Pittsfield Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Pittsfield vacation rentals

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!
Sharon
10.0 out of 10, Exceptional, (8 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
$260 nightly
The price is $291
Apr 19 - Apr 20
Total with taxes and fees
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Fireplace, books

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.
$390 nightly
The price is $437
Apr 17 - Apr 18
Total with taxes and fees
Stetson Hollow Cabin by Stetson Brook
Property grounds

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.
$211 nightly
The price is $236
Apr 23 - Apr 24
Total with taxes and fees
Secluded retreat in the trees
Fridge, microwave, oven, stovetop

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.
$160 nightly
The price is $179
Apr 22 - Apr 23
Total with taxes and fees
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
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
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.
$205 nightly
The price is $230
Apr 19 - Apr 20
Total with taxes and fees
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Fridge, microwave, oven, stovetop

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.
$365 nightly
The price is $409
Apr 18 - Apr 19
Total with taxes and fees
Dreamy Artist Chalet in Secluded Historic Village
Property grounds

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.
$178 nightly
The price is $195
Apr 19 - Apr 20
Total with taxes and fees
Vermont Double Queen Suite | 10 Mins to Killington
Dining

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.
$168 nightly
The price is $188
Apr 19 - Apr 20
Total with taxes and fees
Cozy Rutland Retreat
Exterior

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
$316 nightly
The price is $345
Apr 19 - Apr 20
Total with taxes and fees
Adorable cabin with screened porch and private fire pit
Property grounds

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.
$467 nightly
The price is $493
Apr 20 - Apr 21
Total with taxes and fees
Gnome Home Mountain Ski Chalet w/Sauna Killington
Indoor pool

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.
$308 nightly
The price is $348
Apr 20 - Apr 21
Total with taxes and fees
Resort condo with mountain views, full kitchen, and free WiFi
Fridge, microwave, oven, stovetop

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.
$241 nightly
The price is $272
Apr 19 - Apr 20
Total with taxes and fees
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Property grounds

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.
$246 nightly
The price is $278
Apr 17 - Apr 18
Total with taxes and fees
Comfortable mountain gem with pool, mountain views, & indoor parking space
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
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.
$220 nightly
The price is $249
Apr 17 - Apr 18
Total with taxes and fees
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Fridge, microwave, oven, stovetop

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
$530 nightly
The price is $560
May 11 - May 12
Total with taxes and fees
Feel the real VT! Ski Killington and a foodie’s delight!
Interior

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.
$316 nightly
The price is $345
Apr 19 - Apr 20
Total with taxes and fees
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
Indoor pool

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.
$257 nightly
The price is $290
Apr 17 - Apr 18
Total with taxes and fees
Welcoming condo near the slopes with free WiFi and full kitchen
TV, fireplace, DVD player, books

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.
$253 nightly
The price is $286
Apr 20 - Apr 21
Total with taxes and fees
Resort condo with balcony & shared seasonal amenities - close to skiing
Smart TV, fireplace, DVD player, books

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
$316 nightly
The price is $345
Apr 19 - Apr 20
Total with taxes and fees
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
TV

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
$256 nightly
The price is $289
Apr 18 - Apr 19
Total with taxes and fees
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

On The River Inn

On The River Inn

6/10 Okay
"Night staff was very very nice. Comfortable bed and clean room. TV didn't work unfortunately."
Megan 1-night trip
Posted 3 hours ago
On The River Inn

Find out more about Pittsfield

Everything you need to know about Pittsfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pittsfield vacation 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 low season months. For more hustle and bustle, you may prefer to visit Pittsfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $233 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pittsfield rentals

At Expedia, we put the best Pittsfield vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Pittsfield?

Yes, there are vacation rentals close to popular sights in Pittsfield, or you can choose a more remote option if you're looking for relaxation. Pittsfield is known for its bars and restaurants.

What are some of the best vacation rentals that Pittsfield has to offer?

Killington area home - 4-seasons, hot tub and A/C: This highly rated vacation home rental in Pittsfield is located in the mountains and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Pittsfield?

Expedia has 32 vacation 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 vacation rentals like in Pittsfield?

Vacation rentals are private properties you can reserve for a few days or a quick weekend in Pittsfield. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for a small group gathering.