Pittsfield Holiday Rentals from €145: Search Short-Term Rentals

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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Our top choices for Pittsfield holiday rentals

The Suites at Killington Center

Killington

includes taxes & fees

2 Mar - 3 Mar

Mountain Green Resort by Killington VR - 2 Bedrooms

Killington

Mountain Green 3G6

Killington

includes taxes & fees

1 Mar - 2 Mar

Mountain Green

Killington

Raul

includes taxes & fees

11 Mar - 12 Mar

Robert Frost Mountain Cabins

Ripton

Joseph

includes taxes & fees

1 Mar - 2 Mar

Mountain Green Resort

Killington

Jing

includes taxes & fees

1 Mar - 2 Mar

Pico Mountain Condo F106 3 Bedroom Home

Killington

includes taxes & fees

1 Mar - 2 Mar

Sunrise Bear Ridge C4 4 Bedroom Condo

Killington

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Top Pittsfield Hotel Reviews

The Mountain Inn at Killington

10/10 Excellent

"We lover our stay at The Mountain Inn at Killington. It's close enough to walk to main Lift Snowshed about 7-10 minutes walk but they have free shuttle service upon calling for any pickups. If you own EV car, they got charging station about 3 minutes walk away on level 2 charger but is not free, 30 cents per kw for tesla but more for other EV at 50 cents I believe. Their continental breakfast is great but no eggs or proteins however it is best with begal and danish and cereal, Oatmeal and COFFEE. Oh free water bottle so you can bring one to the slopes too. I would stay there again and again. They got heated outdoor small pool for relaxing after long day or awesome skiing/boarding. The only negative is their restaurant, not bad but expensive dinning option. pretty costly for good but not great food. Service was super of course"

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. ⭐️⭐️⭐️⭐️⭐️"

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 €145 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?

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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