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May 10 - May 11
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May 11 - May 12
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May 10 - May 12

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Compare 1,621 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Exterior
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (193)
"Cozy, welcoming environment. We enjoyed the privacy and quietness of the location. Jeff was very responsive and pleasant. We would definitely recommend to anyone looking for the tiny home experience and would certainly stay there again."
Cozy Loft for two with Hot Tub
Property grounds
Cozy private country setting - 15 miles from Woodstock
10.0 out of 10, Exceptional, (17)
"The pictures do not do this cabin justice, it is spotless, equipped with everything you could need and more and perfect. Melanie is an amazing hostess and we cannot wait to come back to Vermont and stay there again. Thanks so much Melanie :)"
Cozy private country setting - 15 miles from Woodstock
Fridge, microwave, oven, stovetop
Easy access to VAST snowmobile trail system and local mountain bike trails
10.0 out of 10, Exceptional, (10)
"Well kept and well managed. Just what I hoped for and I would recommend it, but that's with mixed feelings because I want it to be available next year (want it to remain my secret, oh well). Like most of rural VT no cell service, but wi-fi calling worked for me in this flat. Great coffee and sandwich place 1.3 mi north, outside seating."
Easy access to VAST snowmobile trail system and local mountain bike trails
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Interior
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (445)
"Cute little property with great host communication. We will be back!"
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Microwave, oven, stovetop, dishwasher
Authentic farmhouse for those who love cozy, quirky, historical imperfection
10.0 out of 10, Exceptional, (1)
"Lot's of room. Quiet. Close to things. Great living room. I wish that mine was so comfortable. When you drive up, it looks a little rough, but it is nice inside. Dining room table seats ten. Nice stove top. Dual ovens."
The price is $234
$475 total
includes taxes & fees
May 12 - May 13
Authentic farmhouse for those who love cozy, quirky, historical imperfection
Living area | Smart TV, fireplace, books, offices
Cottage in Barnard
10.0 out of 10, Exceptional, (15)
"Loved the cozy atmosphere and the heated tiles in the kitchen!"
Cottage in Barnard
Property grounds
Secluded retreat in the trees
10.0 out of 10, Exceptional, (5)
"My family, partner and I stayed for a week in the cozy cabin for the total solar eclipse. We have family in Vermont and this was the perfect stay nearby. The cabin was exactly as described and had everything one could ask for. Our hostess, Hannah and cyrus were friendly and provided recommendations of things.to do nearby. We also took a short walk on their 26 acre property on our last day which was lovely. We highly recommend staying at the cabin if anyone wants.to get away and disconnect from...
Secluded retreat in the trees
Property grounds
Historic Vermont Ski House w/ Mountain Views!
10.0 out of 10, Exceptional, (1)
"My husband and I along with our 12 yr old Maltipoo enjoyed a long weekend at this home. It was well maintained, and had more than enough room (3 bedrooms and two full bathrooms.) The area was beautiful, and the house sits on over 300 acres. Everything we needed was in the house, and there were great farmer's markets in the area, and just as the leaves were changing colors there were fantastic views. Thanks for Jen & Brett for sharing your home."
Historic Vermont Ski House w/ Mountain Views!
Exterior
VAST trail access with peaceful views & cozy spaces in VT schoolhouse.
10.0 out of 10, Exceptional, (4)
"House was centrally located about 30 minutes from everything we needed. Very clean and comfortable, well stocked. Even though owner said that there was no cell coverage had good coverage with AT&T. Would definitely rent from them again."
VAST trail access with peaceful views & cozy spaces in VT schoolhouse.
Property grounds
Historic Schoolhouse in Rural Vermont Beauty Spot
10.0 out of 10, Exceptional, (19)
"We stayed for 4 nights, having come from the UK to visit family in Vermont. Excellent communication with Terrie before our trip and Philip visited soon after our arrival to peronally welcome us. Peaceful, comfortable and comprehensively equipped, it was perfectly located for access to town and for exploring the local area. As a retired primary teacher, it was wonderful to see all the old school furniture, equipment and books."
Historic Schoolhouse in Rural Vermont Beauty Spot
Exterior
Spectacular Mountain Views, 6 Bedroom, 4 Bath with Fireplace, Hot Tub & Elevator
10.0 out of 10, Exceptional, (7)
"Our group of 12 (6 adults and 6 children) enjoyed a lovely long weekend at this beautiful property. As 3 separate families we greatly appreciated the shared space as much as the configuration of each floor that allowed for time away from each other when preferred. Barry is incredibly responsive and went out of his way to ensure that we were comfortable. The house is incredibly clean, comfortable and well maintained. We are already taking about a return in the spring or fall to appreciate its...
Spectacular Mountain Views, 6 Bedroom, 4 Bath with Fireplace, Hot Tub & Elevator
Exterior
Stunning Log Home, 7 Bed/4 Bath. Mountain View!
10.0 out of 10, Exceptional, (21)
"The house is beautiful and spacious for large groups. We had a great time even though the weather did not help. Scott was helpful at all times."
Stunning Log Home, 7 Bed/4 Bath. Mountain View!
Fridge, microwave, stovetop, coffee/tea maker
Pet-Friendly Roxbury Farmhouse on 350 Acres!
10.0 out of 10, Exceptional, (2)
"Owners are super nice. We really enjoyed our stay."
Pet-Friendly Roxbury Farmhouse on 350 Acres!
Living area | Fireplace, books
Stetson Hollow Cabin by Stetson Brook
9.8 out of 10, Exceptional, (122)
"Stayed here to access the Sugarbush ski area. Easy 10-15 minute drive with on-site parking at cabin. Super cute with fire wood provided for use in both the inside fire place and outside fire pit. Cabin abuts the river which makes a nice coffee spot. Easy access to hiking trails. Only things to consider is that beds require climbing a ladder to access so keep that in mind if people have mobility issues. Also no TV so bring your own device if you have something you would like to watch."
The price is $240
$458 total
includes taxes & fees
May 12 - May 13
Stetson Hollow Cabin by Stetson Brook
1 bedroom, iron/ironing board, travel crib, free WiFi
Cozy Cabin Retreat
9.8 out of 10, Exceptional, (19)
"Wonderful place, just need to fill in holes and level the driveway out, especially at the garage. Hope to stay again one day, but I plan on driving my corvette next time, which sits low to the ground. Also, they are serious about no cellular service, but I enjoyed the quietness without my phone working."
Cozy Cabin Retreat
Fridge, microwave, oven, stovetop
Run, ride, hike and swim in Central Vermont
9.8 out of 10, Exceptional, (8)
"Everything was excellent. Thank you John."
Run, ride, hike and swim in Central Vermont
Exterior
Perfect secluded cozy getaway pet friendly home Hawk Landing
9.8 out of 10, Exceptional, (18)
"We came to Vermont for the Fall foliage and hiking. The home at Hawk's Landing was perfectly located for this and exceeded my expectations. I would not hesitate to rent this property again."
Perfect secluded cozy getaway pet friendly home Hawk Landing
Fridge, microwave, oven, stovetop
Lori and Dean's Killington Ski House with Wi-Fi
9.6 out of 10, Exceptional, (30)
"Picked it for proximity to Killington and Sugarbush, size and hit tub access. All worked out very well. And Dean was very helpful including amazing overnight snow removal. Would certainly come back."
Lori and Dean's Killington Ski House with Wi-Fi
Smart TV, fireplace
Killington Vermont Ski and Snowmobiling House
9.4 out of 10, Exceptional, (41)
"plenty of room for 2 families"
Killington Vermont Ski and Snowmobiling House
Property grounds
Delightful Retreat W/ Firepit, Wooded Surroundings, and Free WiFi
9.2 out of 10, Wonderful, (10)
"One of a kind vacation home. 1.8 mile of dirt roads leading to a home with great view. A true Vermont experience. Would love to come back."
Delightful Retreat W/ Firepit, Wooded Surroundings, and Free WiFi
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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.

