Search Cottages in Stockbridge

  • 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
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month

Compare 41 Cottages in Stockbridge with updated reviews, rates, and availability.

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

9.2 out of 10, Wonderful, (15)
"We loved the cabin and its proximity to the town of Woodstock. Nice to come home at the end of the day. The only issue is the bedrooms are upstairs and the bathroom is downstairs….but we managed. Overall a great stay. "
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

10.0 out of 10, Exceptional, (50)
"This was my first experience with Vrbo. It was wonderful. Checking in and out of the property was simple! My fiancé and I were seeking a Christmas getaway in Vermont. We certainly found it! The property is in close distance to Brandon and Middlebury. Both towns have lots of dining options and shopping. We visited a brewery and winery. Our cottage in Leicester was pristine. Our host, David. was accommodating and friendly. The cottage is well built and you can see how much work David has put into...
The price is SAR 488
SAR 761 total
includes taxes & fees
22 Jan - 23 Jan
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

9.6 out of 10, Exceptional, (10)
"This lake house is absolutely everything you would expect from a five star rated home. It is a newly renovated lake front home. The house is located about 3 miles north of Ludlow. The property was clean and well maintained. We visited on Columbus Day weekend for our daughter’s wedding. We will return some day in the summer to enjoy the lake. I would recommend this property to my family and friends. Thank you for sharing your home with us during this special time for our family. "
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

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."
The price is SAR 488
SAR 861 total
includes taxes & fees
20 Jan - 21 Jan
Cozy Cabin Retreat

Cozy Historic Hilltop Cottage with Mount Ascutney View

9.6 out of 10, Exceptional, (75)
"This house is exactly as described. It is in a very attractive location with good views and is very private. The house is much larger inside than it appears from the photos but still very cozy and is well equipped. It was spotlessly clean."
Cozy Historic Hilltop Cottage with Mount Ascutney View

Spruce Moose Cottage | Tiny House on 65 private acres

Spruce Moose Cottage | Tiny House on 65 private acres

Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains

10.0 out of 10, Exceptional, (8)
"We spent Christmas 2024 at this lovely ski house. We’d return again! How’s an amazing. Seamless communication and great location !"
Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains

Cozy cottage on the river, minutes from skiing, horse events, and so much more!

10.0 out of 10, Exceptional, (7)
"We loved our stay at the Dark Horse Cottage. It was close to everything we wanted to do. We loved being near the little creek. They thought of everything for amenities. It was perfect for what we needed. "
Cozy cottage on the river, minutes from skiing, horse events, and so much more!

Lovely Brookfield Home w/ Private Deck & Views

3.0 star property
10.0 out of 10, Exceptional, (1)
" Lovely home, beautifully furnished "
Lovely Brookfield Home w/ Private Deck & Views

Inviting A-frame Cabin w/ Saltwater Hot Tub!

3.0 star property
Inviting A-frame Cabin w/ Saltwater Hot Tub!

Historic Vermont Ski House w/ Mountain Views!

3.0 star property
Historic Vermont Ski House w/ Mountain Views!

Rustic Roxbury Ski Farmhouse With Trails!

3.0 star property
Rustic Roxbury Ski Farmhouse With Trails!

Picture-perfect Vermont Mtn Cabin w/ Hot Tub!

3.0 star property
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!

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

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

Pet-friendly Roxbury Farmhouse on 350 Acres!

3.0 star property
Pet-friendly Roxbury Farmhouse on 350 Acres!

Lakefront Paradise Near Okemo & Killington

3.0 star property
Lakefront Paradise Near Okemo & Killington

The Mendon Cottage: Charming Home Close to Killington. Discounted Lift Tickets!

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great location close to Killington. Accurate listing. Nothing fancy but all the necessities available. Was clean and comfortable. Driveway was plowed early for easy access in/out."
The Mendon Cottage: Charming Home Close to Killington. Discounted Lift Tickets!

Vermont Retreat - 8 Mi to Killington Ski Area

3.0 star property
Vermont Retreat - 8 Mi to Killington Ski Area

Duplex Unit, 2 Mi to Chittenden Reservoir!

3.0 star property
Duplex Unit, 2 Mi to Chittenden Reservoir!

Remote Escape: Vermont Cabin w/ Mountaintop Views!

2.0 star property
Remote Escape: Vermont Cabin w/ Mountaintop Views!
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 Stockbridge
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Stockbridge

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (226)
"Such a cute, quaint space. Would love to come back in the summer to take full advantage of the area. Came in the winter time so we could not use the deck and fire pit. Definitely a great feature for extra space to eat on the deck during warmer time. Pull up coffee table inside is convenient for eating during Winter, since there is no other dining area. Winter time is great if you ski/snowboard, close to ski areas. We went into Rochester for lunch one day, and was a nice small "downtown". The...
Cozy Loft for two with Hot Tub

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

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

10.0 out of 10, Exceptional, (477)
"It was great! Nice spot, great hottub and close to ski slopes"
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
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.

Frequently asked questions

Why book your cottage in Stockbridge with Expedia?
We think that vacays should be stress-free, so if you’re in search of cottages in Stockbridge at an affordable price, Expedia has got you covered. Keep costs down and go for a low-cost option far from the hustle and bustle, or splurge on a 5-star cottage to spoil your favorite people.
How can I find cheap cottages in Stockbridge?
With Expedia’s handy filter tool, booking cheap cottages in Stockbridge is easy. To find accommodations that’ll make your wallet happy, narrow your search by star rating, budget and amenities.