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.
Kitchen
Washer
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Leicester VT
$195 nightly
The price is $218 total per night
$218 total
Oct 13 - Oct 14
Total with taxes and fees
Guests of this cottage enjoy access to ski-in/ski-out access, laundry facilities, and a garden.
Kitchen
Washer
Cozy Historic Hilltop Cottage with Mount Ascutney View

Cozy Historic Hilltop Cottage with Mount Ascutney View

West Windsor VT
Guests staying at this cottage have access to a garden and barbecue grills.
Kitchen
Free WiFi
Cozy Cabin Retreat

Cozy Cabin Retreat

Roxbury VT
$204 nightly
The price is $228 total per night
$228 total
Oct 21 - Oct 22
Total with taxes and fees
At this cottage, guests have access to a garden.
Kitchen
Free WiFi
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.
Kitchen
Washer
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 a garden. This smoke-free cottage also has barbecue grills.
Hot Tub
Kitchen
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

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

Mendon VT
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Kitchen
Washer
Ski-in 4 bedroom, 3.5 baths, pool, hot tub, and mountain views.

Ski-in 4 bedroom, 3.5 baths, pool, hot tub, and mountain views.

Killington VT
This cottage features ski-in/ski-out access, an indoor pool, and a gym. Other amenities at this ski cottage include a sauna, a hot tub, and an arcade/game room.
Pool
Hot Tub
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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

    Comfort Inn Rutland - Killington

    Comfort Inn Rutland - Killington

    19 Allen St Rutland VT
    $121 nightly
    The price is $133 total per night from Oct 29 to Oct 30
    $133 total
    Oct 29 - Oct 30
    Total with taxes and fees
    8/10 Very Good! (1,009 reviews)
    The Mountain Inn at Killington

    The Mountain Inn at Killington

    47 Old Mill Rd Killington VT
    $156 nightly
    The price is $172 total per night from Oct 19 to Oct 20
    $172 total
    Oct 19 - Oct 20
    Total with taxes and fees
    9.2/10 Wonderful! (1,002 reviews)
    Align Inn Vermont

    Align Inn Vermont

    5817 Woodstock Rd Quechee VT
    $206 nightly
    The price is $226 total per night from Oct 21 to Oct 22
    $226 total
    Oct 21 - Oct 22
    Total with taxes and fees
    9.4/10 Exceptional! (1,378 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
71 Cottages
Lowest Price
$133
Highest Price
$228
Popular accommodation
Norwich Village cottage built 2026 2 miles to Dartmouth+King Arthur Baking Co., Woodstock Village Carriage House, Pristine Custom Cottage, Grand Piano, Massage Studio on Site, Cozy Historic Hilltop Cottage with Mount Ascutney View, 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, The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland., Ski-in 4 bedroom, 3.5 baths, pool, hot tub, and mountain views.

More to Explore