Search Stockbridge Cottage Rentals from CA $124

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Browse Select Stockbridge Cottages

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

10.0 out of 10, Exceptional, (56)
"It was such a lovely stay. Everything was super tidy, clean, comfortable and cozy. We especially loved reading about the story of the build. Would absolutely recommend! "
The price is CA $124
CA $215 total
includes taxes & fees
Aug 11 - Aug 12
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Woodstock Village Carriage House

9.6 out of 10, Exceptional, (92)
"Location was great!!"
Woodstock Village Carriage House

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

2.0 star property
10.0 out of 10, Exceptional, (4)
"Nice time, great location"
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

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

9.8 out of 10, Exceptional, (16)
"We loved the house and especially the location. The views are beautiful and the proximity to town, the mountain and parks make it a fantastic spot to stay."
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

The Paw House Inn & Country Cottages

The Paw House Inn & Country Cottages

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

10.0 out of 10, Exceptional, (7)
"very good cozy location. enjoyed the privacy during our stay."
Cozy cottage on the river, minutes from skiing, horse events, and so much more!

Cozy Cabin Retreat

10.0 out of 10, Exceptional, (29)
"This cabin was perfect! Clean and lovely - loved opening the back door and hearing the brook go by in the back yard. The hosts were super kind and considerate. Loved meeting their puppies! Would go back in a heartbeat - super convenient to the highway and easy to get to and from."
Cozy Cabin Retreat

Cozy Historic Hilltop Cottage with Mount Ascutney View

9.6 out of 10, Exceptional, (78)
"Had a great stay at the old school house. Location was perfect for what we needed. Place was super clean and well appointed. Would love to come back again."
Cozy Historic Hilltop Cottage with Mount Ascutney View

Picture-perfect Vermont Mtn Cabin w/ Hot Tub!

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

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

Rustic Roxbury Ski Farmhouse With Trails!

3.0 star property
Rustic Roxbury Ski Farmhouse With Trails!

Pet-friendly Roxbury Farmhouse on 350 Acres!

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

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

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

Inviting A-frame Cabin w/ Saltwater Hot Tub!

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

Spruce Moose Cottage | Tiny House on 65 private acres

Spruce Moose Cottage | Tiny House on 65 private acres

Lakefront Paradise Near Okemo & Killington

3.0 star property
Lakefront Paradise Near Okemo & Killington

Rustic Mountain View Cottage

Rustic Mountain View Cottage

Swim, Ski & Sip: Lakefront Retreat in Plymouth

3.0 star property
Swim, Ski & Sip: Lakefront Retreat in Plymouth

Peaceful Cavendish Retreat w/ Hot Tub & Fireplace!

3.0 star property
Peaceful Cavendish Retreat w/ Hot Tub & Fireplace!

Cozy Okemo Cabin: Steps to Lake, 2 Mi to Slopes!

3.0 star property
Cozy Okemo Cabin: Steps to Lake, 2 Mi to Slopes!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Stockbridge Hotel Reviews