Holiday Rentals in Pittsfield

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Holiday Rentals in Pittsfield

Killington Vermont Ski and Snowmobiling House

9.2 out of 10, Wonderful, (44)
"Spacious and nice location. The home met our needs. Basic home with some necessities lacking like soap, shampoo, washcloths, and paper towels. Coffee maker did not function well. Cooking utensils could use an upgrade. Needs a thorough cleaning and we noticed this right away upon arrival. Hot tub did not seem to work. No air conditioning, which should be clearly noted in the property description."
Killington Vermont Ski and Snowmobiling House

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (49)
"Private and great location. Communication was amazing. For the price it felt like an absolute steal. Will definitely be going back in the winter for a ski trip. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (262)
"Great location, marvelous host, terrific property! I'll be returning for sure!"
Cozy Loft for two with Hot Tub & Mtn Views

Mountain Green

2.0 star property
6.6 out of 10, (13)
"Great communication from Jeff."
The price is €229
includes taxes & fees
13 Oct - 14 Oct
Mountain Green

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

10.0 out of 10, Exceptional, (516)
"We just love the quiet and beauty of the area. We love to come here because our hosts very easy to communicate and enjoy being on vacation."
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

10.0 out of 10, Exceptional, (63)
"Very clean, cozy environment. Property owner was very nice and helped with any questions we had. 100% would book again!!"
The price is €169
includes taxes & fees
16 Oct - 17 Oct
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

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

9.0 out of 10, Wonderful, (54)
"Cozy but all the amenities, great location"
The price is €149
includes taxes & fees
20 Oct - 21 Oct
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

Killington Retreat

2.0 star property
9.6 out of 10, Exceptional, (13)
"Had a great time staying so close to Killington. Sauna, hot tub and pool were a great way to warm up after a day of skiing."
Killington Retreat

Trail Creek 41 | Condo in Killington near lifts/hiking with pool & rec room

9.2 out of 10, Wonderful, (16)
"Me and my friends stayed here for a week. It was clean when we got there. The pool and hot tub were really nice. Over all it was a nice stay and we enjoyed the area!!"
Trail Creek 41 | Condo in Killington near lifts/hiking with pool & rec room

Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVE

9.6 out of 10, Exceptional, (92)
"This condo provided everything we needed for a nice stay of skiing. We very much enjoyed our stay."
Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVE

Vineyard Cabin

10.0 out of 10, Exceptional, (4)
"Cozy cabin, pet friendly, lovely views! "
Vineyard Cabin

Stetson Hollow Cabin by Stetson Brook

9.8 out of 10, Exceptional, (156)
"My best friend and I came to the cute cabin. We got to see lots of Vermont items that are nearby. "
The price is €384
includes taxes & fees
19 Oct - 20 Oct
Stetson Hollow Cabin by Stetson Brook

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (222)
"Was a nice place to unwind and unplug from the city over the holiday weekend. Very clean and was homey. "
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

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

8.0 out of 10, Very good, (35)
"Convenient for skiing and visiting the greater VT area. Unit has what you need for your stay."
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Glamping hut with WiFi in Ripton, biking, hiking, skiing

The price is €146
includes taxes & fees
9 Oct - 10 Oct
Glamping hut with WiFi in Ripton, biking, hiking, skiing

🌺Luxury Estate🌳 25 Gorgeous Acres of Privacy 🌳Family Getaway🌳Swimming Pond🌺

9.8 out of 10, Exceptional, (15)
"The Property and surrounding country were spectacular and me and my family and our pets had a lovely time. If you love the outdoors and staying in a wonderful home this is the place!"
🌺Luxury Estate🌳 25 Gorgeous Acres of Privacy 🌳Family Getaway🌳Swimming Pond🌺

MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

10.0 out of 10, Exceptional, (72)
"Great spot, top end house! ATV tour excellent "
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

Nana's House

10.0 out of 10, Exceptional, (46)
"I'm not much for reviews, but everything about this place was perfect! We can't wait to go back!"
Nana's House

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

3.0 star property
9.4 out of 10, Exceptional, (15)
"Very nice townhouse."
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

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

2.0 star property
9.8 out of 10, Exceptional, (77)
"The feel was so relaxing, felt like home.Im at a loss for words was just wonderful."
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pittsfield Hotel Reviews

Find out more about Pittsfield

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 €146 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 Vermont Ski and Snowmobiling House: This highly rated holiday home rental in Pittsfield is located near skiing, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

How many holiday rentals are there in Pittsfield?

Expedia has 31 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.