Search Cabin Rentals in Stockbridge

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Stockbridge cabin rentals

Exterior
Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups

Cabin in Stockbridge

Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups
8.0 out of 10, Very Good, (1)
"Would like to have had a tv in all the bedrooms. The back yard needed mowed. Other than that it was a good stay. Nice place"
United States
Troy H.
The price is AED 1,139
AED 3,343 total
includes taxes & fees
11 Dec - 12 Dec
Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups
Exterior
Secluded retreat in the trees

Cabin in Roxbury

Secluded retreat in the trees
10.0 out of 10, Exceptional, (36)
"Absolutely beautiful! So pleased with everything about our stay!"
United States
Gwen B.
The price is AED 463
AED 864 total
includes taxes & fees
14 Dec - 15 Dec
Secluded retreat in the trees
Exterior
Treehouse at Wise Pines- NoBo

Cabin in Woodstock

Treehouse at Wise Pines- NoBo
9.8 out of 10, Exceptional, (13)
"Unique settings. Loved the accommodations "
United States
Gabriela
The price is AED 551
AED 687 total
includes taxes & fees
11 Dec - 12 Dec
Treehouse at Wise Pines- NoBo
Exterior
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Cabin in Cavendish

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
2.0 star property
10.0 out of 10, Exceptional, (10)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
The price is AED 826
AED 1,366 total
includes taxes & fees
16 Dec - 17 Dec
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Property grounds
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Cabin in Rutland

Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
2.5 star property
9.4 out of 10, Exceptional, (3)
"Absolutely adored our stay! The cabin was cozy and had everything we could need and the hot tub was a huge plus after a long day of snowboarding. Would definitely come back!"
United States
Erin M.
The price is AED 551
AED 708 total
includes taxes & fees
12 Dec - 13 Dec
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
Exterior
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Cabin in Sharon

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
10.0 out of 10, Exceptional, (3)
"Very welcoming, awesome weekend getaway."
United States
Zachary B.
The price is AED 393
AED 966 total
includes taxes & fees
15 Dec - 16 Dec
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Exterior
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Cabin in Killington

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
2.0 star property
10.0 out of 10, Exceptional, (11)
"The cabin was cozy. It was set up nicely and had all the necessities we needed."
United States
Philip
The price is AED 586
AED 1,845 total
includes taxes & fees
11 Dec - 12 Dec
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Exterior
Robert Frost Mountain Cabins

Cabin in Ripton

Robert Frost Mountain Cabins
3.5 star property
10.0 out of 10, Exceptional, (40)
"Ammazing,would go again!"
United States
Joseph
The price is AED 1,004
AED 1,095 total
includes taxes & fees
4 Jan - 5 January 2026
Robert Frost Mountain Cabins
Exterior
Stetson Hollow Cabin by Stetson Brook

Cabin in Warren

Stetson Hollow Cabin by Stetson Brook
9.8 out of 10, Exceptional, (159)
"Great location and a great price. Perfect for 2-4 people who just want to get away to the peace of Vermont."
United States
James N.
Stetson Hollow Cabin by Stetson Brook
Exterior
Adorable cabin with screened porch and private fire pit

Cabin in Ripton

Adorable cabin with screened porch and private fire pit
10.0 out of 10, Exceptional, (5)
"Wonderful place to stay tucked away in the woods. The owners are extremely thoughtful and personable. Can’t wait to go back. "
United States
Sorin
The price is AED 940
AED 1,273 total
includes taxes & fees
11 Dec - 12 Dec
Adorable cabin with screened porch and private fire pit
Exterior
Killington Cabin - Left Unit: Great for families, Cozy, Close to Mountain. Hot Tub. Wood Stove.

Cabin in Killington

Killington Cabin - Left Unit: Great for families, Cozy, Close to Mountain. Hot Tub. Wood Stove.
9.6 out of 10, Exceptional, (19)
"Nice place with plenty of beds, clean and comfortable!"
United States
David L.
The price is AED 1,248
AED 2,676 total
includes taxes & fees
11 Dec - 12 Dec
Killington Cabin - Left Unit: Great for families, Cozy, Close to Mountain. Hot Tub. Wood Stove.
Exterior
Cozy and pristine timberframe cabin

