Pittsfield Vacation Rentals

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Check prices for these dates

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Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
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Mar 6 - Mar 8

Vacation Rentals in Pittsfield

House, 4 Bedrooms | Exterior
The Getaway 4 Bedroom Home

The Getaway 4 Bedroom Home

3.0 star property
Pittsfield
The price is ￥62,774
￥145,694 total
includes taxes & fees
Nov 14 - Nov 15
The Getaway 4 Bedroom Home
Exterior
The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!

The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!

Pittsfield
The price is ￥51,054
￥125,971 total
includes taxes & fees
Nov 14 - Nov 15
The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!
Property grounds
Off Grid Glamping Shed with River Access

Off Grid Glamping Shed with River Access

2.0 star property
Randolph
10.0 out of 10, Exceptional, (1)
The price is ￥9,013
￥14,410 total
includes taxes & fees
Nov 14 - Nov 15
Off Grid Glamping Shed with River Access
Fridge, microwave, oven, stovetop
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

2.0 star property
Mendon
9.8 out of 10, Exceptional, (11)
"Nice time, great location"
United States
Matthew K.
The price is ￥21,014
￥66,469 total
includes taxes & fees
Nov 17 - Nov 18
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Exterior
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

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

2.0 star property
Killington
10.0 out of 10, Exceptional, (11)
"The Wobbly Cabin is absolutely charming. The decor is tasteful but unique. The kitchen is well stocked and it is clean! I’d also say the beds are great and the linens high quality. If it’s available and big enough for your group definitely book it!"
United States
Nicole E.
The price is ￥22,200
￥73,519 total
includes taxes & fees
Nov 17 - Nov 18
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Fridge, microwave, oven, stovetop
CozyDen-Location, Fireplace, Ski Off/Shuttle On!

CozyDen-Location, Fireplace, Ski Off/Shuttle On!

Killington
10.0 out of 10, Exceptional, (1)
"Very quiet and private feeling even though it is in a condo like setting. Very clean, and had all the conveniences we needed (A/C, coffee maker, full kitchen appliances). And so kind and personal to leave some souvenirs of the area. We felt very comfortable when every we finished our day of sightseeing to come back to our home away from home. "
United States
denise k.
The price is ￥13,311
￥43,069 total
includes taxes & fees
Nov 17 - Nov 18
CozyDen-Location, Fireplace, Ski Off/Shuttle On!
Indoor pool, a heated pool
Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access

Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access

2.0 star property
The Woods
10.0 out of 10, Exceptional, (3)
"We headed up to Killington for some fun spring skiing with the fam and the place was great - spacious, well appointed, and comfortable. Would definitely stay again."
United States
Ryan T.
The price is ￥21,522
￥69,755 total
includes taxes & fees
Nov 17 - Nov 18
Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access
Exterior
Killington Ski Resort VT Vacation Condos

Killington Ski Resort VT Vacation Condos

3.5 star property
Killington
The price is ￥18,310
￥45,417 total
includes taxes & fees
Nov 18 - Nov 19
Killington Ski Resort VT Vacation Condos
Exterior
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A

Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A

Killington
9.2 out of 10, Wonderful, (5)
"I don’t think I’ve ever had such wonderful service checking in and caring for our needs. Amazing response time and outstanding stay. Thank you."
United States
Margaret L.
The price is ￥12,032
￥36,073 total
includes taxes & fees
Nov 16 - Nov 17
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A
Fridge, microwave, oven, stovetop
Dreamy Artist Chalet in Secluded Historic Village

Dreamy Artist Chalet in Secluded Historic Village

East Warren
9.2 out of 10, Wonderful, (10)
"My friend and I came to ride horses for two days at the Icelandic Horse Farm in Fayston, and we knew we wanted a comfortable place nearby for the night in between. The Chalet was in the perfect location between places to eat (we had pizza at the Blue Stone) and the stable. And it is LOVELY inside, beautifully furnished and stocked with everything you need, Highly recommend!"
United States
Gail N.
The price is ￥31,429
￥63,270 total
includes taxes & fees
Nov 17 - Nov 18
Dreamy Artist Chalet in Secluded Historic Village
Fridge, microwave, dishwasher, coffee/tea maker
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, (63)
"Comfortable condo in convenient location near Ramshead. Access to the newly renovated health spa: indoor pool, sauna and hot tub a real bonus. Great place for a few days skiing."
United States
Anonymous traveler
The price is ￥13,727
￥37,446 total
includes taxes & fees
Nov 17 - Nov 18
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
Property grounds
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, (2)
"Cabin was spotless and exactly what I expected"
United States
mark g.
The price is ￥17,409
￥41,584 total
includes taxes & fees
Dec 2 - Dec 3
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Terrace/patio
CozyCub- Location, Fireplace, Ski Off/Shuttle On!

