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10 Oct - 12 Oct
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Cabin Rentals in Pittsfield

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, (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
Exterior

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (260)
"Great location, marvelous host, terrific property! I'll be returning for sure!"
Cozy Loft for two with Hot Tub & Mtn Views
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Exterior

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

10.0 out of 10, Exceptional, (514)
"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
Vineyard Cabin
Exterior

Vineyard Cabin

10.0 out of 10, Exceptional, (4)
"Cozy cabin, pet friendly, lovely views! "
Vineyard Cabin
Classic Vermont Cabin on 2.5 acres Lake Frontage
Exterior

Classic Vermont Cabin on 2.5 acres Lake Frontage

9.8 out of 10, Exceptional, (115)
"Visiting family in Vermont, very charming place to stay, quaint, quiet, fun in the lake, grandkids visited, great cookout, although the steps to the one bedroom were challenging for my handicapped wife, never thought a futon would be so comfortable, especially for me, at 6’2”, 260 lbs, it was great, we had loads of fun, short trips to restaurants, and another visit to Tom and Jerry’s, thanks so much, it was awesome, will be back!"
Classic Vermont Cabin on 2.5 acres Lake Frontage
Secluded retreat in the trees
Exterior

Secluded retreat in the trees

10.0 out of 10, Exceptional, (27)
"The place was great ,it fit into our budget and the owners were more than helpful."
The price is AED 463
AED 864 total
includes taxes & fees
1 Oct - 2 Oct
Secluded retreat in the trees
Stetson Hollow Cabin by Stetson Brook
Exterior

Stetson Hollow Cabin by Stetson Brook

9.8 out of 10, Exceptional, (154)
"My best friend and I came to the cute cabin. We got to see lots of Vermont items that are nearby. "
The price is AED 882
AED 1,740 total
includes taxes & fees
19 Oct - 20 Oct
Stetson Hollow Cabin by Stetson Brook
New Skye Ridge lodge Carriage house w AC and hot tub in charming Killington VT
Private kitchen

New Skye Ridge lodge Carriage house w AC and hot tub in charming Killington VT

The price is AED 1,653
AED 2,847 total
includes taxes & fees
1 Oct - 2 Oct
New Skye Ridge lodge Carriage house w AC and hot tub in charming Killington VT
Gorgeous cabin with Pack 'n Play, private dock, lovely deck, firepit, wood stove
Dining

Gorgeous cabin with Pack 'n Play, private dock, lovely deck, firepit, wood stove

9.8 out of 10, Exceptional, (12)
"We loved the cottage and the proximity to a wonderful lake!"
Gorgeous cabin with Pack 'n Play, private dock, lovely deck, firepit, wood stove
Brookside Cabin + Hot Tub | Woodstock & Killington
Exterior

Brookside Cabin + Hot Tub | Woodstock & Killington

10.0 out of 10, Exceptional, (2)
"Amazing home! So relaxing, clean, cozy, and had everything we could ever need for this trip. "
Brookside Cabin + Hot Tub | Woodstock & Killington
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Exterior

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (220)
"We had a wonderful stay! The house was extremely clean, and well organized. It has everything we need. "
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Welcoming to this cozy 3-bedroom cabin on 100 acres, in Tunbridge
Exterior

Welcoming to this cozy 3-bedroom cabin on 100 acres, in Tunbridge

Welcoming to this cozy 3-bedroom cabin on 100 acres, in Tunbridge
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Exterior

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

2.0 star property
10.0 out of 10, Exceptional, (6)
"This was the perfect mountain cabin. Everything you needed in modern day but in a cabin setting. It is in the woods but close to town. Impeccably maintained. I would come back here in a heartbeat."
The price is AED 1,127
AED 2,574 total
includes taxes & fees
10 Oct - 11 Oct
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Charming farmhouse, dog friendly, Appalachian trail access
Exterior

Charming farmhouse, dog friendly, Appalachian trail access

7.8 out of 10, Good, (6)
"A lovely "get-away" in beautiful Vermont."
Charming farmhouse, dog friendly, Appalachian trail access
Killington / Mendon CLEAN, 1 bedroom cabin
Exterior

Killington / Mendon CLEAN, 1 bedroom cabin

9.8 out of 10, Exceptional, (20)
"Nice cozy cabin. Can say without a doubt the cleanness place we have stayed at. Robert was friendly and helpful with any questions we had. The location was perfect for what we had planned. Would stay there again if ever in the area again. "
Killington / Mendon CLEAN, 1 bedroom cabin
Killington / Mendon CLEAN, 2 bedroom cabin
Exterior

Killington / Mendon CLEAN, 2 bedroom cabin

9.8 out of 10, Exceptional, (6)
"This cabin was the perfect home base for a ski weekend at Pico. The kitchen made it easy to cook and reheat food too. "
Killington / Mendon CLEAN, 2 bedroom cabin
Secluded cabin close to Warren Falls w/ porch
Exterior

Secluded cabin close to Warren Falls w/ porch

10.0 out of 10, Exceptional, (1)
"Beautiful property and house. The layout was wonderful. The house felt spacious even though it was small. The kitchen had everything we needed. The porch in back was perfect for reading. The furnishings were lovely. The proximity to Warren (2 miles) was great. The only issues were the low water pressure in the master bath shower (the large showerhead?) and a smell coming from the utility closet off of the master bedroom which we could not identify. Other than that, a perfect stay. We would like...
Secluded cabin close to Warren Falls w/ porch
The Cabin that brings people together
Exterior

The Cabin that brings people together

9.6 out of 10, Exceptional, (82)
"Had a blast staying in this beautiful cabin. Missed the teepee but couldn't have asked for a better stay!"
The Cabin that brings people together
SPRING IN THE GREEN MOUNTAINS/PET FRIENDLY-WOOF
Exterior

SPRING IN THE GREEN MOUNTAINS/PET FRIENDLY-WOOF

10.0 out of 10, Exceptional, (90)
"terrific time at this wonderful cabin. they had everything we needed to have fun on the lake."
SPRING IN THE GREEN MOUNTAINS/PET FRIENDLY-WOOF
Robert Frost Mountain Cabins
Cabin 1 (Pet Free) - Peak Perspective | Pillowtop beds, individually decorated, individually furnished

Robert Frost Mountain Cabins

3.5 star property
10.0 out of 10, Exceptional, (40)
"Owners are super helpful and cinnamon rolls were yummy. Off the beaten path and lovely"
The price is AED 1,015
AED 1,106 total
includes taxes & fees
26 Oct - 27 Oct
Robert Frost Mountain Cabins
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

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"Very easy check-in. Lovely staff, very friendly, and helpful. The only thing missing is a tea coffee maker in the room. Otherwise, everything else is excellent."
Patricia 1-night trip
Posted 5 days ago
The Mountain Inn at Killington