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29 Aug - 31 Aug
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19 Sep - 21 Sep
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Cabin Rentals in Pittsfield

Our top choices for Pittsfield cabin rentals

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, (253)
"We had the most amazing week from check in to check out! We cant wait to come back."
Cozy Loft for two with Hot Tub & Mtn Views
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, (47)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
TV, fireplace, DVD player, books

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

10.0 out of 10, Exceptional, (505)
"Our stay at the Vermont Cabin "Romantic Retreat" was amazing. Owner was very communicative and made our stay stress free. Even though it's listed as a romantic retreat, it was great for the family too. The cabin was well stocked with everything we needed during our stay and the hottub was definitely a hit. We cant wait for our next stay."
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Classic Vermont Cabin on 2.5 acres Lake Frontage
Property grounds

Classic Vermont Cabin on 2.5 acres Lake Frontage

9.8 out of 10, Exceptional, (110)
"Very quiet, well appointed cottage! So peaceful, beautiful scenery and VERY accommodating host!"
Classic Vermont Cabin on 2.5 acres Lake Frontage
Stetson Hollow Cabin by Stetson Brook
Fireplace, books

Stetson Hollow Cabin by Stetson Brook

9.8 out of 10, Exceptional, (148)
"Perfect retreat inside a charming cabin for a ski getaway. Enjoy memorable family moments. "
The price is SAR 901
SAR 1,723 total
includes taxes & fees
10 Sep - 11 Sep
Stetson Hollow Cabin by Stetson Brook
Secluded retreat in the trees
Exterior

Secluded retreat in the trees

10.0 out of 10, Exceptional, (25)
"The place was great ,it fit into our budget and the owners were more than helpful."
The price is SAR 524
SAR 956 total
includes taxes & fees
3 Sep - 4 Sep
Secluded retreat in the trees
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor dining

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (215)
"Cozy and scenic property here with more than enough space, great spot with a dog, to go hiking, or just relax."
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Alpine Village Chalet
Interior

Alpine Village Chalet

2.0 star property
10.0 out of 10, Exceptional, (7)
"Our stay at this cozy cabin was just what we needed. Ample room, comfortable beds, clean linens and a superb property in a quiet neighbourhood, our kids enjoyed the yard full of snow and their bunking “nook” upstairs. We loved the time together and enjoyed the amenities offered. The owners were always quick to respond. We recommend for a quiet weekend away. "
Alpine Village Chalet
Vineyard Cabin
Property grounds

Vineyard Cabin

10.0 out of 10, Exceptional, (1)
"The cabin was quaint and perfect for what we were looking for. We were close to town, but felt way more isolated. The cabin was off grid, but had running water and electricity. We were comfortable and very happy with our stay. It was beautiful and wildlife was abundant. The hosts were attentive, but not intrusive. We will definitely be back."
Vineyard Cabin
NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
Microwave, oven, stovetop, dishwasher

NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!

10.0 out of 10, Exceptional, (1)
"Overall a great place. Beautiful location, tucked away from everything but still jist a few minutes from Killington base. Very clean and well-kept, everything we needed was there.Host communicated regularly and responded quickly.If you stay in winter, 4WD might be needed to get in and out without issue. And for the shorter route to and from Killington - its a very steep road.Beautiful interior, needs some age to feel warmer and homey, but good seating and open family room is great for...
The price is SAR 1,501
SAR 3,028 total
includes taxes & fees
27 Aug - 28 Aug
NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
SPRING IN THE GREEN MOUNTAINS/PET FRIENDLY-WOOF
Fridge, microwave, oven, stovetop

SPRING IN THE GREEN MOUNTAINS/PET FRIENDLY-WOOF

10.0 out of 10, Exceptional, (89)
"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 SAR 1,058
SAR 1,154 total
includes taxes & fees
1 Sep - 2 Sep
Robert Frost Mountain Cabins
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 SAR 553
SAR 1,827 total
includes taxes & fees
24 Aug - 25 Aug
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Charming farmhouse, dog friendly, Appalachian trail access
Fridge, microwave, oven, stovetop

Charming farmhouse, dog friendly, Appalachian trail access

7.2 out of 10, Good, (5)
"A lovely "get-away" in beautiful Vermont."
Charming farmhouse, dog friendly, Appalachian trail access
Killington / Mendon CLEAN, 1 bedroom cabin
Fridge, microwave, oven, stovetop

Killington / Mendon CLEAN, 1 bedroom cabin

9.8 out of 10, Exceptional, (20)
"Clean and close to the mountain"
Killington / Mendon CLEAN, 1 bedroom cabin
Cozy Brookside Cabin with Hot Tub | Woodstock VT
Outdoor spa tub

Cozy Brookside Cabin with Hot Tub | Woodstock VT

10.0 out of 10, Exceptional, (1)
"The property is very clean and well maintained. The hosts have put a lot of thought into the stocked amenities not only for comfort and convenience but also for quality. We enjoyed the outdoor area, the deep soak bathtub, cooking in the kitchen, and doing a puzzle. Will definitely stay again."
Cozy Brookside Cabin with Hot Tub | Woodstock VT
The Cabin that brings people together
Smart TV, fireplace, video games, DVD player

The Cabin that brings people together

9.6 out of 10, Exceptional, (80)
"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
Picture-Perfect Vermont Mtn Cabin w/ Hot Tub!
Fridge, microwave, stovetop, dishwasher

Picture-Perfect Vermont Mtn Cabin w/ Hot Tub!

9.6 out of 10, Exceptional, (17)
"A great family vacation! we went the week of Thanksgiving and it snowed that day, which made it perfect. Paul the hostess made sure that the driveway was plowed and a path to the hot tub and he was easy to get a hold. Cabin was perfect for our family."
Picture-Perfect Vermont Mtn Cabin w/ Hot Tub!
Killington Area Escape w/ Deck, Views & Hot Tub!
Exterior

Killington Area Escape w/ Deck, Views & Hot Tub!

9.6 out of 10, Exceptional, (21)
"Place is amazing the hot tub could use a cleaning but other than that it's perfect for us"
Killington Area Escape w/ Deck, Views & Hot Tub!
Robinson Cabin 3 Bedroom Cabin by RedAwning
Cabin, 3 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster

Robinson Cabin 3 Bedroom Cabin by RedAwning

3.0 star property
Robinson Cabin 3 Bedroom Cabin by RedAwning
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
"The hotel is very nice, very friendly, beautiful views specially from the room with balcony. Game room is awesome and the breakfast was delicious. Will come back again. "
DANIEL 2-night trip
Posted 14 hours ago
The Mountain Inn at Killington