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

Smart TV, offices

1. 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
$543 nightly
The price is $613
Sep 9 - Sep 10
Total with taxes and fees
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
Exterior

2. Royalbear-AC, Hot Tub, Grill, FirePit, Gameroom

Royalbear-AC, Hot Tub, Grill, FirePit, Gameroom
Killington
10.0 out of 10, Exceptional, (24 reviews)
"Great house and location, and responsive hosts. Loved it, def will stay again."
United States
Max P.
$847 nightly
The price is $957
Sep 7 - Sep 8
Total with taxes and fees
Royalbear-AC, Hot Tub, Grill, FirePit, Gameroom
Terrace/patio

3. 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, (15 reviews)
"That was the most beautiful stay that we’ve had in a long time. Everything was absolutely perfect. We will definitely be back."
United States
Kaity F.
$300 nightly
The price is $336
Sep 20 - Sep 21
Total with taxes and fees
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Terrace/patio

4. Breathtaking Riverfront Farmhouse w/Mountain Views

Breathtaking Riverfront Farmhouse w/Mountain Views
Bridgewater
9.8 out of 10, Exceptional, (10 reviews)
"We loved our stay at this property. Cool, unique layout, lots of space, impressive master bedroom, amazing scenery with the river flowing literally behind the property. Great location in between Woodstock and Killington. Very helpful hosts and easy check in. Would definitely recommend"
United States
Matthew V.
$795 nightly
The price is $898
Oct 5 - Oct 6
Total with taxes and fees
Breathtaking Riverfront Farmhouse w/Mountain Views
Property grounds

5. Beautiful 3-bedroom house with AC in charming Bridgewater

Beautiful 3-bedroom house with AC in charming Bridgewater
Bridgewater
10.0 out of 10, Exceptional, (2 reviews)
"Great house with fun decorations. Comfortable with lots of room; full kitchen with ample dining area. Loved the coffee available and the sound machine in the bedroom- great conveniences! Communication around booking were great with easy check in and check out."
United States
Susan S.
$423 nightly
The price is $474
Sep 7 - Sep 8
Total with taxes and fees
Beautiful 3-bedroom house with AC in charming Bridgewater
Exterior

6. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
$206 nightly
The price is $231
Sep 7 - Sep 8
Total with taxes and fees
Bridgewater Living - Ski VT Suite
TV

7. Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Plymouth
9.8 out of 10, Exceptional, (24 reviews)
"convenient to okemo"
United States
marcus l.
$617 nightly
The price is $691
Sep 7 - Sep 8
Total with taxes and fees
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Property grounds

8. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite
Bridgewater
$207 nightly
The price is $232
Sep 7 - Sep 8
Total with taxes and fees
Bridgewater Living - Ben&Jerry Suite
Smart TV, fireplace, video games, books

9. Authentic farmhouse for those who love cozy, quirky, historical imperfection

Authentic farmhouse for those who love cozy, quirky, historical imperfection
Randolph Center
10.0 out of 10, Exceptional, (6 reviews)
"The rental experience was seemless....communication was great, the property fit our family so easily and the location was easily accessible to many beautiful spots. The home is well equipped and it was a delightful stay!"
United States
Kathy K.
$731 nightly
The price is $819
Sep 29 - Sep 30
Total with taxes and fees
Authentic farmhouse for those who love cozy, quirky, historical imperfection
Terrace/patio

10. 150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!

