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

Pittsfield Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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

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.

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
The price is ￥29,750
￥98,267 total
includes taxes & fees
Sep 8 - Sep 9
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
A house with a large porch, a covered entryway, and a deck.

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.
The price is ￥63,442
￥149,558 total
includes taxes & fees
Sep 8 - Sep 9
Royalbear-AC, Hot Tub, Grill, FirePit, Gameroom
A wooden deck with a covered seating area, a grill, and string lights.

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.
The price is ￥25,783
￥52,503 total
includes taxes & fees
Sep 20 - Sep 21
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
A stone-walled patio with outdoor seating, overlooking a river and a mountainous landscape, decorated with string lights.

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.
The price is ￥86,138
￥140,265 total
includes taxes & fees
Oct 5 - Oct 6
Breathtaking Riverfront Farmhouse w/Mountain Views
A large house with a fire pit and outdoor seating.

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.
The price is ￥25,002
￥74,030 total
includes taxes & fees
Sep 8 - Sep 9
Beautiful 3-bedroom house with AC in charming Bridgewater
A two-story house with a green roof, a covered porch, and a driveway with a parked car.

6. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
The price is ￥18,751
￥36,052 total
includes taxes & fees
Sep 8 - Sep 9
Bridgewater Living - Ski VT Suite
A spacious living room with a stone fireplace, wooden furniture, and large windows.

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.
The price is ￥28,713
￥107,904 total
includes taxes & fees
Sep 8 - Sep 9
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
A white building with a porch, a signboard, and a road with a white fence in the background.

8. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite
Bridgewater
The price is ￥18,751
￥36,227 total
includes taxes & fees
Sep 8 - Sep 9
Bridgewater Living - Ben&Jerry Suite
A cozy living room with a sofa, armchair, and a bookshelf. There is a fireplace and a window providing natural light.

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.
The price is ￥62,035
￥129,333 total
includes taxes & fees
Sep 22 - Sep 23
Authentic farmhouse for those who love cozy, quirky, historical imperfection
A covered porch with a view of a white house and a green lawn.

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.
The price is ￥117,195
￥219,639 total
includes taxes & fees
Sep 10 - Sep 11
150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
A deck with outdoor furniture, a flag, and a view of a forested hill.

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
The price is ￥49,222
￥82,080 total
includes taxes & fees
Sep 17 - Sep 18
Lovely Chalet atop Vermont’s Green Mountains - perfect for a cozy getaway
A red building with a bear logo, a stone pathway, and neatly trimmed bushes.

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.
The price is ￥17,532
￥26,128 total
includes taxes & fees
Sep 8 - Sep 9
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
A wooden cabin interior with a kitchen featuring a stainless steel refrigerator, a stove, and a sink. There are two stools at a bar area, and a ladder is leaning against the wall.

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

Brookside Cabin - Your Peaceful VT Off-Grid Escape
Brookfield
The price is ￥27,502
￥69,305 total
includes taxes & fees
Sep 10 - Sep 11
Brookside Cabin - Your Peaceful VT Off-Grid Escape
A spacious kitchen with a large island, stone walls, wooden beams, and modern appliances.

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.
The price is ￥132,821
￥216,833 total
includes taxes & fees
Sep 12 - Sep 13
NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!

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.
The price is ￥50,459
￥96,395 total
includes taxes & fees
Sep 13 - Sep 14
Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!

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.
The price is ￥82,974
￥177,810 total
includes taxes & fees
Sep 13 - Sep 14
New Luxury Home in Killington with Hot Tub, Sauna and Fireplace
A cabin with a deck and a stone chimney.

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.
The price is ￥57,871
￥176,593 total
includes taxes & fees
Sep 8 - Sep 9
The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
A wooden cabin with multiple balconies and a stone chimney.

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.
The price is ￥32,452
￥91,742 total
includes taxes & fees
Sep 8 - Sep 9
Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
A spacious living area with a dining table, chairs, a sofa, and a large window.

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.
The price is ￥33,627
￥88,851 total
includes taxes & fees
Sep 14 - Sep 15
SunBear- AC, Pool, Game Room, Fireplace, Hiking!

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.
The price is ￥126,571
￥244,025 total
includes taxes & fees
Sep 9 - Sep 10
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.
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

The Jackson

The Jackson

10/10 Excellent
"The inn and the grounds are beautifully maintained. The room was comfortable, and the restaurant on the premises was convenient but also had a great breakfast, well worth purchasing. The location was also great relative to downtown."
Vicki 1-night trip
Posted 3 hours ago
The Jackson

Find out more about Pittsfield

Search for holiday rentals in Pittsfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Pittsfield using one of the methods below:

  • View our selection of featured holiday rentals in Pittsfield
  • Use the map to find apartments and other holiday homes in the Pittsfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pittsfield while they last

Look no further and take a look at our great range of rental properties in Pittsfield!

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.