Pittsfield Vacation Rentals from $218: Search Short-Term Rentals

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

Killington area home - 4-seasons, hot tub and A/C : This highly rated vacation home rental in Pittsfield is located in the mountains and has a fireplace, a balcony, and a barbecue grill 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. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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In two weeks

In two months

In three months

In four months

Our top choices for Pittsfield vacation rentals

1. Robert Frost Mountain Cabins

Ripton

Joe

$341 nightly

Sep 30 - Oct 1

Total with taxes and fees

2. Killington Center 531

Killington

3. Mountain Green

Killington

Keith

$212 nightly

Sep 20 - Sep 21

Total with taxes and fees

4. The Suites at Killington Center

Killington

$364 nightly

Oct 12 - Oct 13

Total with taxes and fees

Apartment (1 Bedroom) | 1 bedroom, bed sheets

5. Cozy Hotel Room Style Studio Condo With Pool

Killington

6. Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country

Killington

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Top Pittsfield Hotel Reviews

The Jackson

10/10 Excellent

"Love staying in this beautiful hotel had very comfy beds and made us feel like we were in the heart of New England"

Woodstock Inn & Resort

8/10 Good

"Woodstock itself is absolutely beautiful and has a wonderful atmosphere. However, we had a few issues in both common areas, and our room that significantly impacted our experience. First, the cleanliness of the lobby was disappointing. I noticed that it was noticeably dusty and had visible spiderwebs in several areas, which did not create a welcoming first impression. Second, the bathroom and bed did not live up to the luxurious standard expected. Both the bathroom sink and bathtub drained incredibly slowly. This resulted in an unpleasant backflow of water whenever I tried to use them, which felt very unhygienic. Lastly, the bed was lopsided and very uncomfortable. The boxspring on both sides of the bed was covered in stains, which took away from the charm and comfort of the room. Everything else was great, and with a little more attention to room cleanliness, this place would be flawless."

My Place Hotel-Randolph VT

10/10 Excellent

"I totally dislike all the vinyl flooring that all the hotels are using these days. They don’t know how to clean them right they’re always sticky or they don’t sweep the floors properly, etc. So needless to say when I saw nice clean thick carpeting in the room except for the kitchen and bathroom, I was very happy. The bathroom was sparkling. Everything was clean & new. Hopefully it will stay that way since the hotel is only two years old. I was also happy to see a very clean laundry room with 3 washers & 3 dryers with a reasonable price, The only problem was the dryers dont dry well on high anyway. I had to dry twice. Staff - nighttime and morning, all very friendly and accommodating. They even had comfortable beds. Most hotel beds are too hard or to sunk in. Not the case here and I did not wake up with a backache like I usually do @ most hotels. There is plenty of free parking. Beautiful location as well."

Find out more about Pittsfield

Everything you need to know about Pittsfield vacation rentals

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

Pittsfield vacation 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 low season months. For more hustle and bustle, you may prefer to visit Pittsfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $218 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pittsfield rentals

At Expedia, we put the best Pittsfield vacation 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 vacation.

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.

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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 area home - 4-seasons, hot tub and A/C: This highly rated vacation home rental in Pittsfield is located in the mountains and has a fireplace, a balcony, and a barbecue grill 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. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Pittsfield?

Expedia has 28 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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Check prices for these dates

Our top choices for Pittsfield vacation rentals

1. Robert Frost Mountain Cabins

2. Killington Center 531

3. Mountain Green

4. The Suites at Killington Center

5. Cozy Hotel Room Style Studio Condo With Pool

6. Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country

Find vacation rentals that suit your style

Top Pittsfield Hotel Reviews

The Jackson

Mountain Meadows Lodge

Days Inn by Wyndham Rutland/Killington Area

Woodstock Inn & Resort

On The River Inn

My Place Hotel-Randolph VT

The Mountain Inn at Killington

Brandon Inn

The Shire Woodstock

Find out more about Pittsfield

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