Frequently asked questions

Where is the best place to stay in Pittsfield?

Located 9.5 mi (15.3 km) from the heart of Pittsfield, Killington Mountain Lodge, Tapestry Collection by Hilton is a top choice for your stay based on our traveler data. Other good choices for your stay in the area are North Star Lodge and Resort and Days Inn by Wyndham Rutland/Killington Area. See all available top hotels, or vacation rentals in Pittsfield.

What's the top vacation rental in Pittsfield?

Rustic Roxbury Ski Farmhouse with Trails!: This vacation home rental near Pittsfield offers a patio, a private yard, 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 and your friends and family can relax into your vacation with amenities like a selection of games. See all vacation rentals in Pittsfield.

If I need to cancel my hotel reservation in Pittsfield, will I receive a refund?

Yes, the majority of hotel reservations are fully refundable if cancelled before the hotel’s cancellation deadline, which is often 24 or 48 hours before your check-in date. If you booked a non-refundable reservation, you may still be able to cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Pittsfield.

Where can I learn more about changing or cancelling my trip to Pittsfield?

To find more details about changing or cancelling your trip to Pittsfield, go to https://www.expedia.com/service/.

What's the best budget-friendly hotel in Pittsfield?

Based on reviews, Clear River Inn is a popular inn for our travelers who want a more economical choice, and features free WiFi and free parking. View all budget hotels in Pittsfield.

What's the best pet-friendly place to stay in Pittsfield?

Clear River Inn is a top dog-friendly inn, and offers a restaurant and a nightclub for its human guests. See more pet-friendly hotel accommodations in Pittsfield.

What are some accommodations with pools in Pittsfield?

North Star Lodge and Resort: Hotel located near Killington Resort. Features a sauna, an outdoor pool, and free self parking. The Mountain Inn at Killington and Woodstock Inn & Resort are a couple of other choices with an onsite pool. View all hotels with pools in Pittsfield.

What is the best spa hotel in Pittsfield?

Sweet Life - Vermont Chalet - 6 Person Indoor Hot Tub - 15 min to Killington is a top spa hotel with an arcade/game room, barbecue grills, and billiards/pool table. Kick back and relax in the spa tub. Other popular spa hotels in Pittsfield include Newly Built Killington Vermont Ski House and Sweet Life - GetAway.

What's the best accommodation near Rutland Southern Vermont Regional Airport (RUT)?

Comfort Inn Trolley Square is one of the top choices for your stay and is a popular hotel, featuring free breakfast and an indoor pool. It's located 4.9 mi (7.8 km) from Rutland Southern Vermont Regional Airport. Other choices near the airport include Holiday Inn Rutland-Killington Area and Quality Inn Rutland.

What's it like to stay in Pittsfield?

Visitors can enjoy all that Pittsfield has to offer including the bars and restaurants. This city also attracts tourists with its welcoming locals. In Pittsfield, there are 31 hotels and other accommodations to choose from. Find out more about Pittsfield.

What should I see while I'm in Pittsfield?

Places to visit in the wider area include Appalachian Trail Adventures, Green Mountain National Golf Course, and Gifford Woods State Park. You'll also find Pico Mountain at Killington Ski Resort and Pico Peak in the area. Check out what more to see and do in Expedia's Pittsfield guide.

What's the seasonal weather like in Pittsfield?

The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 23°F. The snowiest months in Pittsfield are January, March, February, and April, with each month seeing an average of 10 inches of snowfall.