Cabin in Ripton

Cozy and pristine timberframe cabin
10.0 out of 10, Exceptional, (4)
"It is a gorgeous property with lots of fun amenities...perfect for a winter getaway"
United States
Karen H.
The price is AED 940
AED 1,273 total
includes taxes & fees
11 Dec - 12 Dec
Cozy and pristine timberframe cabin
Exterior
Ludlow Ski Cabin 2 Mi to Ski Parking

Cabin in Ludlow

Ludlow Ski Cabin 2 Mi to Ski Parking
2.0 star property
The price is AED 599
AED 1,374 total
includes taxes & fees
18 Dec - 19 Dec
Ludlow Ski Cabin 2 Mi to Ski Parking
Exterior
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around

Cabin in Hancock

Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
10.0 out of 10, Exceptional, (1)
"This place was great, and perfect for our night’s stay. The hot tub was clean and in excellent condition and we loved having that amenity! The owner was easy to get in touch with and replied to my questions very quickly. We’d love to visit again!"
United States
Stephanie F.
The price is AED 592
AED 1,432 total
includes taxes & fees
20 Dec - 21 Dec
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Exterior
All-Season Lake Pauline Retreat, 2 mi to Okemo

Cabin in Ludlow

All-Season Lake Pauline Retreat, 2 mi to Okemo
9.0 out of 10, Wonderful, (2)
"House was very nice. Very close to Okemo. Had everything we needed on a sweet lake with a sugar shack directly across. Layout is a little funky but worked just fine. Beds are very comfy. "
United States
Kristen M.
The price is AED 1,307
AED 2,370 total
includes taxes & fees
5 Jan - 6 January 2026
All-Season Lake Pauline Retreat, 2 mi to Okemo
Exterior
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns

Cabin in Ripton

Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
10.0 out of 10, Exceptional, (17)
"Beautiful place. Lots to do around the cabin and in the area. The hosts are very helpful. The cabin has everything you could want for a great stay. "
United States
Susan
The price is AED 940
AED 1,273 total
includes taxes & fees
16 Dec - 17 Dec
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
Exterior
Treehouse at Wise Pines- SoBo

Cabin in Woodstock

Treehouse at Wise Pines- SoBo
9.8 out of 10, Exceptional, (24)
"What a unique experience staying in a literal tree house. The bathroom shared with the other tree house was so wonderfully built as is the barn that it resides in. I only stayed one night and wished I stayed multiple nights. I will definitely consider staying here again for future MTB trips in the area! "
United States
Taku S.
The price is AED 551
AED 687 total
includes taxes & fees
16 Dec - 17 Dec
Treehouse at Wise Pines- SoBo
Exterior
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest

Cabin in Ripton

Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
9.4 out of 10, Exceptional, (12)
"Our group booked this place for a ski trip to sugarbush. A remote area, but the cabin was very cool and our host were the best. The warm cinnamon twists in the morning were a big hit and the hot tub was perfect after a day of skiing. Would definitely look into booking this in the summer/fall. "
United States
John H.
The price is AED 940
AED 1,273 total
includes taxes & fees
14 Dec - 15 Dec
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
Exterior
Emrose Luxury Cabins 13

Cabin in Brandon

Emrose Luxury Cabins 13
The price is AED 834
AED 1,079 total
includes taxes & fees
20 Dec - 21 Dec
Emrose Luxury Cabins 13
Exterior
Roaring Bear Cabin: Secluded Killington Retreat with Hot Tub and Fire Pit

Cabin in Killington

Roaring Bear Cabin: Secluded Killington Retreat with Hot Tub and Fire Pit
2.0 star property
The price is AED 893
AED 2,612 total
includes taxes & fees
11 Dec - 12 Dec
Roaring Bear Cabin: Secluded Killington Retreat with Hot Tub and Fire Pit
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Stockbridge Hotel Reviews

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

10/10 Excellent
"We stopped at this hotel on our way up to Stowe Mountain traveling from NJ. The room was affordable, modern, & clean. Our hotel room was a pleasant surprise. We had a full size fridge, microwave, oven, & kitchen in there. We stayed in a hearing impaired room that had a very spacious bathroom. We didn’t notice a lot of food options other than a McDonalds and convenience store about half a mile away. The lobby had a lot of amenities like snacks and other items you may have forgot to pack but were on the pricey side (ex. A bottle of Diet Coke was $4). We would definitely stay again."
Ellen M 1-night trip
Posted 3 days ago
My Place Hotel-Randolph VT