Pittsfield Holiday Rentals

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Holiday Rentals in Pittsfield

Holiday Home in North Sherburne

10.0 out of 10, Exceptional, (1)
"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.
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Holiday Home in Pittsfield

3.0 star property
The Getaway 4 Bedroom Home

Holiday Home in Pittsfield

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

Cabin in Sharon

10.0 out of 10, Exceptional, (3)
"Very welcoming, awesome weekend getaway."
United States
Zachary B.
The price is AU$404
includes taxes & fees
2 Dec - 3 Dec
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Apartment in Bridgewater

9.2 out of 10, Wonderful, (7)
"Close to Woodstock and market. Easy check in. Very quiet. Kurig, no cups for coffee."
United States
Nancy
The price is AU$300
includes taxes & fees
1 Dec - 2 Dec
Ben & Jerry Suite | Skiing | Hiking | Biking

Cabin in Roxbury

10.0 out of 10, Exceptional, (36)
"Absolutely beautiful! So pleased with everything about our stay!"
United States
Gwen B.
The price is AU$363
includes taxes & fees
10 Dec - 11 Dec
Secluded retreat in the trees

Holiday Home in Tunbridge

9.8 out of 10, Exceptional, (42)
"The accommodations were great with plenty of room. We all wanted to lay on the living room couches because they were so comfortable! The property was nice and peaceful with lots of flowers, bushes and trees to observe."
United States
Karen P.
The price is AU$732
includes taxes & fees
1 Dec - 2 Dec
Spacious country home, beautiful sunsets, 40 acres

Condo in Killington

3.5 star property
The price is AU$521
includes taxes & fees
1 Dec - 2 Dec
The Suites at Killington Center

Condo in Killington

3.5 star property
The price is AU$685
includes taxes & fees
1 Dec - 2 Dec
Mountain Green Resort by Killington VR - 1 Bedrooms

Holiday Home in Bridgewater

9.6 out of 10, Exceptional, (17)
"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "
United States
Gerri B.
The price is AU$835
includes taxes & fees
1 Dec - 2 Dec
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Condo in Killington

9.4 out of 10, Exceptional, (9)
"Great location and clean property"
United States
KEVIN C.
The price is AU$351
includes taxes & fees
1 Dec - 2 Dec
Killington Blue Studio: Sleeps 4, Close to Mtn 123

Condo in Killington

9.6 out of 10, Exceptional, (4)
"The place was clean and easy to get to. "
United States
Sarah Z.
The price is AU$377
includes taxes & fees
1 Dec - 2 Dec
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

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

Cabin in Killington

2.0 star property
10.0 out of 10, Exceptional, (11)
"The cabin was cozy. It was set up nicely and had all the necessities we needed."
United States
Philip
The price is AU$752
includes taxes & fees
1 Dec - 2 Dec
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Apartment in Killington

10.0 out of 10, Exceptional, (11)
"My husband and i really enjoyed our stay at Jack S'bearo! Was a nice, cozy condo for a couple or a small family. Highly recommend!"
United States
Erin
The price is AU$421
includes taxes & fees
30 Nov - 1 Dec
Jack S`Bearo - Slopes, Fireplace, Pool.

Cottage in Mendon

2.0 star property
9.8 out of 10, Exceptional, (11)
"Very clean, and just the perfect getaway. Private and quaint, but close enough to amenities. A very pleasant stay indeed."
United States
Linda B.
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

Condo in Killington

9.6 out of 10, Exceptional, (5)
"My friends and I enjoyed it solid spot for a skiing weekend"
United States
Matt M.
The price is AU$452
includes taxes & fees
1 Dec - 2 Dec
Alpine Oasis Studio at Mountain Green Resort Killington: Shuttle, Pool, Hot Tub, Gym, Deals!

Condo in Killington

9.4 out of 10, Exceptional, (9)
"Great property, as advertised."
United States
Chris A.
The price is AU$410
includes taxes & fees
30 Nov - 1 Dec
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

Condo in Killington

10.0 out of 10, Exceptional, (22)
"Really enjoyed our time there. It's a simple and straightforward apartment. Easy to get to, and a really nice location."
United States
Matthew G.
The price is AU$445
includes taxes & fees
2 Dec - 3 Dec
CozyCub- Location, Fireplace, Ski Off/Shuttle On!

Holiday Home in Warren

9.8 out of 10, Exceptional, (39)
"We had a great time staying at this house during our Sugarbush skiing trip this February. The place is easy to access and is close to the ski resort. The house had everything we needed for a comfortable stay. I highly recommend this rental."
United States
Dmitriy K.
Beautiful home located in the Mad River Valley
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

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 favourite 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 depend 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 AU$235 per night. Entering your travel dates in the search wizard might find you 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?

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.: This holiday home rental outside Pittsfield is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.