Pittsfield Holiday Rentals

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Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Holiday Rentals in Pittsfield

Fridge, microwave, oven, stovetop
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Holiday Home in 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 HK$1,439
HK$4,378 total
includes taxes & fees
24 Nov - 25 Nov
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
Exterior
The Getaway 4 Bedroom Home

Holiday Home in Pittsfield

3.0 star property
The price is HK$3,238
HK$7,446 total
includes taxes & fees
22 Nov - 23 Nov
The Getaway 4 Bedroom Home
Exterior
The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!

Holiday Home in Pittsfield

The price is HK$2,569
HK$6,364 total
includes taxes & fees
25 Nov - 26 Nov
The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!
Property grounds
Glamping hut with WiFi in Ripton, biking, hiking, skiing

Camping in Ripton

10.0 out of 10, Exceptional, (2)
"Super cute and cozy! It was perfect."
United States
Sarah D.
The price is HK$693
HK$1,299 total
includes taxes & fees
5 Dec - 6 Dec
Glamping hut with WiFi in Ripton, biking, hiking, skiing
Property grounds
Off Grid Glamping Shed with River Access

Holiday Home in Randolph

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is HK$455
HK$728 total
includes taxes & fees
23 Nov - 24 Nov
Off Grid Glamping Shed with River Access
Property grounds
Beautiful home located in the Mad River Valley

Holiday Home in Warren

10.0 out of 10, Exceptional, (22)
"Had a wonderful stay "
United States
Yang O.
Beautiful home located in the Mad River Valley
Exterior
Mountain Green Resort by Killington VR - 1 Bedrooms

Condo in Killington

3.5 star property
The price is HK$1,034
HK$3,460 total
includes taxes & fees
23 Nov - 24 Nov
Mountain Green Resort by Killington VR - 1 Bedrooms
Exterior
Killington Studio: Great Location! Comfy. 431

Condo in Killington

8.8 out of 10, Excellent, (5)
"Great place to stay!"
United States
Carla M.
The price is HK$531
HK$1,767 total
includes taxes & fees
24 Nov - 25 Nov
Killington Studio: Great Location! Comfy. 431
Exterior
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A

Condo in Killington

9.2 out of 10, Wonderful, (5)
"I don’t think I’ve ever had such wonderful service checking in and caring for our needs. Amazing response time and outstanding stay. Thank you."
United States
Margaret L.
The price is HK$608
HK$1,823 total
includes taxes & fees
24 Nov - 25 Nov
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A
Interior
Ben & Jerry Suite | Skiing | Hiking | Biking

Apartment in Bridgewater

9.2 out of 10, Wonderful, (7)
"Close to Woodstock and market. Easy check in. Very quiet. Kurig, no cups for coffee."
United States
Nancy
The price is HK$623
HK$1,507 total
includes taxes & fees
1 Dec - 2 Dec
Ben & Jerry Suite | Skiing | Hiking | Biking
Exterior
Robert Frost Mountain Cabins

Cabin in Ripton

3.5 star property
10.0 out of 10, Exceptional, (40)
"Ammazing,would go again!"
United States
Joseph
The price is HK$1,976
HK$2,154 total
includes taxes & fees
25 Nov - 26 Nov
Robert Frost Mountain Cabins
Interior
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Condo in Killington

9.6 out of 10, Exceptional, (4)
"The place was clean and easy to get to. "
United States
Sarah Z.
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
Indoor pool
The Powder Pad Studio - Perfect for Two - On Shuttle Route w/ Amenities A4A

Condo in Killington

The price is HK$651
HK$1,882 total
includes taxes & fees
24 Nov - 25 Nov
The Powder Pad Studio - Perfect for Two - On Shuttle Route w/ Amenities A4A
Terrace/patio
Killington condo 5 min to killington resort

Condo in Killington

9.4 out of 10, Exceptional, (8)
"We loved staying here. It was comfortable, had everything we needed. 100% would stay here again!"
United States
Vanessa O.
The price is HK$694
HK$2,393 total
includes taxes & fees
25 Nov - 26 Nov
Killington condo 5 min to killington resort
Fridge, microwave, oven, stovetop
Luxury Condo Tucked in the Heart of Killington

Holiday Home in Killington

8.0 out of 10, Very good, (1)
"The condo was in a beautiful location but was rather isolated from grocery and dining options. Our host was good at communicating however we received a message about the fireplace not being available to us a day before we came and we got there in the dark with no lights on. The condo itself could not really be called "luxury" as it was dated and lacked some basics like soap in the bathroom, a towel hook in the 1/2 bath, kleenex, cracked dishes, etc. Liked that it was near a waterfall and hiking...
United States
Dean
The price is HK$925
HK$2,529 total
includes taxes & fees
25 Nov - 26 Nov
Luxury Condo Tucked in the Heart of Killington
Property grounds
Beautiful home located in the Mad River Valley

Holiday Home in Warren

9.8 out of 10, Exceptional, (39)
"We had a great time staying at this house during our Sugarbush skiing trip this February. The place is easy to access and is close to the ski resort. The house had everything we needed for a comfortable stay. I highly recommend this rental."
United States
Dmitriy K.
Beautiful home located in the Mad River Valley
Exterior
Killington Blue Studio: Sleeps 4, Close to Mtn 123

Condo in Killington

9.4 out of 10, Exceptional, (9)
"Great location and clean property"
United States
KEVIN C.
The price is HK$531
HK$1,767 total
includes taxes & fees
24 Nov - 25 Nov
Killington Blue Studio: Sleeps 4, Close to Mtn 123
Property grounds
5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

Holiday Home in granville

9.4 out of 10, Exceptional, (83)
"Great place! Comfortable and conveniently located. "
United States
Violet R.
The price is HK$701
HK$2,362 total
includes taxes & fees
23 Nov - 24 Nov
5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush
Property grounds
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Cabin in Sharon

10.0 out of 10, Exceptional, (3)
"Very welcoming, awesome weekend getaway."
United States
Zachary B.
The price is HK$818
HK$2,023 total
includes taxes & fees
3 Dec - 4 Dec
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Fridge, microwave, oven, stovetop
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

Cottage in Mendon

2.0 star property
9.8 out of 10, Exceptional, (11)
"Very clean, and just the perfect getaway. Private and quaint, but close enough to amenities. A very pleasant stay indeed."
United States
Linda B.
The price is HK$1,062
HK$3,376 total
includes taxes & fees
24 Nov - 25 Nov
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
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

On The River Inn

On The River Inn

10/10 Excellent
"Hands down one of the best places I have ever stayed. Beautiful view, great room and very cozy no matter where you were in the inn."
Harvey 1-night trip
Posted 2 days ago
On The River Inn

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
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  • 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 Mountain Home! HotTub & 5 min to Skiing! by RedAwning: This holiday home rental outside of Pittsfield is located near skiing, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and an oven. You can relax into your holiday with 1 hot tub and table football.

How many holiday rentals are there in Pittsfield?

Expedia has 29 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.