Compare Stockbridge Cottage Rentals

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Featured Cottages in Stockbridge

Norwich Village cottage built 2026 2 miles to Dartmouth+King Arthur Baking Co.

Norwich Village cottage built 2026 2 miles to Dartmouth+King Arthur Baking Co.

Norwich VT
At this cottage, guests have access to a garden.
Kitchen
Free WiFi
Woodstock Village Carriage House

Woodstock Village Carriage House

Woodstock VT
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
Cozy Historic Hilltop Cottage with Mount Ascutney View

Cozy Historic Hilltop Cottage with Mount Ascutney View

West Windsor VT
Guests staying at this cottage can enjoy a gym, barbecue grills, and a garden.
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Leicester VT
$186 nightly
The price is $208 total per night
$208 total
Aug 2 - Aug 3
Total with taxes and fees
Guests of this cottage enjoy access to ski-in/ski-out access, laundry facilities, and a garden.
Kitchen
Washer
Beautiful Timberframe Cottage Nestled in Kumari of the Woods

Beautiful Timberframe Cottage Nestled in Kumari of the Woods

Strafford VT
This cottage is a smoke-free cottage.
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

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

Mendon VT
$390 nightly
The price is $441 total per night
$441 total
Jul 7 - Jul 8
Total with taxes and fees
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Cozy Cabin Retreat

Cozy Cabin Retreat

Roxbury VT
At this cottage, guests have access to a garden.
Cozy cottage on the river, minutes from skiing, horse events, and so much more!

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

Reading VT
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

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

Ludlow VT
This cottage features a hot tub and barbecue grills. This smoke-free cottage also has a garden.
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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.

Hotel Options in Stockbridge

    Align Inn Vermont

    Align Inn Vermont

    5817 Woodstock Rd Quechee VT
    $131 nightly
    The price is $144 total per night from Jul 13 to Jul 14
    $144 total
    Jul 13 - Jul 14
    Total with taxes and fees
    9.4/10 Exceptional! (1,236 reviews)
    Killington Mountain Lodge, Tapestry Collection by Hilton

    Killington Mountain Lodge, Tapestry Collection by Hilton

    2617 Killington Rd Killington VT
    $139 nightly
    The price is $152 total per night from Jul 19 to Jul 20
    $152 total
    Jul 19 - Jul 20
    Total with taxes and fees
    7.4/10 Good! (1,005 reviews)
    Woodstock Inn & Resort

    Woodstock Inn & Resort

    Fourteen The Green Woodstock VT
    $489 nightly
    The price is $538 total per night from Jul 7 to Jul 8
    $538 total
    Jul 7 - Jul 8
    Total with taxes and fees
    9.4/10 Exceptional! (589 reviews)

Cottages

Book a cottage in Stockbridge
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Stockbridge. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Stockbridge better.

Cottage apartments in Stockbridge range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Stockbridge
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Stockbridge and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Stockbridge cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Stockbridge. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Stockbridge Cottages essential information

Accommodation
64 Cottages
Lowest Price
$144
Highest Price
$538
Popular accommodation
Norwich Village cottage built 2026 2 miles to Dartmouth+King Arthur Baking Co., Woodstock Village Carriage House, Cozy Historic Hilltop Cottage with Mount Ascutney View, Pristine Custom Cottage, Grand Piano, Massage Studio on Site, Beautiful Timberframe Cottage Nestled in Kumari of the Woods, The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland., Cozy Cabin Retreat, Cozy cottage on the river, minutes from skiing, horse events, and so much more!, Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

More to Explore