Pittsfield Vacation Rentals

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Vacation Rentals in Pittsfield

Killington area home - 4-seasons & hot tub. Sleeps 12+
Property grounds
Killington area home - 4-seasons & hot tub. Sleeps 12+
9.8 out of 10, Exceptional, 109 reviews
"My family and I have been renting ski homes for many years. David’s home was, by far, the cleanest property we have ever stayed at. My mother-in-law would have been impressed with the cleanliness of this home. The house was perfectly appointed and was perfect from the time we walked in until the time we left. Thank you David! We are looking forward to next year."
Killington area home - 4-seasons & hot tub. Sleeps 12+
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Interior
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, 449 reviews
"Great place to stay and get away. Everything you need in a quaint location. Loved the hot tub, seats on the porch, and having the ability to use the projector to watch sports/movies!"
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Cozy Loft for two with Hot Tub
Exterior
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, 194 reviews
"Cabin was so wonderful, fire place was lovely right next to the hot tub. Host was great with communication. Very pleasant stay. Cozy, quiet, clean cabin."
Cozy Loft for two with Hot Tub
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Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, 32 reviews
"Will be back!!"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Exterior
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, 175 reviews
"This was a great stay- thank you so much! The property was clean and serene, the house adorable and cozy and the hot tub is always a plus! It was a great area, we’ll have to visit again sometime :)"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Killington Center Inn & Suites by Killington VR - Studios
Studio | Aerial view
Killington Center Inn & Suites by Killington VR - Studios
3.0 star property
10.0 out of 10, Exceptional, 1 review
"We loved our little unit. Everything was clean and very modern. We especially loved the electric fireplace. Would stay here again. "
Killington Center Inn & Suites by Killington VR - Studios
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Desk, free WiFi, bed sheets
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
8.8 out of 10, Excellent, 38 reviews
"Great location within just a few miles of Killington base made our spring skiing getaway nice. The unit was as advertised clean with a comfortable king size bed, adequate room, and convenient parking. We especially like the privacy, nestled up top in this community off the access road. The icing on the cake for us was an excellent pool, a lab pool, and hot tub that we made grade use of enjoy your stay, will be back again!"
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
The Swirl Suite at Killington: Brand New Remodeled 1 BR/2BA Suite 142
Aerial view
The Swirl Suite at Killington: Brand New Remodeled 1 BR/2BA Suite 142
10.0 out of 10, Exceptional, 7 reviews
"We loved the condo. We stayed for a school break, family of three and it was just what we needed to unplug from our busy life. Easy to get everywhere. We will definitely rent it again on our next trip."
The Swirl Suite at Killington: Brand New Remodeled 1 BR/2BA Suite 142
Luxurious Secluded Cottage Massage Studio on Site
Fridge, microwave, oven, stovetop
Luxurious Secluded Cottage Massage Studio on Site
10.0 out of 10, Exceptional, 35 reviews
"David's place exceeded my expectations! Very smart design and layout. Quality craftmanship and attention to detail. Super clean. I wish my daughter and i could have stayed longer! Close enough to Middlebury College for this to be a great option for 2 people. David was very nice to stop by to introduce himself and see if we needed anything. We didn't see him again, but knew he was only a phone call away. Perfect."
The price is CA $225
CA $330 total
includes taxes & fees
Jun 10 - Jun 11
Luxurious Secluded Cottage Massage Studio on Site
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Property grounds
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
9.8 out of 10, Exceptional, 27 reviews
"Spacious and well kept....everything needed for for a fantastic group ski trip! Check in a breeze with communication from the owner. We look forward to a return trip!"
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Stetson Hollow Cabin by Stetson Brook
Living area
Stetson Hollow Cabin by Stetson Brook
9.8 out of 10, Exceptional, 123 reviews
"My wife, dog, and I had a wonderful stay at Jill and John’s cabin. The cabin was clean and comfortable. The hosts were very responsive to our needs. We wouldn’t hesitate to return! Thank you Jill and John!"
The price is CA $327
CA $625 total
includes taxes & fees
Jun 9 - Jun 10
Stetson Hollow Cabin by Stetson Brook
Doc's Lake house 1st floor, 2 bedroom apartment
Exterior
Doc's Lake house 1st floor, 2 bedroom apartment
10.0 out of 10, Exceptional, 55 reviews
"We really enjoyed staying at this cozy, well-equipped lake house. Everything was available to make the stay an enjoyable one. The driveway entrance and property were cleared for our arrival following a significant snowstorm. Communicating with the owner was a pleasure, with every a phone call or text message answered. Who would’ve thought seeing the solar eclipse of 2024 would be so easy and exciting! It was the owner and accommodations that made it all possible for planning the trip. We truly...
Doc's Lake house 1st floor, 2 bedroom apartment
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Fridge, microwave, oven, stovetop
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
8.6 out of 10, Excellent, 7 reviews
"The home is charming, immaculate and amidst woods with no neighbors in eye or earshot. It is on a dirt road, so an awd vehicle is a good idea. A stream runs along the driveway. The Ottauquechee River is across the road. The bathroom is on the first floor, and bedrooms on the second floor. The smoke detector goes off if you saute on the stove. I recommend learning how to turn off a wired in smoke detector. You should open the kitchen window when you saute, because most of the smoke detectors...
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Outdoor spa tub
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
10.0 out of 10, Exceptional, 12 reviews
"Nothing but positive things to say about the house. Would stay there again."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
edgemont 3 bedrooms wood fireplace updated baths ski home on shuttle sleeps 8
Exterior
edgemont 3 bedrooms wood fireplace updated baths ski home on shuttle sleeps 8
9.4 out of 10, Exceptional, 56 reviews
"We came into town to see our friend play a two night show at Pickle Barrel. The place was perfect. Check in info was thorough and easy. Kim was great. She was responsive to communications and very accommodating. Would definitely stay here or one of her other properties again!"
edgemont 3 bedrooms wood fireplace updated baths ski home on shuttle sleeps 8
Rustic home with a private hot tub, fireplace, cable, & washer/dryer
TV, fireplace, DVD player
Rustic home with a private hot tub, fireplace, cable, & washer/dryer
9.6 out of 10, Exceptional, 46 reviews
"Great house! Small issue with getting into the place with the keybox, but was quickly resolved. We had a great time, it was so comfy, great place to come home after a long day of skiing, exploring, etc. Lots of room to spread out with the family and nighttime hot tub soaks in the cold air were so refreshing!"
Rustic home with a private hot tub, fireplace, cable, & washer/dryer
Classic Vermont Cabin on 2.5 acres Lake Frontage
Classic Vermont Cabin on 2.5 acres Lake Frontage
9.8 out of 10, Exceptional, 92 reviews
"We can not say enough wonderful things about our stay. Brian was there to meet us and do a walk though of the property and even helped us out with local places to go. He is a gem! Although it rained it was absolutely perfect. The yard gave our pups a place to run free but there was also cute areas to walk them all around the area. The views of the water are incredible. Just sad it was too cold to jump in... maybe next time. October was the perfect time to see all the leaves changing and breathe...
Classic Vermont Cabin on 2.5 acres Lake Frontage
Location! Location! 1BR/1BA Steps to Mountain. 3E3
Exterior
Location! Location! 1BR/1BA Steps to Mountain. 3E3
9.4 out of 10, Exceptional, 12 reviews
"Location was great and the accommodations were perfect. The listing was a bit inaccurate in that the fireplace doesn’t work, the on site restaurant wasn’t open, no ability to get coffee or snacks, and parking was far from the unit."
Location! Location! 1BR/1BA Steps to Mountain. 3E3
Dog-friendly, lakefront home with large yard, firepit, canoe, and fireplace
Dining
Dog-friendly, lakefront home with large yard, firepit, canoe, and fireplace
9.6 out of 10, Exceptional, 4 reviews
"Really enjoyed our stay. Beautiful location and truly relaxing"
Dog-friendly, lakefront home with large yard, firepit, canoe, and fireplace
Roomy farmhouse with private hot tub, firepit, pool table, sunroom, & woodstove
TV, fireplace, video games, stereo
Roomy farmhouse with private hot tub, firepit, pool table, sunroom, & woodstove
8.8 out of 10, Excellent, 18 reviews
"The house was really quite great - especially for a winter getaway. It had everything you could possibly need and then some! My only critique was how difficult it was to communicate with the host. It feels very automated and difficult to get even the simplest answers."
Roomy farmhouse with private hot tub, firepit, pool table, sunroom, & woodstove
Don't see what you're looking for?
See all available properties in Pittsfield
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.

