Search Cabin Rentals in Pittsfield

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 48 Cabin Rentals in Pittsfield with updated reviews, rates, and availability.

Cozy Loft for two with Hot Tub & Mtn Views
"This cute and cozy loft was perfect in every way!" JV

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (230)
"Great stay in the mountains. Listing is exactly as advertised. Jeff was great "
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, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Stetson Hollow Cabin by Stetson Brook
Cozy living space with fieldstone fireplace.

Stetson Hollow Cabin by Stetson Brook

9.8 out of 10, Exceptional, (142)
"We loved or stay in the Stetson Hollow cabin! We enjoyed building a cozy fire on a snowy night close to Sugarbush Mountain after a long day of traveling. The cabin was just as expected, clean and comfortable with an easy check in/out process. The host was lovely and easy to communicate with. Would definitely stay again in the future!"
The price is AED 882
AED 1,732 total
includes taxes & fees
2 Mar - 3 Mar
Stetson Hollow Cabin by Stetson Brook
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, (106)
"Beautiful area for short 4 day stay . Cabin was clean and cozy. Well stocked for pretty much anything . Only dislike was the bedroom was in a loft area with narrow steps , and a bit tough to navigate in the middle of the night when the restroom was needed . Loved the quaintness otherwise . "
Classic Vermont Cabin on 2.5 acres Lake Frontage
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, (483)
"We had a great time at the cabin, our second year!! We plan to be back for a third season!!Everything was perfect, the coziness of the cabin was amazing. We were able to watch the Super Bowl again on the huge projection screen!! Hot tub was great after several long days of skiing and snowshoeing!!"
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor spa tub

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (199)
"We loved our stay at this cabin. We came as two couples over Valentines Day Weekend, and went skiing at Okemo (less than 10min away). The cabin has everything you need for a cozy stay and the hot tub at night was delightful. The property manager, Christopher, was also extremely attentive and went above and beyond to help us out. "
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Killington / Mendon CLEAN, 2 bedroom cabin
Living area

Killington / Mendon CLEAN, 2 bedroom cabin

10.0 out of 10, Exceptional, (7)
"This was our first ski trip, and one of our most memorable holiday vacations ever. We were seeking a true mountain cabin experience, and we definitely made the right choice. Prime ski slopes were just minutes away with spectacular views all around the area. Robert was an excellent host and made us feel welcome from check in to check out. He was very attentive to our needs and the cabin was well equipped with everything required to make our trip as comfortable as possible for a family of five. "
Killington / Mendon CLEAN, 2 bedroom cabin
Robert Frost Mountain Cabins
Exterior

Robert Frost Mountain Cabins

3.5 star property
10.0 out of 10, Exceptional, (40)
"We loved how cozy and warm the cabin was, how easy the fireplace was to operate, and how much room we had. The view of sunrise from the back window and our ability to walk out there to enjoy it was a pleasant surprise. We'd love to come back."
The price is AED 871
AED 949 total
includes taxes & fees
23 Feb - 24 Feb
Robert Frost Mountain Cabins
Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape
Tastefully-decorated living room with color accents combining with wood. Wood-burning stove, comfy sofas and a smart TV with streaming services to socialize and relax after a day of adventure.

Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape

10.0 out of 10, Exceptional, (62)
"The cabin was lovely and we really enjoyed staying there. Proximity to the mountain and everything in town was great. "
Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape
Killington Area Escape w/ Deck, Views & Hot Tub!
Stockbridge Vacation Rental | 3BR | 2BA | 2 Stories | Stairs Required

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

9.6 out of 10, Exceptional, (18)
"Was perfect. Property owner very prompt on responses. Definitely reccomend !"
Killington Area Escape w/ Deck, Views & Hot Tub!
Log Cabin Killington Basin-2 min to Mountain Ski Lifts_Yr Round Activities
Scenic View through Pine Tree Branches

Log Cabin Killington Basin-2 min to Mountain Ski Lifts_Yr Round Activities

Log Cabin Killington Basin-2 min to Mountain Ski Lifts_Yr Round Activities
Cabin at Killington: Large Home w/ amenities, views and location close to ski resort. Hot Tub.
Winter exterior view of The Cabin at Killington, our vacation rental home in Killington, Vermont.

