Pittsfield Holiday Rentals

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Our top choices for Pittsfield holiday rentals

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 AU$895
includes taxes & fees
19 Jan - 20 Jan
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
2.0 star property
The price is AU$1,010
includes taxes & fees
19 Jan - 20 Jan
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
2.0 star property
10.0 out of 10, Exceptional, (1 review)
The price is AU$142
includes taxes & fees
14 Jan - 15 Jan
Off Grid Glamping Shed with River Access
7.2 out of 10, Good, (45 reviews)
"Perfect place for a long weekend"
United States
Patrick D.
The price is AU$448
includes taxes & fees
10 Feb - 11 Feb
Clean & bright condo with mountain views & modern kitchen - walk to lifts
9.2 out of 10, Wonderful, (7 reviews)
"Overall, a great stay. "
United States
Meghan J.
The price is AU$316
includes taxes & fees
19 Jan - 20 Jan
Vermont Suite | 10 Min to Killington & Woodstock

Apartment in Rutland

Cozy Rutland Retreat
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 AU$281
includes taxes & fees
14 Jan - 15 Jan
Cozy Rutland Retreat
10.0 out of 10, Exceptional, (5 reviews)
"Cabin was spotless and exactly what I expected"
United States
mark g.
The price is AU$478
includes taxes & fees
5 Feb - 6 Feb
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
10.0 out of 10, Exceptional, (39 reviews)
"Wonderful location and property. Hosts were welcoming and we had a comfortable stay. Hannah shared a bunch of local recommendations and tips! We had a great getaway!"
United States
Niti P.
The price is AU$354
includes taxes & fees
14 Jan - 15 Jan
Secluded retreat in the trees
3.5 star property
10.0 out of 10, Exceptional, (40 reviews)
"Ammazing,would go again!"
United States
Joseph
The price is AU$417
includes taxes & fees
14 Jan - 15 Jan
Robert Frost Mountain Cabins

Cottage in Roxbury

Cozy Cabin Retreat
10.0 out of 10, Exceptional, (33 reviews)
"Lovely, quiet & the BEST star gazing!!!"
United States
Jill F.
The price is AU$319
includes taxes & fees
14 Jan - 15 Jan
Cozy Cabin Retreat
9.0 out of 10, Wonderful, (7 reviews)
"Great room, plenty of amenities, close to restaurants and mountains"
United States
Daniel T.
The price is AU$280
includes taxes & fees
15 Jan - 16 Jan
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
8.4 out of 10, Very good, (33 reviews)
"Great stay!"
United States
Bryann F.
The price is AU$525
includes taxes & fees
21 Jan - 22 Jan
Comfortable mountain gem with pool, mountain views, & indoor parking space
3.5 star property
The price is AU$487
includes taxes & fees
14 Jan - 15 Jan
Killington Ski Resort VT Vacation Condos
9.6 out of 10, Exceptional, (7 reviews)
The price is AU$289
includes taxes & fees
22 Jan - 23 Jan
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
7.6 out of 10, Good, (39 reviews)
"Clean, comfortable, full kitchen, fast internet, plenty of parking, great location right by the Killington base lodges. Would definitely stay here again."
United States
Brian B.
The price is AU$558
includes taxes & fees
14 Jan - 15 Jan
Mountain view condo with full kitchen and free WiFi
10.0 out of 10, Exceptional, (14 reviews)
"My husband and i really enjoyed our stay at Jack S'bearo! Was a nice, cozy condo for a couple or a small family. Highly recommend!"
United States
Erin
The price is AU$472
includes taxes & fees
14 Jan - 15 Jan
Jack S`Bearo - Slopes, Fireplace, Pool.
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 AU$395
includes taxes & fees
19 Jan - 20 Jan
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
9.4 out of 10, Exceptional, (9 reviews)
"Great property, as advertised."
United States
Chris A.
The price is AU$509
includes taxes & fees
26 Jan - 27 Jan
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
8.2 out of 10, Very good, (35 reviews)
"It was clean and as advertised"
United States
Kiehl H.
The price is AU$509
includes taxes & fees
26 Jan - 27 Jan
Resort condo with balcony & shared seasonal amenities - close to skiing
8.8 out of 10, Excellent, (5 reviews)
"This was perfect for our girls weekend! Great location, spacious & clean. Our host was so responsive & kind- highly recommend staying here when you visit Salem! "
United States
Brianna L.
The price is AU$374
includes taxes & fees
14 Jan - 15 Jan
Vermont Double Queen Suite | 10 min to Killington
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

Find out more about Pittsfield

Everything you need to know about Pittsfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pittsfield holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Pittsfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pittsfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pittsfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsfield holiday rentals we have selected for you start as low as AU$289 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pittsfield rentals

At Expedia, we put the best Pittsfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pittsfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pittsfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pittsfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 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.