Pittsfield Holiday Rentals: Short-Term Accommodations for Rent

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

Roundabout Ridge : This holiday home rental outside of Pittsfield is located in the mountains, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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In two weeks

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Our top choices for Pittsfield holiday rentals

Condo in Killington

HK$5,116 total

includes taxes & fees

16 Mar - 17 Mar

Condo in Killington

HK$6,283 total

includes taxes & fees

5 Mar - 6 Mar

Apartment in Killington

HK$9,057 total

includes taxes & fees

1 Mar - 2 Mar

Condo resort in Killington

Raul

HK$1,961 total

includes taxes & fees

11 Mar - 12 Mar

Cabin in Ripton

Joseph

HK$2,236 total

includes taxes & fees

1 Mar - 2 Mar

Apartment in Killington

Jing

HK$7,535 total

includes taxes & fees

1 Mar - 2 Mar

Holiday Home in Killington

Condo in Killington

HK$10,780 total

includes taxes & fees

5 Mar - 6 Mar

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Condos

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Top Pittsfield Hotel Reviews

Comfort Inn Rutland - Killington

10/10 Excellent

"Nice front desk staff. Pretty good breakfast."

Summit Lodge

10/10 Excellent

"It’s a great lodge. This place has a lot of character. So beautiful inside and out. Rooms are very clean. Updated bathrooms. Hot tub was amazing especially after all day skiing. Bar and bar staff was awesome. Very helpful. Breakfast was one of the best tasted open buffets. Sausage and bacon were the best. I highly recommend this place. We definitely come again ! "

Emrose Luxury Cabins

10/10 Excellent

"We had such an amazing stay at these cabins—truly the perfect start to an unforgettable weekend. We were in town for a ski trip, and with our friend planning to propose, this cabin was the ideal setting to set the mood the night before. The atmosphere was cozy, romantic, and exactly what we hoped for. Each cabin has its own special feel and unique architecture, which made the experience even more memorable and charming. The cabins are conveniently located, and we loved that there are hot tubs spread throughout the property. The hosts were incredibly responsive and helpful from start to finish, especially with food recommendations. When we let them know we were on our way, they even had the hot tub heating up and ready for us upon arrival, which was such a thoughtful touch. I also reached out ahead of time to ask if two cabins next to each other could be accommodated, and they were beyond helpful and made the process so easy. You can really tell they care about their guests’ experience. Helpful tips for future guests: bring slippers to wear inside the cabins since no shoes are allowed, and definitely bring a robe for the walk to the hot tub—it makes the experience even better! We couldn’t have asked for a better stay and would absolutely recommend these cabins to anyone looking for a relaxing, memorable getaway. ⭐️⭐️⭐️⭐️⭐️"

My Place Hotel-Randolph VT

10/10 Excellent

"This was a great hotel. I went for a three day weekend. It doesn't have a pool or a gym but other than that, it was a superb place to stay. The rooms were clean with kitchenettes (but no items to cook with so bring your own.) They are pet friendly and have a dog walk around the property. They offer coffee and tea throughout the day which was so nice after a day of being out in the cold. The staff was very friendly. I would highly recommend this place and I plan on staying here again. "

Find out more about Pittsfield

Search for holiday rentals in Pittsfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Pittsfield using one of the methods below:

View our selection of featured holiday rentals in Pittsfield
Use the map to find apartments and other holiday homes in the Pittsfield neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in Pittsfield while they last

Look no further and take a look at our great range of rental properties in Pittsfield!

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?

Roundabout Ridge: This holiday home rental outside of Pittsfield is located in the mountains, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Pittsfield?

Expedia has 28 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. Pittsfield Town Hall and Roger Clark Memorial Central Library 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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Check prices for these dates

Our top choices for Pittsfield holiday rentals

Condo in Killington

Condo in Killington

Apartment in Killington

Condo resort in Killington

Cabin in Ripton

Apartment in Killington

Holiday Home in Killington

Condo in Killington

Condo in Killington

Holiday Home in Killington

Holiday Home in North Sherburne

Condo in Killington

Holiday Home in Killington

Condo in Killington

Find holiday rentals that suit your style

Top Pittsfield Hotel Reviews

Comfort Inn Rutland - Killington

The Mountain Inn at Killington

Killington Mountain Lodge, Tapestry Collection by Hilton

Best Western Inn & Suites Rutland-Killington

North Star Lodge and Resort

Summit Lodge

Emrose Luxury Cabins

Woodstock Inn & Resort

My Place Hotel-Randolph VT

Find out more about Pittsfield

Frequently asked questions

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