CozyCub- Location, Fireplace, Ski Off/Shuttle On!

Killington
10.0 out of 10, Exceptional, (22)
"Great place to stay and close to the mountain!"
United States
Sam S.
The price is ￥12,479
￥43,000 total
includes taxes & fees
Nov 17 - Nov 18
CozyCub- Location, Fireplace, Ski Off/Shuttle On!
Fridge, microwave, oven, stovetop
Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington

Killington
8.0 out of 10, Very Good, (1)
"The condo was in a beautiful location but was rather isolated from grocery and dining options. Our host was good at communicating however we received a message about the fireplace not being available to us a day before we came and we got there in the dark with no lights on. The condo itself could not really be called "luxury" as it was dated and lacked some basics like soap in the bathroom, a towel hook in the 1/2 bath, kleenex, cracked dishes, etc. Liked that it was near a waterfall and hiking...
United States
Dean
The price is ￥18,380
￥49,910 total
includes taxes & fees
Nov 16 - Nov 17
Luxury Condo Tucked in the Heart of Killington
Indoor pool, a heated pool
FirBear- Pool, Gym, Hot tub.

FirBear- Pool, Gym, Hot tub.

The Woods
10.0 out of 10, Exceptional, (22)
"Everything was exactly as pictured and the hosts of the property went above and beyond with their hospitality "
United States
John
The price is ￥17,803
￥62,596 total
includes taxes & fees
Nov 17 - Nov 18
FirBear- Pool, Gym, Hot tub.
Property grounds
Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley

Warren
9.8 out of 10, Exceptional, (39)
"Great location. Walk to the falls!"
United States
sheri n.
Beautiful home located in the Mad River Valley
Interior
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)
"The place was clean and easy to get to. "
United States
Sarah Z.
The price is ￥11,693
￥37,515 total
includes taxes & fees
Nov 17 - Nov 18
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
Exterior
Doc's Lake house 1st floor, 2 bedroom apartment

Doc's Lake house 1st floor, 2 bedroom apartment

Salisbury
10.0 out of 10, Exceptional, (71)
"Doc’s Lake House is on a beautiful and quiet lake. My family and I regret not staying longer! It is well-stocked with anything you might need (coffee, spices, breakfast items, etc.), which was lovely! Two separate fire pits and water crafts were available for entertainment. The host met us when we arrived and showed us around. He’s very nice and fun to talk with! It was such a wonderful stay! "
United States
Jennifer T.
The price is ￥20,798
￥31,231 total
includes taxes & fees
Nov 14 - Nov 15
Doc's Lake house 1st floor, 2 bedroom apartment
Microwave, oven, stovetop, dishwasher
Killington 2 Story - Escape 2BR/2BA, Sleeps 6, Family & Friends Retreat w/ WiFi

Killington 2 Story - Escape 2BR/2BA, Sleeps 6, Family & Friends Retreat w/ WiFi

2.0 star property
Killington
2.0 out of 10, (1)
The price is ￥13,750
￥47,569 total
includes taxes & fees
Nov 19 - Nov 20
Killington 2 Story - Escape 2BR/2BA, Sleeps 6, Family & Friends Retreat w/ WiFi
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

10/10 Excellent
"Loved the whole hotel staff was great and very helpful and it was very clean!!!"
Joseph 1-night trip
Posted 1 day ago
Hampton Inn Rutland

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:

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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 Mountain Home! HotTub & 5 min to Skiing! by RedAwning: This vacation home rental outside of Pittsfield is located near skiing and has a fireplace, a patio, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and an oven. You can relax into your vacation with a hot tub and foosball.

How many vacation rentals are there in Pittsfield?

Expedia has 29 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.