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Featured Cottages in Stockbridge

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

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

Stockbridge
Located in Stockbridge, this cottage is within a 15-minute drive of Green Mountain National Forest and Silver Lake State Park.
Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

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

Woodstock
When you stay at this cottage in Woodstock, you'll be on the waterfront, within a 5-minute drive of Taftsville Covered Bridge and Green Mountain Rock Climbing ...
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Leicester
The price is AU$317 per night from 30 Dec to 31 Dec
AU$317
includes taxes & fees
30 Dec - 31 Dec
With a stay at this cottage, you'll be centrally located in Brandon, within a 10-minute drive of Lake Dunmore and Brandon Museum.
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
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Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

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

Ludlow
With a stay at this cottage in Ludlow, you'll be on the beach, within a 10-minute drive of Okemo Mountain Resort and Lake Rescue.
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Cozy Cabin Retreat

Cozy Cabin Retreat

Roxbury
Located in Randolph, this cottage is in the mountains, a 1-minute drive from Mad River Valley and 9 minutes from Allis State Park.
Cozy Cabin Retreat
Cozy Historic Hilltop Cottage with Mount Ascutney View

Cozy Historic Hilltop Cottage with Mount Ascutney View

Windsor
With a stay at this cottage in Windsor, you'll be within a 15-minute drive of Mt Ascutney State Park and Brownsville Trail.
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

Hartland
This cottage is 5.8 mi (9.3 km) from Woodstock Town Hall Theatre and 5.8 mi (9.4 km) from Red Wagon Toy Company.
Spruce Moose Cottage | Tiny House on 65 private acres
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
When you stay at this cottage in Reading, you'll be on a river and 11 minutes by car from Mt Ascutney State Park.
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
Lovely Brookfield Home w/ Private Deck & Views

Lovely Brookfield Home w/ Private Deck & Views

3 out of 5
Brookfield
With a stay at this cottage in Brookfield, you'll be 26.9 mi (43.3 km) from Sugarbush Ski Resort and 5.1 mi (8.3 km) from Mad River Valley.
Lovely Brookfield Home w/ Private Deck & Views
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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.

Stockbridge Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Stockbridge will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Stockbridge definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Stockbridge, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Stockbridge Cottages essential information

Accommodation
42 Cottages
Lowest Price
AU$238
Highest Price
AU$346
Popular accommodation
Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains, Cozy 1850s home on the riverfront with mountain & river views - dog-friendly, Pristine Custom Cottage, Grand Piano, Massage Studio on Site, Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit, Cozy Cabin Retreat, Cozy Historic Hilltop Cottage with Mount Ascutney View, Spruce Moose Cottage | Tiny House on 65 private acres, Cozy cottage on the river, minutes from skiing, horse events, and so much more!, Lovely Brookfield Home w/ Private Deck & Views

Top trending hotels in Stockbridge

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd, Killington, VT
Fully refundableReserve now, pay when you stay
The price is AU$346 per night from 14 Jan to 15 Jan
AU$346
includes taxes & fees
14 Jan - 15 Jan 2025
With a stay at Killington Mountain Lodge, Tapestry Collection by Hilton in Killington, you'll be next to a golf course, just steps from Killington Resort and ...
Killington Mountain Lodge, Tapestry Collection by Hilton
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is AU$268 per night from 16 Jan to 17 Jan
AU$268
includes taxes & fees
16 Jan - 17 Jan 2025
With a stay at Comfort Inn Rutland - Killington in Rutland, you'll be 0.6 mi (1 km) from Rutland Regional Medical Center and 9.8 mi (15.7 km) from Pico Mountain ...
Comfort Inn Rutland - Killington
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr, Killington, VT
The price is AU$282 per night from 8 Jan to 9 Jan
AU$282
includes taxes & fees
8 Jan - 9 Jan 2025
Located in Killington, North Star Lodge and Resort is in the mountains, a 3-minute drive from Killington Resort and 5 minutes from Killington Golf Course.
North Star Lodge and Resort
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Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
401 US-7, Located At The Junction Of Us 4 And Us 7, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is AU$238 per night from 25 Dec to 26 Dec
AU$238
includes taxes & fees
25 Dec - 26 Dec
When you stay at Days Inn by Wyndham Rutland/Killington Area in Rutland, you'll be near ski lifts, within a 5-minute drive of Vermont State Fairgrounds and Rutland ...
Days Inn by Wyndham Rutland/Killington Area
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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.

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^Subject to availability and chosen travel dates.