Pittsfield Vacation Rental Travel Info

Number of vacation rentals
80
Popular accommodation
Pittsfield private vacation homes
Known landmarks
Pico Mountain at Killington Ski Resort, Gifford Woods State Park and Fire Tower
International airports
Lebanon, NH (LEB-Lebanon Municipal) and Springfield, VT (VSF-Hartness State)

Other types of properties in Pittsfield you may be interested in

Killington area home - 4-seasons & hot tub. Sleeps 12+
Property grounds
Killington area home - 4-seasons & hot tub. Sleeps 12+
9.8 out of 10, Exceptional, 109 reviews
"My family and I have been renting ski homes for many years. David’s home was, by far, the cleanest property we have ever stayed at. My mother-in-law would have been impressed with the cleanliness of this home. The house was perfectly appointed and was perfect from the time we walked in until the time we left. Thank you David! We are looking forward to next year."
Killington area home - 4-seasons & hot tub. Sleeps 12+
Killington Mountain Lodge, Tapestry Collection by Hilton
Terrace/patio
Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 star property
7.4 out of 10, Good, 1,000 reviews
"Nice hotel close to Killington. Utilized the jacuzzi outside. There was live music in the bar. "
The price is CA $189
CA $208 total
includes taxes & fees
Jun 10 - Jun 11
Killington Mountain Lodge, Tapestry Collection by Hilton
Comfort Inn Trolley Square
Indoor pool
Comfort Inn Trolley Square
2.5 star property
8.0 out of 10, Very good, 1,004 reviews
"Easy access. Clean. Quiet. "
The price is CA $193
CA $212 total
includes taxes & fees
Jun 16 - Jun 17
Comfort Inn Trolley Square
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.

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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsfield vacation rentals we have selected for you start as low as CA $225 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 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. 

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?

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi: This vacation home rental outside of Pittsfield offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a spa tub.

How many vacation rentals are there in Pittsfield?

Expedia has 25 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 Gifford Woods State Park. In the larger area, you’ll find Appalachian Trail Adventures and Green Mountain National Golf Course.

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.

Recent reviews of Pittsfield properties
Expedia verified reviews

Woodstock Inn & Resort

Woodstock Inn & Resort

5/5 Excellent
"Beautiful hotel and great location!"
A verified traveller stayed at Woodstock Inn & Resort
Posted 1 day ago
Woodstock Inn & Resort