Pittsfield Holiday Rentals

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Holiday Rentals in Pittsfield

The Getaway 4 Bedroom Home

3.0 star property
Pittsfield
The price is NZ$1,672
includes taxes & fees
14 Nov - 15 Nov
The Getaway 4 Bedroom Home

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

Pittsfield
The price is NZ$1,440
includes taxes & fees
14 Nov - 15 Nov
The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!

Off Grid Glamping Shed with River Access

2.0 star property
Randolph
10.0 out of 10, Exceptional, (1)
The price is NZ$165
includes taxes & fees
14 Nov - 15 Nov
Off Grid Glamping Shed with River Access

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 NZ$763
includes taxes & fees
17 Nov - 18 Nov
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

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 NZ$844
includes taxes & fees
17 Nov - 18 Nov
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Bridgewater
9.4 out of 10, Exceptional, (16)
"It was a great location for what we were looking to do. Great size and we loved the hot tub. Very comfortable. We enjoyed our stay and would come again"
United States
Ashley G.
The price is NZ$867
includes taxes & fees
16 Nov - 17 Nov
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

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 NZ$494
includes taxes & fees
18 Nov - 19 Nov
CozyDen-Location, Fireplace, Ski Off/Shuttle On!

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

Killington Ski Resort VT Vacation Condos

3.5 star property
Killington
The price is NZ$521
includes taxes & fees
18 Nov - 19 Nov
Killington Ski Resort VT Vacation Condos

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 NZ$414
includes taxes & fees
14 Nov - 15 Nov
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A

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 NZ$729
includes taxes & fees
14 Nov - 15 Nov
Dreamy Artist Chalet in Secluded Historic Village

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 traveller
The price is NZ$430
includes taxes & fees
16 Nov - 17 Nov
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

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 NZ$486
includes taxes & fees
18 Nov - 19 Nov
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

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

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 NZ$570
includes taxes & fees
16 Nov - 17 Nov
Luxury Condo Tucked in the Heart of Killington

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 NZ$718
includes taxes & fees
17 Nov - 18 Nov
FirBear- Pool, Gym, Hot tub.

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

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 NZ$431
includes taxes & fees
17 Nov - 18 Nov
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

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 NZ$358
includes taxes & fees
14 Nov - 15 Nov
Doc's Lake house 1st floor, 2 bedroom apartment

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 NZ$546
includes taxes & fees
19 Nov - 20 Nov
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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Find out more about Pittsfield

Everything you need to know about Pittsfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pittsfield holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pittsfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsfield holiday rentals we have selected for you start as low as NZ$165 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pittsfield rentals

At Expedia, we put the best Pittsfield holiday 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 holiday.

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. 

Frequently asked questions

Can I find a holiday rental in Pittsfield?

Yes, there are holiday rentals close to the most popular sights in Pittsfield, or you can select a more secluded option if you're looking for a relaxing stay. Pittsfield is known for its bars and restaurants.

What are some of the best holiday rentals that Pittsfield has to offer?

Killington Mountain Home! HotTub & 5 min to Skiing! by RedAwning: This holiday 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 holiday with 1 hot tub and table football.

How many holiday rentals are there in Pittsfield?

Expedia has 29 holiday 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 holiday rentals like in Pittsfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pittsfield. Holiday rentals offer extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family gatherings.