Find hotels in Pittsfield, VT from AED 239

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Check Pittsfield hotel prices

Tonight
22 Dec - 23 Dec
Tomorrow night
23 Dec - 24 Dec
Next weekend
27 Dec - 29 Dec

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Compare 1,637 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

My Place Hotel-Randolph VT
Exterior

My Place Hotel-Randolph VT

2.0 star property
9.4 out of 10, Exceptional, (86)
"Super clean room, very comfortable bed, great shower. Nice to have coffee and tea available in the lobby. Would have been nice to have a reading lamp on the other side of the bed as well. But all in all, a great place to use as a base for exploring the region. "
The price is AED 426
AED 465 total
includes taxes & fees
14 Jan - 15 January 2025
My Place Hotel-Randolph VT
Off Grid Glamping Shed with River Access
Property grounds

Off Grid Glamping Shed with River Access

2.0 star property
The price is AED 239
AED 370 total
includes taxes & fees
24 Dec - 25 Dec
Off Grid Glamping Shed with River Access
Adorable Cozy Tiny House perfect for skiing Vermont.
Interior

Adorable Cozy Tiny House perfect for skiing Vermont.

2.0 star property
8.8 out of 10, Excellent, (13)
"Nice and close to the White River and was very comfortable "
The price is AED 257
AED 370 total
includes taxes & fees
24 Dec - 25 Dec
Adorable Cozy Tiny House perfect for skiing Vermont.
ROMANTIC SPIRITUAL FAIRYTALE EUROPEAN TYPE COWBOY/INDIAN CASTLE
Point of interest

ROMANTIC SPIRITUAL FAIRYTALE EUROPEAN TYPE COWBOY/INDIAN CASTLE

5.0 out of 10, (2)
"My husband and I stayed here for one night during this beautiful fall season. Peter met us when we arrived and showed us around and was very accommodating. The layout of the church is wide open. With antiques, unique collectibles, and interesting artifacts that were placed to be aesthetic to the eye. Yes, there were antique knives and antique toy guns, which added to the unique character of this VRBO. The feel of the house is that it is much loved and there is much thought into what goes in it...
The price is AED 2,755
AED 3,525 total
includes taxes & fees
24 Dec - 25 Dec
ROMANTIC SPIRITUAL FAIRYTALE EUROPEAN TYPE COWBOY/INDIAN CASTLE
Cozy Loft for two with Hot Tub
"This cute and cozy loft was perfect in every way!" JV

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (222)
"We had the best time at Jeff’s perfect cozy ‘little loft’! It exceeded expectations! We especially enjoyed the hot tub after long days of skiing!"
Cozy Loft for two with Hot Tub
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Property grounds

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

2.0 star property
10.0 out of 10, Exceptional, (1)
"Absolutely the best hosts! Easy to work with. Quick responses to questions. Very accommodating. Beautiful setting. Perfect getaway. The goats were great barn-mates! Outdoor fire pit was perfect! Highly recommend!"
The price is AED 441
AED 576 total
includes taxes & fees
24 Dec - 25 Dec
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Stetson Hollow Cabin by Stetson Brook
Cozy living space with fieldstone fireplace.

Stetson Hollow Cabin by Stetson Brook

9.8 out of 10, Exceptional, (134)
"Cabin had everything we needed and more. We found it to be a great location for the small day trips we did to surrounding towns. Location is just gorgeous. "
The price is AED 882
AED 1,715 total
includes taxes & fees
6 Jan - 7 January 2025
Stetson Hollow Cabin by Stetson Brook
Adventure-filled getaway, ponds, trails, dog-friendly, w/d, BBQ, views & more

Adventure-filled getaway, ponds, trails, dog-friendly, w/d, BBQ, views & more

9.2 out of 10, Wonderful, (11)
"Everything was perfect "
Adventure-filled getaway, ponds, trails, dog-friendly, w/d, BBQ, views & more
Redbrick Schoolhouse
Dining

Redbrick Schoolhouse

2.0 star property
Redbrick Schoolhouse
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
"The cabin was peaceful and everything was provided, plus some!" Stacy S

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

10.0 out of 10, Exceptional, (473)
"The cabin was amazing, the design and decor is perfect and the space is perfect. The hot tub and fire pit were so lovely in the evening, and the movie theatre was also excellent for watching TV and films. Jeff was an excellent host, super friendly and helpful and the area was lovely and quiet, very peaceful. Thanks again! "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Luxe 14-acre Vermont Countryside Lodge!
Interior

Luxe 14-acre Vermont Countryside Lodge!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This home has it all! Beautifully decorated, cozy fireplace, spacious private surroundings, the BEST claw foot bathtubs, mountain and star views magnificent! We had 12 people and the home’s size afforded us all plenty of privacy. Great stove in kitchen. Plenty of firewood stacked. Off grid living was cool! No TVs! Such a needed break from the seasonal chaos! Highly recommend ❤️"
Luxe 14-acre Vermont Countryside Lodge!
1875 Modern Renovated 7 Acres with Post & Beam Barn and Charm - Close to Skiing
Private kitchen

