Pittsfield Holiday Rentals

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Holiday Rentals in Pittsfield

Korean Gourmet Stay at Swiss Farm Inn - 1 night

The price is AU$987
includes taxes & fees
24 July - 25 July
Korean Gourmet Stay at Swiss Farm Inn - 1 night

Off Grid Glamping Shed with River Access

2.0 star property
The price is AU$146
includes taxes & fees
4 Aug - 5 Aug
Off Grid Glamping Shed with River Access

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 AU$243
includes taxes & fees
5 Aug - 6 Aug
Queen Studio on the 2nd floor with outdoor heated pool 207

Two Double Bed Standard Hotel Room with outdoor heated pool 101

8.2 out of 10, Very good, (17)
"Room was just right for our 2 day ski trip to Killington. 5 minutes from gondola lift & access to the entire mountain. Plenty of food options close by also. Heated pool was an added bonus! A 12 year veteran was in agreement."
The price is AU$243
includes taxes & fees
5 Aug - 6 Aug
Two Double Bed Standard Hotel Room with outdoor heated pool 101

118 Two Double bed Standard Hotel room

9.0 out of 10, Wonderful, (2)
"We love staying here. So close to Killington, but also convenient. Clean, well maintained, and nicely furnished. Beautiful creek."
The price is AU$243
includes taxes & fees
30 July - 31 July
118 Two Double bed Standard Hotel room

Beautiful home located in the Mad River Valley

9.2 out of 10, Wonderful, (5)
"Good area"
Beautiful home located in the Mad River Valley

116 Two Double bed Standard Hotel room

8.6 out of 10, Excellent, (10)
"The place is good. It was our first time here and enjoyed our stay. The brook overlooking our window made the day"
The price is AU$243
includes taxes & fees
5 Aug - 6 Aug
116 Two Double bed Standard Hotel room

Beautiful home located in the Mad River Valley

9.8 out of 10, Exceptional, (19)
"We enjoyed our stay here. The property was 10 minutes from the Sugarbush resort, making it easy to catch the first lift of the day. It's also about a 5-minute drive from the historic Warran Village, which is worth walking around for a bit. Checking in and checking out was super easy. I would recommend to anyone looking for a no-frills stay that is super close to the mountain! "
Beautiful home located in the Mad River Valley

Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.

2.0 star property
10.0 out of 10, Exceptional, (1)
"Such an awesome place! The booking/check-in process was seamless and the location cannot be beat! Will definitely be booking again. "
The price is AU$840
includes taxes & fees
24 July - 25 July
Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.

The Grizz- AC, Pool, Sauna, Gym, Near Resort

10.0 out of 10, Exceptional, (4)
"Place was overall great and just as advertised. Beds were awesome including the Murphy bed. Thanks for a wonderful weekend! I would definitely stay again. "
The price is AU$682
includes taxes & fees
24 July - 25 July
The Grizz- AC, Pool, Sauna, Gym, Near Resort

Sleep Woodstock - Dog Friendly King Suite

10.0 out of 10, Exceptional, (1)
"We had an excellent stay, everything was so clean, the room was well appointed and there was even a little communal area with laundry, kitchen, snacks, and shuffleboard. We would absolutely recommend this motel, it’s a gem! "
The price is AU$251
includes taxes & fees
28 July - 29 July
Sleep Woodstock - Dog Friendly King Suite

CozyDen - AC, Grill, Bike to Mountain, Porch!

The price is AU$433
includes taxes & fees
24 July - 25 July
CozyDen - AC, Grill, Bike to Mountain, Porch!

Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington

9.6 out of 10, Exceptional, (4)
"Our group was in town for an archery event nearby and the location was perfect. Its peaceful and quiet but close to everything. It is an older house but well taken care of. Would definitely recommend. "
The price is AU$756
includes taxes & fees
24 July - 25 July
Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington

Two Double bed Standard Hotel room 219

7.6 out of 10, Good, (4)
"Very clean and easy access."
The price is AU$243
includes taxes & fees
5 Aug - 6 Aug
Two Double bed Standard Hotel room 219

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 AU$864
includes taxes & fees
28 July - 29 July
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Breakaway House: Renovated Killington Duplex, Unit A. Close to Resort.

7.6 out of 10, Good, (4)
"Great location, clean and quiet."
The price is AU$713
includes taxes & fees
24 July - 25 July
Breakaway House: Renovated Killington Duplex, Unit A. Close to Resort.

Beautiful home located in the Mad River Valley

9.8 out of 10, Exceptional, (37)
"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."
Beautiful home located in the Mad River Valley

Lakeside Lodge at Fern Lake: 3BR/1BA Waterfront w/ Dock

The price is AU$1,080
includes taxes & fees
24 July - 25 July
Lakeside Lodge at Fern Lake: 3BR/1BA Waterfront w/ Dock

Sleep Woodstock - Deluxe Suite

2.0 star property
The price is AU$636
includes taxes & fees
17 Aug - 18 Aug
Sleep Woodstock - Deluxe Suite

5-15 Minutes from Mountains, Balcony, Fireplace, Fast Wifi

The price is AU$483
includes taxes & fees
27 July - 28 July
5-15 Minutes from Mountains, Balcony, Fireplace, Fast Wifi
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

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 Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking: This holiday home rental outside of 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 7 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 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.