150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
Bethel
10.0 out of 10, Exceptional, (1 review)
"Light Hill is a beautiful property and the hosts are wonderful. We had a fantastic time there and our kids spent hours catching newts and frogs in the pond, swinging, and running around the yard. We enjoyed sitting on the screened in porch overlooking the mountains and just feeling very relaxed here. We are hoping to come back someday!"
United States
Andrew V.
$1,257 nightly
The price is $1,408
Sep 7 - Sep 8
Total with taxes and fees
150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
Outdoor dining

11. Lovely Chalet atop Vermont’s Green Mountains - perfect for a cozy getaway

Lovely Chalet atop Vermont’s Green Mountains - perfect for a cozy getaway
Woodstock
$469 nightly
The price is $525
Sep 17 - Sep 18
Total with taxes and fees
Lovely Chalet atop Vermont’s Green Mountains - perfect for a cozy getaway
Exterior

12. 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.
$154 nightly
The price is $167
Sep 7 - Sep 8
Total with taxes and fees
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Coffee/tea maker, fridge, oven, stovetop

13. Brookside Cabin - Your Peaceful VT Off-Grid Escape

Brookside Cabin - Your Peaceful VT Off-Grid Escape
Brookfield
$396 nightly
The price is $444
Sep 8 - Sep 9
Total with taxes and fees
Brookside Cabin - Your Peaceful VT Off-Grid Escape
Microwave, oven, stovetop, dishwasher

14. NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!

NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
Killington
10.0 out of 10, Exceptional, (4 reviews)
"Location near gondola was clutch (short 1 min drive). Super clean and layout of cabin was perfect for our group. We had a fair amount of snow and icy weather and our host kept the road and driveway clear."
United States
Jeremy F.
$1,228 nightly
The price is $1,388
Sep 12 - Sep 13
Total with taxes and fees
NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
Smart TV

15. Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!

Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!
Killington
10.0 out of 10, Exceptional, (1 review)
"Beautiful home made for a perfect holiday weekend"
United States
Gregg Z.
$546 nightly
The price is $617
Sep 13 - Sep 14
Total with taxes and fees
Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!
Exterior

16. New Luxury Home in Killington with Hot Tub, Sauna and Fireplace

New Luxury Home in Killington with Hot Tub, Sauna and Fireplace
Killington
10.0 out of 10, Exceptional, (4 reviews)
"We had a fabulous time enjoying this lovely property! The host, Erin, was super responsive and helpful, we will definitely be returning for future visits! "
United States
jeannie g.
$840 nightly
The price is $949
Sep 15 - Sep 16
Total with taxes and fees
New Luxury Home in Killington with Hot Tub, Sauna and Fireplace
Terrace/patio

17. 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.
$979 nightly
The price is $1,107
Sep 9 - Sep 10
Total with taxes and fees
The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
Exterior

18. Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Killington
9.4 out of 10, Exceptional, (58 reviews)
"Great stay. We really loved the ski in ski out feature. Host was responsive with any issues"
United States
Andrea W.
$504 nightly
The price is $569
Sep 9 - Sep 10
Total with taxes and fees
Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Interior

19. SunBear- AC, Pool, Game Room, Fireplace, Hiking!

SunBear- AC, Pool, Game Room, Fireplace, Hiking!
Killington
9.8 out of 10, Exceptional, (31 reviews)
"Very accommodating and helpful hosts"
United States
Sean W.
$503 nightly
The price is $569
Sep 14 - Sep 15
Total with taxes and fees
SunBear- AC, Pool, Game Room, Fireplace, Hiking!
Interior

20. 7 Bedrooms in the Heart of Killington - Game Room, Hot Tub, Easily Sleeps 16

7 Bedrooms in the Heart of Killington - Game Room, Hot Tub, Easily Sleeps 16
Killington
9.6 out of 10, Exceptional, (9 reviews)
"Host was very communicative throughout our stay. Place was as described and plenty big enough for our family."
United States
Dawn L.
$1,382 nightly
The price is $1,562
Sep 9 - Sep 10
Total with taxes and fees
7 Bedrooms in the Heart of Killington - Game Room, Hot Tub, Easily Sleeps 16
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

Hampton Inn Rutland

Hampton Inn Rutland

8/10 Good
"Most of the staff at the front desk needs to work on their people skills big time!!"
Kasey 4-night trip
Posted 4 hours ago
Hampton Inn Rutland

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?

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.