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

Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Pittsfield vacation rentals

Living area

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

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

3. 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.
$478 nightly
The price is $505
Sep 15 - Sep 16
Total with taxes and fees
Gnome Home Mountain Ski Chalet w/Sauna Killington
Interior

4. 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.
$534 nightly
The price is $598
Sep 7 - Sep 8
Total with taxes and fees
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Exterior

5. 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.
$534 nightly
The price is $598
Sep 7 - Sep 8
Total with taxes and fees
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Outdoor dining

6. 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, (14 reviews)
"We had a great time!"
United States
Matthew R.
$400 nightly
The price is $452
Sep 28 - Sep 29
Total with taxes and fees
Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub
Terrace/patio

7. Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging

Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging
Killington
10.0 out of 10, Exceptional, (3 reviews)
"The accommodations exceeded the expectations in all ways.The booking, check in and communication with the hosts we're problem free and I would highly recommend this property and host to everyone seeking a beautiful and stress free get away."
United States
SHEEPDOG 1.
Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging
Living area

8. Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining

Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining
Killington
10.0 out of 10, Exceptional, (3 reviews)
"great rental overall, the unit was well stocked, clean and have everything you need for your stay."
United States
matt d.
Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining
Room

9. DoubleDen- AC, Hot Tub, Fire pit, Grill, Game Room

DoubleDen- AC, Hot Tub, Fire pit, Grill, Game Room
Killington
10.0 out of 10, Exceptional, (26 reviews)
"Ver accommodating the property was amazing. "
United States
Jessica M.
$895 nightly
The price is $1,011
Sep 14 - Sep 15
Total with taxes and fees
DoubleDen- AC, Hot Tub, Fire pit, Grill, Game Room
Living area

10. Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole

Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole
Killington
10.0 out of 10, Exceptional, (6 reviews)
"Such a great spot."
United States
Kathleen G.
$878 nightly
The price is $960
Sep 4 - Sep 5
Total with taxes and fees
Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole
Living area

11. 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
Sep 6 - Sep 7
Total with taxes and fees
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
Property grounds

12. 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
Sep 7 - Sep 8
Total with taxes and fees
CubsCorner - Pool, Sauna, Gym, Close to Mountain!
Terrace/patio

13. Estelle Cottage- Private Sauna, Hot tub, Pool, AC

Estelle Cottage- Private Sauna, Hot tub, Pool, AC
The Woods
10.0 out of 10, Exceptional, (2 reviews)
"Yes!! King beds!! Tall people love king beds and they delivered. This does not diminish the fact that everything was excellent for our stay. From the welcome gifts including some great local coffee and syrup, to the relaxing sauna, the comfortable large living room and bedrooms, and all amenities, we wanted for nothing. Truly a gem on our whole vacation! We looked forward to returning in the late afternoon knowing we had a quiet evening and a good sleep ahead of us. Truly a great place to...
United States
Devin
$619 nightly
The price is $677
Sep 8 - Sep 9
Total with taxes and fees
Estelle Cottage- Private Sauna, Hot tub, Pool, AC
Living area

14. The Big Lebearski- AC, Grill, Fire Pit, Hot tub!

The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
Killington
10.0 out of 10, Exceptional, (21 reviews)
"Great location and excellent hosts "
United States
Peter G.
$582 nightly
The price is $658
Sep 8 - Sep 9
Total with taxes and fees
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
Room

15. 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.
$241 nightly
The price is $272
Sep 7 - Sep 8
Total with taxes and fees
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Living area

16. FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym

FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym
The Woods
10.0 out of 10, Exceptional, (24 reviews)
"Loved the pool, sauna, and steam room. Really nice place, everything we needed. "
United States
Lisa N.
$369 nightly
The price is $417
Sep 7 - Sep 8
Total with taxes and fees
FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym
Interior

17. BearWatch AC Hot Tub, Games, Grill, FirePit, VIEWS

BearWatch AC Hot Tub, Games, Grill, FirePit, VIEWS
Killington
10.0 out of 10, Exceptional, (15 reviews)
"Great property, highly recommend. "
United States
Michael J.
$738 nightly
The price is $834
Sep 15 - Sep 16
Total with taxes and fees
BearWatch AC Hot Tub, Games, Grill, FirePit, VIEWS
Living area

18. 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
Sep 7 - Sep 8
Total with taxes and fees
Rustic Mountain Retreat Just Minutes to Pico & Killington for a Perfect Getaway
Terrace/patio

19. The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.

The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
Killington
10.0 out of 10, Exceptional, (63 reviews)
"Great stay, everything was clean and location was amazing."
United States
John D.
$1,068 nightly
The price is $1,206
Sep 7 - Sep 8
Total with taxes and fees
The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
Property grounds

20. Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around

Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The host was easy to communicate with, gracious and helpful. Amenities were generous and everything was in excellent condition. Really enjoyed the quiet treed setting and the hot tub."
United States
Elizabeth N.
$512 nightly
The price is $573
Sep 9 - Sep 10
Total with taxes and fees
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
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

Sleep Woodstock Motel

Sleep Woodstock Motel

10/10 Excellent
"Newly renovated and the decor was perfect"
Halina 1-night trip
Posted 1 hour ago
Sleep Woodstock Motel

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 $189 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.