A lake surrounded by autumn-colored trees and a rocky shoreline.

Pittsfield Vacation Rentals

Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Pittsfield vacation rentals

A spacious living area with a red sectional sofa, a wooden dining table, and a kitchen in the background.

1. 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.
$543 nightly
The price is $613
Aug 25 - Aug 26
Total with taxes and fees
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
A modern living room with a red sectional sofa, a round coffee table, wooden ceiling beams, a kitchen area, and a balcony with a view of trees.

2. 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
$539 nightly
The price is $608
Aug 25 - Aug 26
Total with taxes and fees
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
A living room with a wooden console table, a potted plant, and two clocks. A staircase and a fireplace with a TV are in the background.

3. Ski Home/Arcade Mountain Views Near Killington/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
United States
Kevin M.
$524 nightly
The price is $587
Aug 24 - Aug 25
Total with taxes and fees
Ski Home/Arcade Mountain Views Near Killington/Woodstock

4. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
$524 nightly
The price is $587
Aug 24 - Aug 25
Total with taxes and fees
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
A rustic cabin with a wooden deck, surrounded by dense greenery and a rocky landscape.

5. Gnome Home Mountain Ski Chalet w/Sauna Killington

Gnome Home Mountain Ski Chalet w/Sauna Killington
Stockbridge
10.0 out of 10, Exceptional, (5 reviews)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
$493 nightly
The price is $521
Aug 30 - Aug 31
Total with taxes and fees
Gnome Home Mountain Ski Chalet w/Sauna Killington
A snow-covered residential area with multi-story buildings, a ski slope in the background, and a clear sky.

6. Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (29 reviews)
"The property is under major construction which was not disclosed when booking. The management fee was almost as much as the room rate, clearer description at time of booking would be appreciated."
United States
Keith
$210 nightly
The price is $231
Aug 31 - Sep 1
Total with taxes and fees
Mountain Green
A bedroom with a large bed, a TV mounted on the wall, and a sliding door leading to a bathroom.

7. 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, (16 reviews)
"Great condo and building. Everything in excellent condition. Convenient location."
United States
Joseph S.
$240 nightly
The price is $271
Aug 26 - Aug 27
Total with taxes and fees
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
A living room with a fireplace, a sofa, a coffee table, and a television.

8. 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, (47 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
$336 nightly
The price is $380
Aug 24 - Aug 25
Total with taxes and fees
Resort condo with mountain views, full kitchen, and free WiFi
A wooden deck with a hot tub, a table, and chairs.

9. Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub

Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub
North Sherburne
8.2 out of 10, Very Good, (13 reviews)
"We had a great time!"
United States
Matthew R.
$399 nightly
The price is $450
Aug 24 - Aug 25
Total with taxes and fees
Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub
A living room with a sofa, a dining table with chairs, a kitchen area with wooden cabinets, and a bar.

10. Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
Killington
9.8 out of 10, Exceptional, (13 reviews)
"We had such a great time staying here. It was clean, cozy and so convenient to walk right out the door to the slopes! "
United States
Susanne B.
$308 nightly
The price is $348
Aug 27 - Aug 28
Total with taxes and fees
Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
A cozy living room with a brick fireplace, two sofas, a coffee table, and a TV mounted on the wall.

11. Killington condo 5 min to killington resort

Killington condo 5 min to killington resort
Killington
9.4 out of 10, Exceptional, (9 reviews)
"Great location!!"
United States
Nicholas C.
$301 nightly
The price is $340
Aug 30 - Aug 31
Total with taxes and fees
Killington condo 5 min to killington resort
A cozy living room with a sectional sofa, a coffee table, and a fireplace.

12. Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
$639 nightly
The price is $702
Aug 24 - Aug 25
Total with taxes and fees
Breakaway House by Killington Vacation Rentals
A spacious living room with leather sofas, a wooden ceiling, large windows, and a kitchen area.

13. Rustic Mountain Retreat Just Minutes to Pico & Killington for a Perfect Getaway

Rustic Mountain Retreat Just Minutes to Pico & Killington for a Perfect Getaway
Mendon
$486 nightly
The price is $544
Aug 24 - Aug 25
Total with taxes and fees
Rustic Mountain Retreat Just Minutes to Pico & Killington for a Perfect Getaway
A red building with a bear logo, a stone pathway, and neatly trimmed bushes.

14. Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102

Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Killington
8.8 out of 10, Excellent, (8 reviews)
"Great room, plenty of amenities, close to restaurants and mountains"
United States
Daniel T.
$145 nightly
The price is $157
Aug 24 - Aug 25
Total with taxes and fees
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
A snow-covered outdoor area with a large arch structure, rocks, and a building in the background.

15. CubsCorner - Pool, Sauna, Gym, Close to Mountain!

CubsCorner - Pool, Sauna, Gym, Close to Mountain!
Killington
10.0 out of 10, Exceptional, (6 reviews)
"Great location with access to both Pico and Killington Mountains!"
United States
Olaf G.
$417 nightly
The price is $460
Aug 24 - Aug 25
Total with taxes and fees
CubsCorner - Pool, Sauna, Gym, Close to Mountain!
A modern kitchen with a central island, stainless steel appliances, and wooden cabinets.

16. Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
Killington
9.6 out of 10, Exceptional, (71 reviews)
"Cozy space close to the mountain. Host was very responsive and check in and check out was easy. "
United States
Spencer P.
$301 nightly
The price is $340
Aug 26 - Aug 27
Total with taxes and fees
Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

17. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (16 reviews)
"The location was perfect, the property is very well maintained and comfortable. I would highly recommend this place!"
United States
Valerie
$177 nightly
The price is $180
Aug 24 - Aug 25
Total with taxes and fees
Cozy Rutland Retreat
A rustic interior with a stone fireplace, wooden beams, leather furniture, and a balcony with a view.

18. Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Killington
10.0 out of 10, Exceptional, (21 reviews)
"Cannon was cozy, clean, and as described. "
United States
Addams S.
$406 nightly
The price is $459
Aug 26 - Aug 27
Total with taxes and fees
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
A rustic cabin surrounded by autumn foliage.

19. Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
10.0 out of 10, Exceptional, (26 reviews)
"We had a great time! "
United States
Allie T.
Beautiful home located in the Mad River Valley
A cozy living room with a stone fireplace, a sofa set, and a dining table.

20. Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna

Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
The Woods
10.0 out of 10, Exceptional, (7 reviews)
"Great location and a great place. Felt right at home"
United States
Tyler B.
$608 nightly
The price is $665
Aug 24 - Aug 25
Total with taxes and fees
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
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

North Star Lodge and Resort

North Star Lodge and Resort

10/10 Excellent
"Would visit again great place to stay"
Corey 2-night trip
Posted 2 hours ago
North Star Lodge and Resort

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 $197 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 3 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 28 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.