Pittsfield Holiday Rentals from €138: Search Short-Term Rentals

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

Killington Farmhouse-Mountain Biking, Golf, Hiking : This holiday home rental outside of Pittsfield is located in the mountains, and has a patio, a garden and air conditioning 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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Holiday Rentals in Pittsfield

Cozy living room with a fireplace, leather armchair, and dining table for two.

"Was not listed that soaps and toilet paper is not included. Just would’ve preferred that be out in the listing "

Escape to a secluded cabin surrounded by dense forest, featuring a spacious deck and cozy outdoor seating area.

"We had the most amazing week from check in to check out! We cant wait to come back."

Situated in a serene evergreen forest, this cabin features a symmetrical design with a central chimney and large windows.

"very clean and easy to access close to mountain"

Relax by the rectangular pool surrounded by a paved deck and shaded seating area.

"The condo was very cozy for a family of four and suited us perfectly. Beds were comfortable and condo was clean. "

includes taxes & fees

11 Aug - 12 Aug

Cozy retreat with a large bed, bedside table, and window with a checkered valance.

"There were dead bugs in the bathroom sink and bath, but it's fairly easy to clean them. Everything else in the room is great!"

includes taxes & fees

11 Aug - 12 Aug

Relax by the serene pool surrounded by a paved deck and a covered seating area.

"Convenient for skiing and visiting the greater VT area. Unit has what you need for your stay."

Cozy cabin interior with a high ceiling and exposed beams, featuring a seating area with a sofa and armchairs, bookshelf, and spiral staircase.

"Our stay at the Vermont Cabin "Romantic Retreat" was amazing. Owner was very communicative and made our stay stress free. Even though it's listed as a romantic retreat, it was great for the family too. The cabin was well stocked with everything we needed during our stay and the hottub was definitely a hit. We cant wait for our next stay."

Secluded cabin surrounded by tall trees and a serene stream.

"The place was great ,it fit into our budget and the owners were more than helpful."

Stroll through the serene garden, surrounded by lush greenery and vibrant blooms.

"It was such a lovely stay. Everything was super tidy, clean, comfortable and cozy. We especially loved reading about the story of the build. Would absolutely recommend! "

includes taxes & fees

11 Aug - 12 Aug

Relax in this stylish room with a large L-shaped sofa, coffee table, and dining area.

"We visited in the summer…Spacious with room to spread out. Clean with all the things you need. Good communication. Laundry area a little spooky but great working laundry area."

Enjoy cooking in this well-equipped kitchen with a large island, bar stools, and stainless steel appliances.

"Beautiful house right in the village. Easy access to both Sugarbush and Killington. Would definitely stay here again. "

Surround yourself with nature's serenity, where a gentle stream flows through a lush forest, bordered by large rocks and greenery.

"Great place to stay and great host!"

includes taxes & fees

11 Aug - 12 Aug

Guests can enjoy a deck with a handrail, leading to a building with large windows.

"Beautiful area and gorgeous leaves. Liked having a weber grill."

Relax in this serene bedroom with a large bed, nightstand, and dresser, surrounded by natural light and large windows.

"Excellent location"

Two-story house with a gable roof and covered porch, featuring a front door and two upper-level windows.

"Easy drive to Middlebury Snowball, the owner was very communicative and helpful in giving tips and suggestions."

Stunning two-story house with a steeply pitched roof and inviting front porch, set amidst a beautifully manicured lawn and lush garden.

"Our stay was amazing! The house offered everything we needed, was spacious and clean. Working with the owners was also easy. Would definitely recommend and stay again!"

Kitchen features a refrigerator, microwave, oven, and sink with a faucet, along with a dining area and wooden cabinets.

"Cozy accommodations, great location, beautiful property, wonderful hosts."

Relax in a serene cabin surrounded by a fire pit and Adirondack chairs.

"Clean, comfortable, great kitchen with working pans."

includes taxes & fees

12 Aug - 13 Aug

Step up to a charming country retreat with a deck and comfortable seating area.

"Cozy and scenic property here with more than enough space, great spot with a dog, to go hiking, or just relax."

Relax on the porch with a bench and table, surrounded by a potted plant and a cozy atmosphere.

"Beautiful place."

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Top Pittsfield Hotel Reviews

Brandon Inn

10/10 Excellent

"Adorable, beautiful old hotel. Friendly, helpful staff. Great communication. Would definitely stay there again."

Best Western Inn & Suites Rutland-Killington

10/10 Excellent

"The best thing about this hotel for me was the staff. Everyone was friendly and went above and beyond to make our stay more comfortable. I will also say that this is probably the cleanest hotel pool I have ever seen, and I felt totally comfortable having my kids swim in it. I would definitely stay here again."

Lincoln Inn & Gallery

10/10 Excellent

"The owner was very attentive and helpful with all of our requests. He was truly thankful for us staying at the Inn. The Inn was nicely decorated and full of history which was shared throughout. The outside area was inviting with different seating options from couches to tables and chairs to Adirondack chairs under a tree and by the river. There was also a 2 seater swing. This is a historical building and we had to walk up about a dozen steps to our room, which may pose a problem for some. We will definitely be staying here again! I would highly recommend Lincoln Inn!"

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, apart-hotels, 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 €138 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 Farmhouse-Mountain Biking, Golf, Hiking: This holiday home rental outside of Pittsfield is located in the mountains, and has a patio, a garden and air conditioning 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Pittsfield?

Expedia has 39 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.

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Holiday Rentals in Pittsfield

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Holiday Rentals in Pittsfield

Killington Vermont Ski and Snowmobiling House

Cozy Loft for two with Hot Tub & Mtn Views

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Mountain Green

Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

Secluded retreat in the trees

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Killington Farmhouse-Mountain Biking, Golf, Hiking

Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon

5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

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

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

Comfortable mountain gem with pool, mountain views, & indoor parking space

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Top Pittsfield Hotel Reviews

Brandon Inn

The Mountain Inn at Killington

Best Western Inn & Suites Rutland-Killington

Lincoln Inn & Gallery

My Place Hotel-Randolph VT

Après Inn Killington

The Shire Woodstock

North Star Lodge and Resort

Woodstock Inn & Resort

Find out more about Pittsfield

Frequently asked questions