Pittsfield Holiday Rentals

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Check prices for these dates

Tonight
9 Jan - 10 Jan
Tomorrow
10 Jan - 11 Jan
This weekend
9 Jan - 11 Jan
Next weekend
16 Jan - 18 Jan

Our top choices for Pittsfield holiday rentals

Exterior
Off Grid Glamping Shed with River Access

Off Grid Glamping Shed with River Access

Off Grid Glamping Shed with River Access
2.0 star property
Randolph
10.0 out of 10, Exceptional, (1 review)
The price is HK$455
HK$728 total
includes taxes & fees
21 Jan - 22 Jan
Off Grid Glamping Shed with River Access
Property grounds
Secluded retreat in the trees

Secluded retreat in the trees

Secluded retreat in the trees
Roxbury
10.0 out of 10, Exceptional, (39 reviews)
"Idyllic setting, felt like I was home. "
United States
Karen R.
The price is HK$981
HK$1,831 total
includes taxes & fees
14 Jan - 15 Jan
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!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Sharon
10.0 out of 10, Exceptional, (5 reviews)
"Cabin was spotless and exactly what I expected"
United States
mark g.
The price is HK$925
HK$2,153 total
includes taxes & fees
13 Jan - 14 Jan
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
1 bedroom, iron/ironing board, travel cot, free WiFi
Cozy Cabin Retreat

Cozy Cabin Retreat

Cozy Cabin Retreat
Roxbury
10.0 out of 10, Exceptional, (33 reviews)
"Lovely, quiet & the BEST star gazing!!!"
United States
Jill F.
The price is HK$919
HK$1,657 total
includes taxes & fees
11 Jan - 12 Jan
Cozy Cabin Retreat
Property grounds
Vermont Suite | 10 Min to Killington & Woodstock

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$717
HK$1,628 total
includes taxes & fees
12 Jan - 13 Jan
Vermont Suite | 10 Min to Killington & Woodstock
Dining
Cozy Rutland Retreat

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.6 out of 10, Exceptional, (5 reviews)
"Peaceful stay in the city! We were headed to the rodeo, so this was the perfect distance away! "
United States
Aislinn F.
The price is HK$603
HK$1,470 total
includes taxes & fees
13 Jan - 14 Jan
Cozy Rutland Retreat
Property grounds
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
2.5 star property
Rutland
9.6 out of 10, Exceptional, (7 reviews)
The price is HK$1,176
HK$1,509 total
includes taxes & fees
21 Jan - 22 Jan
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
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

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$1,005
HK$2,190 total
includes taxes & fees
19 Jan - 20 Jan
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Interior
Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.6 out of 10, Exceptional, (40 reviews)
"The place was spacious, but small, which I loved! Plenty of hot water, great communication with owner, plenty of extra chairs and the leaf for the table was fantastic!"
United States
Michael M.
Beautiful home located in the Mad River Valley
Indoor pool
Clean & bright condo with mountain views & modern kitchen - walk to lifts

Clean & bright condo with mountain views & modern kitchen - walk to lifts

Clean & bright condo with mountain views & modern kitchen - walk to lifts
Killington
7.2 out of 10, Good, (45 reviews)
"Perfect place for a long weekend"
United States
Patrick D.
The price is HK$545
HK$2,162 total
includes taxes & fees
13 Jan - 14 Jan
Clean & bright condo with mountain views & modern kitchen - walk to lifts
Outdoor dining
Glamping hut with WiFi in Ripton, biking, hiking, skiing

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, (2 reviews)
"Super cute and cozy! It was perfect."
United States
Sarah D.
The price is HK$693
HK$1,299 total
includes taxes & fees
14 Jan - 15 Jan
Glamping hut with WiFi in Ripton, biking, hiking, skiing
Exterior
Killington Ski Resort VT Vacation Condos