Cabin at Killington: Large Home w/ amenities, views and location close to ski resort. Hot Tub.

10.0 out of 10, Exceptional, (12)
"We had a great time at the cabin, perfect for two groups."
Cabin at Killington: Large Home w/ amenities, views and location close to ski resort. Hot Tub.
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
Charming farmhouse, dog friendly, Appalachian trail access

Charming farmhouse, dog friendly, Appalachian trail access

7.2 out of 10, Good, (5)
"Pros: - Very responsive property management - Big house, great Vermont cabin feel - Clean bathrooms and great water pressure - Decently stocked kitchen - Beautiful location/ scenery Cons: - A bit hard to find (google maps gets confused) - We had many flies in kitchen and bedrooms - Heating issues (eventually fixed) - Access issues upon arrival (immediately fixed) - Have to remove your own trash when you leave"
Charming farmhouse, dog friendly, Appalachian trail access
Inviting timber frame cabin in Vermont's Green Mountains
Exterior

Inviting timber frame cabin in Vermont's Green Mountains

10.0 out of 10, Exceptional, (5)
"This is a very special place. Close to Middleburyyetfar away. "
The price is AED 940
AED 1,156 total
includes taxes & fees
25 Feb - 26 Feb
Inviting timber frame cabin in Vermont's Green Mountains
Private pet-friendly cabin in the woods w/ private campfire pit & screened porch
Exterior

Private pet-friendly cabin in the woods w/ private campfire pit & screened porch

10.0 out of 10, Exceptional, (11)
"A piece of heaven hidden in the woods "
The price is AED 940
AED 1,281 total
includes taxes & fees
24 Feb - 25 Feb
Private pet-friendly cabin in the woods w/ private campfire pit & screened porch
Picture-Perfect Vermont Mtn Cabin w/ Hot Tub!
Bridgewater Vacation Rental | 6BR | 3BA | 2,312 Sq Ft | Stairs Required

Picture-Perfect Vermont Mtn Cabin w/ Hot Tub!

9.8 out of 10, Exceptional, (16)
"It was perfect for our family of 12. Close to skiing, Woodstock, Beautiful countryside around our house. "
Picture-Perfect Vermont Mtn Cabin w/ Hot Tub!
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
Exterior

Charming and meticulously cleaned cabin with panoramic view of the Green Mtns

10.0 out of 10, Exceptional, (16)
"It was great, but was about a 10min ride on dirt roads to the cabins. Some might not expect that"
The price is AED 940
AED 1,252 total
includes taxes & fees
23 Feb - 24 Feb
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
Pond View Cabin-Rustic 2 Bedroom-Sleeps 4

Pond View Cabin-Rustic 2 Bedroom-Sleeps 4

Pond View Cabin-Rustic 2 Bedroom-Sleeps 4
Romantic Cabin Pvt Mtn getaway
Exterior

Romantic Cabin Pvt Mtn getaway

10.0 out of 10, Exceptional, (1)
"Peaceful, private cabin. Enjoyed our stay!"
The price is AED 569
AED 856 total
includes taxes & fees
3 Mar - 4 Mar
Romantic Cabin Pvt Mtn getaway
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.
Don't see what you're looking for?
See all available properties in Pittsfield
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Pittsfield

Cozy Loft for two with Hot Tub & Mtn Views
"This cute and cozy loft was perfect in every way!" JV

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (230)
"Great stay in the mountains. Listing is exactly as advertised. Jeff was great "
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, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

8.4 out of 10, Very Good, (27)
"It’s a great location, and the unit is well updated, but being able to lock it while you’re away skiing the whole day is pretty important. When I reached out to the property manager about this, and also a disgusting towel left near the toilet on arrival, the response was basically oh no! That’s awful! We’ve told someone.. aaaand nothing ever happened about either thing. These issues weren’t insurmountable, but doing nothing at all about them just left a terrible impression."
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
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.