place to stay tucked away in the woods. The owners are extremely thoughtful and personable. Can’t wait to go back. "
United States
Sorin
The price is HK$2,005
HK$2,706 total
includes taxes & fees
28 May - 29 May
Adorable cabin with screened porch and private fire pit
Property grounds

Charming TREEHOUSE in remote location

Charming TREEHOUSE in remote location
Braintree
10.0 out of 10, Exceptional, (1 review)
The price is HK$2,490
HK$3,341 total
includes taxes & fees
1 Jun - 2 Jun
Charming TREEHOUSE in remote location
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$3,230 total
includes taxes & fees
4 Jun - 5 Jun
Dreamy Artist Chalet in Secluded Historic Village
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$6,826 total
includes taxes & fees
3 Jun - 4 Jun
NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
Interior

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Killington
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Interior

Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest

Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
Ripton
9.4 out of 10, Exceptional, (12 reviews)
"Our group booked this place for a ski trip to sugarbush. A remote area, but the cabin was very cool and our host were the best. The warm cinnamon twists in the morning were a big hit and the hot tub was perfect after a day of skiing. Would definitely look into booking this in the summer/fall. "
United States
John H.
The price is HK$2,005
HK$2,706 total
includes taxes & fees
28 May - 29 May
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
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$1,015
HK$1,191 total
includes taxes & fees
7 Jun - 8 Jun
Unique Vacation Rental in an Old Farmhouse in Windsor County, Vermont
Aerial view

Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (25 reviews)
"I enjoy the location "
United States
troy
The price is HK$1,849
HK$2,481 total
includes taxes & fees
10 Jun - 11 Jun
Mountain Green
Interior

Trail Creek: Ski home to renovated 1st floor, 1br condo. Sleeps 4.

Trail Creek: Ski home to renovated 1st floor, 1br condo. Sleeps 4.
Killington
10.0 out of 10, Exceptional, (83 reviews)
"Family have fun"
United States
Yanyi
The price is HK$3,134
HK$4,046 total
includes taxes & fees
24 Jun - 25 Jun
Trail Creek: Ski home to renovated 1st floor, 1br condo. Sleeps 4.
Smart TV, fireplace, DVD player, books

Charming and meticulously cleaned cabin with panoramic view of the Green Mtns

Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
Ripton
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful place. Lots to do around the cabin and in the area. The hosts are very helpful. The cabin has everything you could want for a great stay. "
United States
Susan
The price is HK$2,005
HK$2,706 total
includes taxes & fees
28 May - 29 May
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
Living area

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is HK$1,679
HK$6,204 total
includes taxes & fees
28 May - 29 May
Breakaway House by Killington Vacation Rentals
Dining

Trailside Village #8: Slopeside 3BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Trailside Village #8: Slopeside 3BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Killington
9.4 out of 10, Exceptional, (31 reviews)
"The condo was great. Clean, well appointed, and location was fantastic. No complaints, would stay here again. "
United States
Andrew F.
The price is HK$2,150
HK$6,141 total
includes taxes & fees
28 May - 29 May
Trailside Village #8: Slopeside 3BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Terrace/patio

BlueBird Escape- Pool, Near Bike Park and Golf!

BlueBird Escape- Pool, Near Bike Park and Golf!
Killington
The price is HK$2,250
HK$4,883 total
includes taxes & fees
28 May - 29 May
BlueBird Escape- Pool, Near Bike Park and Golf!
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

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

8/10 Good
"Was quiet it has parking and everything clean"
Edita 1-night trip
Posted 1 hour ago
Days Inn by Wyndham Rutland/Killington Area

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.