Pittsfield Vacation Rentals from ￥9,297: Search Short-Term Rentals

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

Killington Farmhouse-Mountain Biking, Golf, Hiking : This vacation 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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Vacation 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. "

￥34,789 total

includes taxes & fees

Aug 17 - Aug 18

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! "

￥23,139 total

includes taxes & fees

Aug 11 - Aug 12

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!"

￥47,158 total

includes taxes & fees

Aug 17 - Aug 18

Cozy cabin interior with a stone fireplace, wooden beams, and a comfortable seating area.

"Loved the cabin. Great access to Sugarbush and all the MR valley has to offer. The hosts could not be nicer."

￥64,306 total

includes taxes & fees

Aug 18 - Aug 19

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."

￥40,177 total

includes taxes & fees

Aug 10 - Aug 11

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

The Mountain Inn at Killington

10/10 Excellent

"Great place to stay, so close to the mountain, rode my bike all weekend. Clean comfortable room and the staff treated us like family. Highly recommended. Thanks!"

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!"

Cozy Loft for two with Hot Tub & Mtn Views

10/10 Excellent

"Perfect size to spend a couple days taking in the nature of Vermont. Has everything you need for the perfect weekend. The host responded very quickly throughout the booking process and during the stay. If you like what you see, you’re gonna have a great trip here!"

Find out more about Pittsfield

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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 Farmhouse-Mountain Biking, Golf, Hiking: This vacation 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Pittsfield?

Expedia has 39 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.

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Pittsfield Vacation Rentals

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Vacation 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

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

Stetson Hollow Cabin by Stetson Brook

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

The Mountain Inn at Killington

Best Western Inn & Suites Rutland-Killington

Lincoln Inn & Gallery

My Place Hotel-Randolph VT

Cozy Loft for two with Hot Tub & Mtn Views

Après Inn Killington

The Shire Woodstock

Brandon Inn

North Star Lodge and Resort

Find out more about Pittsfield

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Frequently asked questions