Killington Ski Resort VT Vacation Condos

Killington Ski Resort VT Vacation Condos
3.5 star property
Killington
The price is HK$1,329
HK$3,011 total
includes taxes & fees
21 Jan - 22 Jan
Killington Ski Resort VT Vacation Condos
Fridge, microwave, oven, stovetop
Dreamy Artist Chalet in Secluded Historic Village

Dreamy Artist Chalet in Secluded Historic Village

Dreamy Artist Chalet in Secluded Historic Village
East Warren
9.2 out of 10, Wonderful, (10 reviews)
"Everything was beautiful. But for sure needs new mattress and pillows. "
United States
Jeanette R.
The price is HK$2,030
HK$3,617 total
includes taxes & fees
12 Jan - 13 Jan
Dreamy Artist Chalet in Secluded Historic Village
Exterior
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Killington
9.4 out of 10, Exceptional, (9 reviews)
"Great property, as advertised."
United States
Chris A.
The price is HK$951
HK$2,581 total
includes taxes & fees
15 Jan - 16 Jan
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
3 bedrooms, desk, iron/ironing board, travel cot
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Bridgewater
9.6 out of 10, Exceptional, (17 reviews)
"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "
United States
Gerri B.
The price is HK$1,613
HK$4,556 total
includes taxes & fees
12 Jan - 13 Jan
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Property grounds
Gnome Home Mountain Ski Chalet w/Sauna Killington

Gnome Home Mountain Ski Chalet w/Sauna Killington

Gnome Home Mountain Ski Chalet w/Sauna Killington
Stockbridge
10.0 out of 10, Exceptional, (4 reviews)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
The price is HK$2,211
HK$4,562 total
includes taxes & fees
12 Jan - 13 Jan
Gnome Home Mountain Ski Chalet w/Sauna Killington
Exterior
Robert Frost Mountain Cabins

Robert Frost Mountain Cabins

Robert Frost Mountain Cabins
3.5 star property
Ripton
10.0 out of 10, Exceptional, (40 reviews)
"Ammazing,would go again!"
United States
Joseph
The price is HK$2,020
HK$2,202 total
includes taxes & fees
12 Jan - 13 Jan
Robert Frost Mountain Cabins
Property grounds
Doc's Lake house 1st floor, 2 bedroom apartment

Doc's Lake house 1st floor, 2 bedroom apartment

Doc's Lake house 1st floor, 2 bedroom apartment
Salisbury
10.0 out of 10, Exceptional, (73 reviews)
"Doc runs a great place for all to enjoy. "
United States
William D.
The price is HK$1,051
HK$1,570 total
includes taxes & fees
15 Jan - 16 Jan
Doc's Lake house 1st floor, 2 bedroom apartment
TV
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
Killington
9.4 out of 10, Exceptional, (64 reviews)
"Condo well equipped- hosts very responsive-pool area great! "
United States
gail m.
The price is HK$1,115
HK$2,440 total
includes taxes & fees
12 Jan - 13 Jan
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
Fridge, microwave, oven, stovetop
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

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, (69 reviews)
"Very pleasant stay, at a unique and interesting property."
United States
Steve P.
The price is HK$1,012
HK$1,578 total
includes taxes & fees
19 Jan - 20 Jan
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
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

Mountain Meadows Lodge

Mountain Meadows Lodge

10/10 Excellent
"We had a great stay at Mountain Meadows lodge for 5 nights! The staff was very friendly, there were free snowshoe and sled rentals, a ski boot dryer, a wonderful jacuzzi and sauna, a fun game room with free games, various hot breakfast, a hammock outside, and cozy, freshly renovated clean interior. We will definitely come back! This is one of the best hotels we have stayed at in Vermont!"
IRINA 5-night trip
Posted 2 days ago
Mountain Meadows Lodge

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, Vermont Ski House w/ Hot Tub and Sauna: This holiday home rental outside Pittsfield is located in the mountains, and has a balcony, 1 hot tub and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of books in this rental home to help you unwind.

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.