Holiday Rentals in Pittsfield

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Our top choices for Pittsfield holiday rentals

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, (8 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
The price is €241
includes taxes & fees
19 Apr - 20 Apr
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Stetson Hollow Cabin by Stetson Brook

Stetson Hollow Cabin by Stetson Brook
Warren
9.8 out of 10, Exceptional, (167 reviews)
"Highly recommend. It was the coziest cabin and in great location. We loved having a fire each night after skiing. Perfect pet friendly lodging. "
United States
Leah V.
The price is €375
includes taxes & fees
17 Apr - 18 Apr
Stetson Hollow Cabin by Stetson Brook

Secluded retreat in the trees

Secluded retreat in the trees
Roxbury
10.0 out of 10, Exceptional, (41 reviews)
"We had a great time staying in this house. For our family, it was comfortable, clean and bright and had everything we needed. "
United States
David R.
The price is €204
includes taxes & fees
23 Apr - 24 Apr
Secluded retreat in the trees

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, (74 reviews)
"Great place to stay for a Vermont getaway! "
United States
Jeremy H.
The price is €156
includes taxes & fees
28 Apr - 29 Apr
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

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 €207
includes taxes & fees
19 Apr - 20 Apr
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

Dreamy Artist Chalet in Secluded Historic Village

Dreamy Artist Chalet in Secluded Historic Village
East Warren
9.6 out of 10, Exceptional, (16 reviews)
"Receptive. Clean. If coming in winter/ mud, know that there is zero chance you'll make it unless you have real chains or 4wd. Nice place. "
United States
Jessica S.
The price is €350
includes taxes & fees
20 Apr - 21 Apr
Dreamy Artist Chalet in Secluded Historic Village

Vermont Double Queen Suite | 10 Mins to Killington

Vermont Double Queen Suite | 10 Mins to Killington
Bridgewater
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 €166
includes taxes & fees
19 Apr - 20 Apr
Vermont Double Queen Suite | 10 Mins to Killington

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (7 reviews)
"Very nice place to stay in Rutland."
United States
Dave M.
The price is €162
includes taxes & fees
21 Apr - 22 Apr
Cozy Rutland Retreat

Adorable cabin with screened porch and private fire pit

Adorable cabin with screened porch and private fire pit
Ripton
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful place to stay tucked away in the woods. The owners are extremely thoughtful and personable. Can’t wait to go back. "
United States
Sorin
The price is €294
includes taxes & fees
30 Apr - 1 May
Adorable cabin with screened porch and private fire pit

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 €418
includes taxes & fees
20 Apr - 21 Apr
Gnome Home Mountain Ski Chalet w/Sauna Killington

Resort condo with mountain views, full kitchen, and free WiFi

Resort condo with mountain views, full kitchen, and free WiFi
Killington
8.8 out of 10, Excellent, (46 reviews)
"Very close to Killington and in the shuttle route."
United States
Craig C.
The price is €290
includes taxes & fees
20 Apr - 21 Apr
Resort condo with mountain views, full kitchen, and free WiFi

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Killington
10.0 out of 10, Exceptional, (14 reviews)
"Host was very responsive and the home was great! "
United States
Rebecca B.
The price is €232
includes taxes & fees
19 Apr - 20 Apr
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Comfortable mountain gem with pool, mountain views, & indoor parking space

Comfortable mountain gem with pool, mountain views, & indoor parking space
Killington
8.4 out of 10, Very good, (36 reviews)
"Property was just as advertised. Shuttle to the mountain is only a short 2-3 ride. The spa area was amazing. "
United States
Quinten M.
The price is €238
includes taxes & fees
19 Apr - 20 Apr
Comfortable mountain gem with pool, mountain views, & indoor parking space

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
9.0 out of 10, Wonderful, (15 reviews)
"The apartment was very comfortable, including a very convenient bathroom. There was everything we needed. Though the apartment did not look like the photo on the internet site. There was no street number on the building which made it difficult to find it. "
United States
lilya l.
The price is €211
includes taxes & fees
17 Apr - 18 Apr
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

Feel the real VT! Ski Killington and a foodie’s delight!

Feel the real VT! Ski Killington and a foodie’s delight!
Proctor
10.0 out of 10, Exceptional, (1 review)
"Clean and comfortable home. Plenty of space for our family! Great quiet neighborhood made it easy to relax on our trip."
United States
Rebecca
Feel the real VT! Ski Killington and a foodie’s delight!

Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest

Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
Ripton
9.4 out of 10, Exceptional, (12 reviews)
"Our group booked this place for a ski trip to sugarbush. A remote area, but the cabin was very cool and our host were the best. The warm cinnamon twists in the morning were a big hit and the hot tub was perfect after a day of skiing. Would definitely look into booking this in the summer/fall. "
United States
John H.
The price is €294
includes taxes & fees
19 Apr - 20 Apr
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest

Welcoming condo near the slopes with free WiFi and full kitchen

Welcoming condo near the slopes with free WiFi and full kitchen
Killington
7.4 out of 10, Good, (32 reviews)
"Great location."
United States
Dustin S.
The price is €247
includes taxes & fees
17 Apr - 18 Apr
Welcoming condo near the slopes with free WiFi and full kitchen

Resort condo with balcony & shared seasonal amenities - close to skiing

Resort condo with balcony & shared seasonal amenities - close to skiing
Killington
8.2 out of 10, Very good, (35 reviews)
"It was clean and as advertised"
United States
Kiehl H.
The price is €241
includes taxes & fees
19 Apr - 20 Apr
Resort condo with balcony & shared seasonal amenities - close to skiing

Charming and meticulously cleaned cabin with panoramic view of the Green Mtns

Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
Ripton
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful place. Lots to do around the cabin and in the area. The hosts are very helpful. The cabin has everything you could want for a great stay. "
United States
Susan
The price is €294
includes taxes & fees
22 Apr - 23 Apr
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns

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, (72 reviews)
"Amazing stay! Great location, comfortable,had everything we needed. Would stay again."
United States
George
The price is €247
includes taxes & fees
18 Apr - 19 Apr
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
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, apart-hotels, 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 favorite 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 depends 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 €204 per night. Entering your travel dates in the search wizard you might find 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 area home - 4-seasons, hot tub and A/C: This highly rated holiday home rental in 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 5 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 32 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.