Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Pittsfield vacation rentals

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.
The price is ￥26,315
￥93,627 total
includes taxes & fees
Mar 3 - Mar 4
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
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
The price is ￥46,141
￥116,846 total
includes taxes & fees
Mar 9 - Mar 10
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
Outdoor dining

Glamping hut with WiFi in Ripton, biking, hiking, skiing

Glamping hut with WiFi in Ripton, biking, hiking, skiing
Ripton
10.0 out of 10, Exceptional, (3 reviews)
"Super cute and cozy! It was perfect."
United States
Sarah D.
The price is ￥13,888
￥26,041 total
includes taxes & fees
Mar 3 - Mar 4
Glamping hut with WiFi in Ripton, biking, hiking, skiing
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)
"Very welcoming, awesome weekend getaway."
United States
Zachary B.
The price is ￥20,755
￥46,316 total
includes taxes & fees
Mar 4 - Mar 5
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Property grounds

Vermont Double Queen Suite | 10 Mins to Killington

Vermont Double Queen Suite | 10 Mins to Killington
Bridgewater
8.8 out of 10, Excellent, (5 reviews)
"This was perfect for our girls weekend! Great location, spacious & clean. Our host was so responsive & kind- highly recommend staying here when you visit Salem! "
United States
Brianna L.
The price is ￥15,293
￥33,796 total
includes taxes & fees
Mar 3 - Mar 4
Vermont Double Queen Suite | 10 Mins to Killington
Aerial view

The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is ￥21,192
￥57,642 total
includes taxes & fees
Mar 4 - Mar 5
The Suites at Killington Center
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, (36 reviews)
"Great stay!"
United States
Bryann F.
The price is ￥13,420
￥48,297 total
includes taxes & fees
Mar 4 - Mar 5
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.
The price is ￥14,201
￥47,898 total
includes taxes & fees
Mar 3 - Mar 4
Welcoming condo near the slopes with free WiFi and full kitchen
1 bedroom, iron/ironing board, travel crib, free WiFi

Cozy Cabin Retreat

Cozy Cabin Retreat
Roxbury
10.0 out of 10, Exceptional, (35 reviews)
"Lovely, quiet & the BEST star gazing!!!"
United States
Jill F.
The price is ￥18,398
￥33,365 total
includes taxes & fees
Mar 8 - Mar 9
Cozy Cabin Retreat
TV

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
Killington
9.4 out of 10, Exceptional, (71 reviews)
"Great little condo, near everything and 2 min drive to K1 Lodge. "
United States
zina r.
The price is ￥20,926
￥47,099 total
includes taxes & fees
Mar 3 - Mar 4
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
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.
The price is ￥19,506
￥42,995 total
includes taxes & fees
Mar 4 - Mar 5
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Fireplace, books

Stetson Hollow Cabin by Stetson Brook

Stetson Hollow Cabin by Stetson Brook
Warren
9.8 out of 10, Exceptional, (162 reviews)
"The cabin location was ideal for us , very convenient to outings and very cozy in a gorgeous setting . "
United States
judy c.
The price is ￥33,707
￥69,211 total
includes taxes & fees
Mar 4 - Mar 5
Stetson Hollow Cabin by Stetson Brook
1 bedroom, desk, iron/ironing board, free WiFi

Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
Killington
9.6 out of 10, Exceptional, (4 reviews)
"The place was clean and easy to get to. "
United States
Sarah Z.
The price is ￥20,007
￥51,673 total
includes taxes & fees
Mar 3 - Mar 4
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
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, (73 reviews)
"Great place to stay for a Vermont getaway! "
United States
Jeremy H.
The price is ￥20,287
￥31,460 total
includes taxes & fees
Mar 4 - Mar 5
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
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, (11 reviews)
"Absolutely adored our stay! The cabin was cozy and had everything we could need and the hot tub was a huge plus after a long day of snowboarding. Would definitely come back!"
United States
Erin M.
The price is ￥23,408
￥30,062 total
includes taxes & fees
Mar 11 - Mar 12
Cozy Rustic Cabin, NOTE: pipes are frozen. Please don’t book now! Back soon.
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
7.0 out of 10, Good, (46 reviews)
"Perfect place for a long weekend"
United States
Patrick D.
The price is ￥11,392
￥40,094 total
includes taxes & fees
Mar 11 - Mar 12
Clean & bright condo with mountain views & modern kitchen - walk to lifts
Exterior

The Cozy Cubbie: Charming Studio in Killington. Pool. Bus. Discounted Ski Rentals.

The Cozy Cubbie: Charming Studio in Killington. Pool. Bus. Discounted Ski Rentals.
Killington
9.0 out of 10, Wonderful, (6 reviews)
"We did a quick ski getaway, great place, and close to the mountain!"
United States
Al Z.
The price is ￥12,437
￥40,852 total
includes taxes & fees
Mar 3 - Mar 4
The Cozy Cubbie: Charming Studio in Killington. Pool. Bus. Discounted Ski Rentals.
Living area

Killington condo 5 min to killington resort

Killington condo 5 min to killington resort
Killington
9.4 out of 10, Exceptional, (9 reviews)
"We loved staying here. It was comfortable, had everything we needed. 100% would stay here again!"
United States
Vanessa O.
The price is ￥23,876
￥60,836 total
includes taxes & fees
Mar 4 - Mar 5
Killington condo 5 min to killington resort
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.
The price is ￥21,268
￥67,005 total
includes taxes & fees
Mar 3 - Mar 4
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
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
The price is ￥25,093
￥58,388 total
includes taxes & fees
Mar 24 - Mar 25
Luxury Condo Tucked in the Heart of Killington
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

On The River Inn

On The River Inn

10/10 Excellent
"Friendly and helpful staff "
susan 2-night trip
Posted 14 hours ago
On The River Inn

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
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  • 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?

Roundabout Ridge: This vacation home rental outside of Pittsfield is located in the mountains and has a fireplace, a patio, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

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. Pittsfield Town Hall and Roger Clark Memorial Central Library 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.