Pittsfield Holiday Rentals

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Check prices for these dates

Tonight
4 Jul - 5 Jul
Tomorrow
5 Jul - 6 Jul
This weekend
4 Jul - 6 Jul
Next weekend
11 Jul - 13 Jul

Holiday Rentals in Pittsfield

Serene Architect-designed Vermont Chalet 4 Bedroom Home
Terrace/patio

Serene Architect-designed Vermont Chalet 4 Bedroom Home

3.5 star property
The price is HK$2,725
HK$6,546 total
includes taxes & fees
8 Jul - 9 Jul
Serene Architect-designed Vermont Chalet 4 Bedroom Home
Korean Gourmet Stay at Swiss Farm Inn - 1 night
Outdoor dining

Korean Gourmet Stay at Swiss Farm Inn - 1 night

The price is HK$3,139
HK$5,019 total
includes taxes & fees
8 Jul - 9 Jul
Korean Gourmet Stay at Swiss Farm Inn - 1 night
NEW! Serene Architect-Designed Vermont Chalet
Fridge, microwave, oven, dishwasher

NEW! Serene Architect-Designed Vermont Chalet

The price is HK$2,705
HK$6,624 total
includes taxes & fees
7 Jul - 8 Jul
NEW! Serene Architect-Designed Vermont Chalet
Peaceful oasis, stunning views, less than 10 mins from Woodstock Village
Interior

Peaceful oasis, stunning views, less than 10 mins from Woodstock Village

The price is HK$1,962
HK$4,008 total
includes taxes & fees
18 Jul - 19 Jul
Peaceful oasis, stunning views, less than 10 mins from Woodstock Village
Sleep Woodstock - Dog Friendly King Suite
Miscellaneous

Sleep Woodstock - Dog Friendly King Suite

The price is HK$865
HK$1,259 total
includes taxes & fees
7 Jul - 8 Jul
Sleep Woodstock - Dog Friendly King Suite
Sleep Woodstock - 2 Double Beds - Dog Friendly
Aerial view

Sleep Woodstock - 2 Double Beds - Dog Friendly

The price is HK$733
HK$1,113 total
includes taxes & fees
7 Jul - 8 Jul
Sleep Woodstock - 2 Double Beds - Dog Friendly
Sleep Woodstock Mobility Impaired Accessible Suite
Iron/ironing board, travel cot, WiFi, bed sheets

Sleep Woodstock Mobility Impaired Accessible Suite

The price is HK$733
HK$1,105 total
includes taxes & fees
21 Jul - 22 Jul
Sleep Woodstock Mobility Impaired Accessible Suite
A charming 1820's farmhouse
Interior

A charming 1820's farmhouse

10.0 out of 10, Exceptional, (26)
"this property had a very different feel because it was once an inn, which made it feel like we had the whole inn to ourselves, which was lovely. The place is spotless, everything you could possibly need is there, and it is beautifully decorated."
The price is HK$6,207
HK$10,403 total
includes taxes & fees
7 Jul - 8 Jul
A charming 1820's farmhouse
The Bridgewater House | Game Room | Hiking | Golf
Fridge, microwave, oven, stovetop

The Bridgewater House | Game Room | Hiking | Golf

9.4 out of 10, Exceptional, (6)
"My family enjoyed this house and there was plenty of space for sleeping and for the kids to play. Conveniently located for skiing at Killington."
The price is HK$1,664
HK$4,465 total
includes taxes & fees
23 Jul - 24 Jul
The Bridgewater House | Game Room | Hiking | Golf
Spacious country home, beautiful sunsets, 40 acres
Exterior

Spacious country home, beautiful sunsets, 40 acres

10.0 out of 10, Exceptional, (34)
"House was exactly as described in listing."
The price is HK$1,256
HK$4,069 total
includes taxes & fees
8 Jul - 9 Jul
Spacious country home, beautiful sunsets, 40 acres
Off Grid Glamping Shed with River Access
Property grounds

