Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
Feb 20 - Feb 22
In two months
Apr 3 - Apr 5
In three months
May 1 - May 3
In four months
May 29 - May 31

Our top choices for Pittsfield vacation rentals

Smart TV, offices

NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
North Sherburne
$553 nightly
The price is $620
Feb 10 - Feb 11
Total with taxes and fees
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
TV

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
North Sherburne
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.
$583 nightly
The price is $653
Feb 11 - Feb 12
Total with taxes and fees
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
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, (7 reviews)
"Cabin was spotless and exactly what I expected"
United States
mark g.
$278 nightly
The price is $311
Mar 5 - Mar 6
Total with taxes and fees
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Property grounds

Secluded retreat in the trees

Secluded retreat in the trees
Roxbury
10.0 out of 10, Exceptional, (39 reviews)
"Perfect, quiet location and the host were very responsive! Me and my daughter stayed for a girls getaway for a hiking trip and the location was perfect for the weekend activities. Look forward to staying here in the future. "
United States
Erin M.
$216 nightly
The price is $242
Feb 10 - Feb 11
Total with taxes and fees
Secluded retreat in the trees
1 bedroom, iron/ironing board, travel crib, free WiFi

Cozy Cabin Retreat

Cozy Cabin Retreat
Roxbury
10.0 out of 10, Exceptional, (34 reviews)
"Lovely, quiet & the BEST star gazing!!!"
United States
Jill F.
$190 nightly
The price is $213
Feb 10 - Feb 11
Total with taxes and fees
Cozy Cabin Retreat
Dining

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
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.
$168 nightly
The price is $188
Feb 11 - Feb 12
Total with taxes and fees
Cozy Rutland Retreat
Property grounds

Vermont Suite | 10 Min to Killington & Woodstock

Vermont Suite | 10 Min to Killington & Woodstock
Bridgewater
9.2 out of 10, Wonderful, (7 reviews)
"Overall, a great stay. "
United States
Meghan J.
$196 nightly
The price is $214
Feb 10 - Feb 11
Total with taxes and fees
Vermont Suite | 10 Min to Killington & Woodstock
Property grounds

Cozy Rustic Cabin, NOTE: pipes are frozen. Please don’t book now! Back soon.

Cozy Rustic Cabin, NOTE: pipes are frozen. Please don’t book now! Back soon.
Rutland
9.6 out of 10, Exceptional, (9 reviews)
$171 nightly
The price is $192
Feb 10 - Feb 11
Total with taxes and fees
Cozy Rustic Cabin, NOTE: pipes are frozen. Please don’t book now! Back soon.
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.
$235 nightly
The price is $263
Mar 1 - Mar 2
Total with taxes and fees
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Interior

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Mendon
9.8 out of 10, Exceptional, (11 reviews)
"Great place! Secluded but close to everything. We will definitely stay again."
United States
Patricia Y.
$391 nightly
The price is $438
Feb 10 - Feb 11
Total with taxes and fees
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Aerial view

Mountain Green

Mountain Green
2.0 star property
Killington
7.0 out of 10, Good, (19 reviews)
"Great !"
United States
Raul
$241 nightly
The price is $265
Feb 10 - Feb 11
Total with taxes and fees
Mountain Green
Fridge, microwave, oven, stovetop

Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Comfortable stay, great location. "
United States
Marjana
$346 nightly
The price is $369
Feb 10 - Feb 11
Total with taxes and fees
Luxury Condo Tucked in the Heart of Killington
Indoor pool

Clean & bright condo with mountain views & modern kitchen - walk to lifts

Clean & bright condo with mountain views & modern kitchen - walk to lifts
Killington
7.2 out of 10, Good, (45 reviews)
"Perfect place for a long weekend"
United States
Patrick D.
$221 nightly
The price is $250
Feb 10 - Feb 11
Total with taxes and fees
Clean & bright condo with mountain views & modern kitchen - walk to lifts
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, (71 reviews)
"Great place to stay for a Vermont getaway! "
United States
Jeremy H.
$170 nightly
The price is $190
Feb 10 - Feb 11
Total with taxes and fees
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Fridge, microwave, oven, stovetop

Jack S`Bearo - Slopes, Fireplace, Pool.

Jack S`Bearo - Slopes, Fireplace, Pool.
Killington
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
$273 nightly
The price is $309
Mar 4 - Mar 5
Total with taxes and fees
Jack S`Bearo - Slopes, Fireplace, Pool.
Fridge, microwave, oven, stovetop

Dreamy Artist Chalet in Secluded Historic Village

Dreamy Artist Chalet in Secluded Historic Village
East Warren
9.4 out of 10, Exceptional, (11 reviews)
"Everything was beautiful. But for sure needs new mattress and pillows. "
United States
Jeanette R.
$393 nightly
The price is $440
Feb 10 - Feb 11
Total with taxes and fees
Dreamy Artist Chalet in Secluded Historic Village
Interior

Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.6 out of 10, Exceptional, (40 reviews)
"The place was spacious, but small, which I loved! Plenty of hot water, great communication with owner, plenty of extra chairs and the leaf for the table was fantastic!"
United States
Michael M.
Beautiful home located in the Mad River Valley
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.
$542 nightly
The price is $575
Mar 3 - Mar 4
Total with taxes and fees
Gnome Home Mountain Ski Chalet w/Sauna Killington
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, (35 reviews)
"Great stay!"
United States
Bryann F.
$319 nightly
The price is $361
Mar 2 - Mar 3
Total with taxes and fees
Comfortable mountain gem with pool, mountain views, & indoor parking space
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, (31 reviews)
"beds were comfortable"
United States
Juan T.
$315 nightly
The price is $356
Mar 9 - Mar 10
Total with taxes and fees
Welcoming condo near the slopes with free WiFi and full kitchen
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

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"The staff could not have been more accommodating. From the front desk to the shuttle drivers, to the wait staff in the restaurant, they were all friendly, helpful and pleasant."
Brian 2-night trip
Posted 1 day ago
The Mountain Inn at Killington

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 $190 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?

Spectacular opportunity to enjoy the finest property in Killington Summit: This vacation home rental outside of Pittsfield is located in the mountains and has a patio, a selection of games, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a hot tub.

How many vacation rentals are there in Pittsfield?

Expedia has 29 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.