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Compare 60 Cottages in Woodstock with updated reviews, rates, and availability.

Newly converted 2BR/2BA carriage house!
Newly converted 2BR/2BA carriage house!
10.0 out of 10, Exceptional, (2)
"This property is a hidden gem! Quaint, so cozy, adorably decorated! we absolutely loved everything about it! Wddidnt want to"
Newly converted 2BR/2BA carriage house!
Charming Cavendish Cottage: All-Season Retreat!
Cavendish Vacation Rental | 3BR | 3BA | 1,500 Sq Ft | Stairs Required
Charming Cavendish Cottage: All-Season Retreat!
2.0 star property
10.0 out of 10, Exceptional, (4)
"Such a wonderful and warm home. Other than condiments the kitchen was well stocked with dishes, cups and small appliances. The back screened in porch was a peaceful retreat for morning coffee and devotions and a great place to wind down at night. The owner was very nice and accommodating. The minute we walked in we were in awe of Rosehill Cottage. We will definitely stay here again if we are in the area."
Charming Cavendish Cottage: All-Season Retreat!
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
9.6 out of 10, Exceptional, (9)
"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 Historic Hilltop Cottage with Mount Ascutney View
Cottage on the hill
Cozy Historic Hilltop Cottage with Mount Ascutney View
9.6 out of 10, Exceptional, (74)
"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
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
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
The Carriage House on Main
The Carriage House on Main
9.8 out of 10, Exceptional, (16)
"Clean, quiet lovely property, close to our activities. We enjoyed our stay. Minor note: cooking equipment, utensils and related items are limited. Beds, linens and showers were great!"
The Carriage House on Main
Spruce Moose Cottage | Tiny House on 65 private acres
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
Exterior
Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains
10.0 out of 10, Exceptional, (7)
"Obsessed with this house! It was perfect for 2 couples and our pups for a relaxing fall weekend. Rooms were cozy, updated and super clean. The hot tub, fire pit by the river and big kitchen were highlights. I really appreciated the hospitality of having amenities like spices, coffee filters, shampoo & conditioner, laundry detergent, etc. Would book again!"
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!
Living area
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!
Idyllic Wallingford Retreat - Near Skiing & Hiking
Dining
Idyllic Wallingford Retreat - Near Skiing & Hiking
3.0 star property
Idyllic Wallingford Retreat - Near Skiing & Hiking
Luxury Vermont Vacation Rental: Private Hot Tub!
Dining
Luxury Vermont Vacation Rental: Private Hot Tub!
3.0 star property
Luxury Vermont Vacation Rental: Private Hot Tub!
Wooded Waterfront Grantham Home < 10 Mi to Ski!
Terrace/patio
Wooded Waterfront Grantham Home < 10 Mi to Ski!
3.0 star property
10.0 out of 10, Exceptional, (1)
"Great atmosphere!"
Wooded Waterfront Grantham Home < 10 Mi to Ski!
3-acre Thetford Rental w/ River Access & Upgrades!
Private kitchen
3-acre Thetford Rental w/ River Access & Upgrades!
3.0 star property
3-acre Thetford Rental w/ River Access & Upgrades!
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
Outdoor dining
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
3.0 star property
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
Pet-friendly Claremont Vacation Rental!
Living area
Pet-friendly Claremont Vacation Rental!
3.0 star property
Pet-friendly Claremont Vacation Rental!
Home w/ Sauna - Close to Pico & Killington Mtns!
Living area
Home w/ Sauna - Close to Pico & Killington Mtns!
3.0 star property
Home w/ Sauna - Close to Pico & Killington Mtns!
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
Property grounds
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
3.0 star property
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
Lakefront Paradise Near Okemo & Killington
Property grounds
Lakefront Paradise Near Okemo & Killington
3.0 star property
Lakefront Paradise Near Okemo & Killington
Charming Cavendish Cottage: All-season Retreat!
Exterior
Charming Cavendish Cottage: All-season Retreat!
3.0 star property
10.0 out of 10, Exceptional, (1)
"Excellent property and host. House was comfortable and inviting with all the amenities one could ask for. Beautiful grounds and a pond on property. We will definitely go back. "
Charming Cavendish Cottage: All-season Retreat!
The Mendon Cottage: Charming Home Close to Killington. Discounted Lift Tickets!
The Mendon Cottage: Charming Home Close to Killington. Discounted Lift Tickets!
2.0 star property
10.0 out of 10, Exceptional, (1)
"Property was very comfortable. Check-in was simple, plenty of communication and prompt replies. Would absolutely stay at this property again. "
The Mendon Cottage: Charming Home Close to Killington. Discounted Lift Tickets!
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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Other property types in Woodstock

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
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
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (39)
"Everything was wonderful. Easy in and out. Near to almost everything. Beautiful area. I left my keys by mistake and they were wonderful in getting them back to me. I would stay there again. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor spa tub
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (196)
"A few weeks ago my partner and I stayed at the Hideway Cabin for the fifth year in a row. We made this a yearly tradition of ours. I cannot say enough about the place! The cabin very clean and cozy. The kitchen and bedrooms are stocked with all the necessities. It is located only a few, short minutes from Ludlow's center of town. The hot tub is amazing. I love seeing the stars shining bright at night. Highly recommend!"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
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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