Off Grid Glamping Shed with River Access

2.0 star property
The price is HK$459
HK$734 total
includes taxes & fees
8 Jul - 9 Jul
Off Grid Glamping Shed with River Access
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Fridge, microwave, oven, stovetop

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

9.4 out of 10, Exceptional, (16)
"We celebrated my sister's 80th birthday at Blueberry Hill. It was very quiet, pleasant and perfect for our family."
The price is HK$1,436
HK$4,298 total
includes taxes & fees
15 Jul - 16 Jul
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
TV, fireplace

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

8.0 out of 10, Very good, (2)
"Great place for a ski weekend"
The price is HK$1,813
HK$4,093 total
includes taxes & fees
6 Jul - 7 Jul
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
RoundTop Chalet- Hot Tub, Grill, Hiking!
Outdoor spa tub

RoundTop Chalet- Hot Tub, Grill, Hiking!

The price is HK$1,898
HK$5,022 total
includes taxes & fees
7 Jul - 8 Jul
RoundTop Chalet- Hot Tub, Grill, Hiking!
107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool
Exterior

107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool

9.2 out of 10, Wonderful, (5)
"The check in process was so easy, our room was clean and had everything we needed. We would definitely stay here again"
The price is HK$816
HK$1,234 total
includes taxes & fees
5 Jul - 6 Jul
107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool
Queen Studio on the 2nd floor with outdoor heated pool 207
Interior

Queen Studio on the 2nd floor with outdoor heated pool 207

8.0 out of 10, Very good, (5)
"Overall a good option for a visit to Killington if you don’t need to be on the access road. The outdoor heated pool was a really nice way to relax after a day of skiing. If you don’t want to drive, there is a pretty good restaurant across the street. The only slight concern is if more units than unit 207 are listed on VRBO (the unit we stayed in). I’m glad we had an upstairs unit because the floor was very squeaky. I was wondering if it was annoying the unit below us. With that minor detail...
The price is HK$816
HK$1,234 total
includes taxes & fees
28 Jul - 29 Jul
Queen Studio on the 2nd floor with outdoor heated pool 207
Deluxe One Bedroom Queen Suite on the 2nd floor with outdoor heated pool 202
Fridge, microwave, oven, stovetop

Deluxe One Bedroom Queen Suite on the 2nd floor with outdoor heated pool 202

8.4 out of 10, Very good, (7)
"Very nice, comfortable and clean. Love the mini kitchen. Lots of space to move around."
The price is HK$906
HK$1,341 total
includes taxes & fees
20 Jul - 21 Jul
Deluxe One Bedroom Queen Suite on the 2nd floor with outdoor heated pool 202
Two Double bed Standard Hotel room 219
Interior

Two Double bed Standard Hotel room 219

7.6 out of 10, Good, (4)
"Very clean and easy access."
The price is HK$816
HK$1,234 total
includes taxes & fees
6 Jul - 7 Jul
Two Double bed Standard Hotel room 219
Two Double bed Hotel Room with outdoor heated pool 216
Interior

Two Double bed Hotel Room with outdoor heated pool 216

The price is HK$816
HK$1,234 total
includes taxes & fees
30 Jul - 31 Jul
Two Double bed Hotel Room with outdoor heated pool 216
Deluxe 1 bedroom suite located on first floor with outdoor heated pool 118/120
Interior

Deluxe 1 bedroom suite located on first floor with outdoor heated pool 118/120

10.0 out of 10, Exceptional, (2)
"This was a very nice quiet place. Loved the location and the room. Will definitely be going back."
The price is HK$1,154
HK$1,670 total
includes taxes & fees
14 Jul - 15 Jul
Deluxe 1 bedroom suite located on first floor with outdoor heated pool 118/120
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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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?

Spacious country home, beautiful sunsets, 40 acres: This holiday home rental outside of Pittsfield offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable 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.

How many holiday rentals are there in Pittsfield?

Expedia has 39 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.