1875 Modern Renovated 7 Acres with Post & Beam Barn and Charm - Close to Skiing

9.4 out of 10, Exceptional, (26)
"Amazing remodel of a truly historic farmhouse. Great cooking kitchen, lots of space and located near the state capital, Montpelier. Owners immediately responsive and great to work with! We had a wonderful holiday in Vermont in this beautiful home."
The price is AED 826
AED 1,740 total
includes taxes & fees
30 Dec - 31 Dec
1875 Modern Renovated 7 Acres with Post & Beam Barn and Charm - Close to Skiing
Easy access to VAST snowmobile trail system and local mountain bike trails
Snow and ski sports

Easy access to VAST snowmobile trail system and local mountain bike trails

10.0 out of 10, Exceptional, (16)
"Our stay lasted three nights and four days. The accommodations were great, lots of room, and very comfortable. The upstairs barn apartment was cozy, quiet (nobody was in the downstairs apt), and well-situated for our itinerary. We visited 6 waterfalls, 23 covered bridges, and 4 other points of interest. We would have seen some more, but it rained a good part of one day and we skipped a few."
Easy access to VAST snowmobile trail system and local mountain bike trails
Secluded retreat in the trees
This is it! The primary living space w/ big windows and lots of light.

Secluded retreat in the trees

10.0 out of 10, Exceptional, (15)
"My husband and I needed a little getaway to decompress. This was the perfect haven for us! The place was clean and in really good shape. The big windows were lovely to look out of. We wished we had more time to explore the trail that was on the land. It was quiet, comfortable, and restful. The bed was really comfortable. The kitchen was stocked for basic cooking which was helpful. There were plenty of towels if needed. We would recommend this site for sure!"
Secluded retreat in the trees
Run, ride, hike and swim in Central Vermont
Exterior

Run, ride, hike and swim in Central Vermont

9.8 out of 10, Exceptional, (14)
"This was a nice quiet place to stay! I was in the area for a class and needed a place to stay. It was clean and comfy"
Run, ride, hike and swim in Central Vermont
Cozy renovated barn apartment on first floor
Exterior

Cozy renovated barn apartment on first floor

9.2 out of 10, Wonderful, (7)
"Beautiful setting and lovely stay!"
Cozy renovated barn apartment on first floor
Cozy Cabin Retreat
Exterior

Cozy Cabin Retreat

10.0 out of 10, Exceptional, (26)
"The property was perfect and quiet. The hosts were quick to respond and gave great directions and advice. Will definitely stay again."
Cozy Cabin Retreat
Killington ski house
Plenty of Snow and Plenty to do: outside and in!

Killington ski house

9.6 out of 10, Exceptional, (31)
"Great place, great location, great response and communication with the host, Dean. Very much appreciated. "
Killington ski house
Dreamy Artist Chalet in Secluded Historic Village
Open Kitchen area

Dreamy Artist Chalet in Secluded Historic Village

8.4 out of 10, Very Good, (5)
"My friend and I came to ride horses for two days at the Icelandic Horse Farm in Fayston, and we knew we wanted a comfortable place nearby for the night in between. The Chalet was in the perfect location between places to eat (we had pizza at the Blue Stone) and the stable. And it is LOVELY inside, beautifully furnished and stocked with everything you need, Highly recommend!"
The price is AED 999
AED 1,724 total
includes taxes & fees
5 Jan - 6 January 2025
Dreamy Artist Chalet in Secluded Historic Village
Adventure Awaits at the Alpine Apartment! Explore All Year Round!
Living room Open floor plan

Adventure Awaits at the Alpine Apartment! Explore All Year Round!

The price is AED 441
AED 921 total
includes taxes & fees
5 Jan - 6 January 2025
Adventure Awaits at the Alpine Apartment! Explore All Year Round!
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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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 Days Inn by Wyndham Rutland/Killington Area and North Star Lodge and Resort. See all available top hotels, or vacation rentals in Pittsfield.

What's the top vacation rental in Pittsfield?

Killington area home - 4-seasons & hot tub. Sleeps 12+: This highly rated vacation home rental in Pittsfield is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a spa tub so you can immerse yourself in your vacation. 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 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?

Days Inn by Wyndham Rutland/Killington Area: Features a sauna, an indoor pool, and daily. North Star Lodge and Resort and Woodstock Inn & Resort are a couple of other choices with an onsite pool. View all hotels with pools in Pittsfield.

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 40 hotels and other accommodations to choose from. Find out more about Pittsfield.

What should I see while I'm in Pittsfield?

A favorite place to visit is Green Mountain National Forest. 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 December, with each month seeing an average of 10 inches of snowfall.