Book Windsor County, VT Cottages
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Top cities with Cottages to explore in Windsor County
Woodstock
Cottages
Top Cottages in Windsor County
Addie's Place: A Quiet and Quirky Guesthouse
Hartford VT
$229 nightly
The price is $259 total per night
$259 total
Oct 28 - Oct 29
Total with taxes and fees
This cottage includes a garden and barbecue grills.
Pet friendly
Free WiFi
Norwich Village cottage built 2026 2 miles to Dartmouth+King Arthur Baking Co.
Norwich VT
A garden is available at this cottage.
Kitchen
Free WiFi
Woodstock Village Carriage House
Woodstock VT
This cottage includes a garden and laundry facilities.
Kitchen
Washer
Cozy Historic Hilltop Cottage with Mount Ascutney View
West Windsor VT
This cottage includes a garden and barbecue grills.
Kitchen
Free WiFi
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
Reading VT
This cottage featured laundry facilities and barbecue grills.
Kitchen
Washer
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Ludlow VT
A hot tub is featured at this cottage, along with a garden and barbecue grills.
Hot Tub
Kitchen
Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish VT
$484 nightly
The price is $542 total per night
$542 total
Nov 2 - Nov 3
Total with taxes and fees
This cottage features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
Ludlow VT
$271 nightly
The price is $298 total per night
$298 total
Oct 15 - Oct 16
Total with taxes and fees
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. A computer station and barbecue grills are also provided.
Kitchen
Washer
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Chester VT
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.
Kitchen
Washer
Family-friendly Ludlow Cabin on Lake Pauline!
Ludlow VT
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.
Kitchen
Dryer
Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!
Ludlow VT
Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.
Kitchen
Washer
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.
Top Cottages in Windsor County
Addie's Place: A Quiet and Quirky Guesthouse
Hartford VT
$229 nightly
The price is $259 total per night
$259 total
Oct 28 - Oct 29
Total with taxes and fees
This cottage includes a garden and barbecue grills.
Pet friendly
Free WiFi
Norwich Village cottage built 2026 2 miles to Dartmouth+King Arthur Baking Co.
Norwich VT
A garden is available at this cottage.
Kitchen
Free WiFi
Woodstock Village Carriage House
Woodstock VT
This cottage includes a garden and laundry facilities.
Kitchen
Washer
Cozy Historic Hilltop Cottage with Mount Ascutney View
West Windsor VT
This cottage includes a garden and barbecue grills.
Kitchen
Free WiFi
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
Reading VT
This cottage featured laundry facilities and barbecue grills.
Kitchen
Washer
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Ludlow VT
A hot tub is featured at this cottage, along with a garden and barbecue grills.
Hot Tub
Kitchen
Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish VT
$484 nightly
The price is $542 total per night
$542 total
Nov 2 - Nov 3
Total with taxes and fees
This cottage features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
Ludlow VT
$271 nightly
The price is $298 total per night
$298 total
Oct 15 - Oct 16
Total with taxes and fees
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. A computer station and barbecue grills are also provided.
Kitchen
Washer
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Chester VT
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.
Kitchen
Washer
Family-friendly Ludlow Cabin on Lake Pauline!
Ludlow VT
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.
Kitchen
Dryer
Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!
Ludlow VT
Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.
Kitchen
Washer
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.
Top hotels in Windsor County
The Jackson
43 Senior Lane Woodstock VT
$150 nightly
The price is $165 total per night from Nov 3 to Nov 4
$165 total
Nov 3 - Nov 4
Total with taxes and fees
9.6/10 Exceptional! (328 reviews)
Windsor County Cottages essential information
Accommodation | 55 Cottages |
|---|---|
Lowest Price | $124 |
Highest Price | $542 |
Popular accommodation | Addie's Place: A Quiet and Quirky Guesthouse, 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, 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, Terrific 3-bedroom cottage with AC in charming Cavendish, Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit, Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!, Family-friendly Ludlow Cabin on Lake Pauline!, Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!, Picture-perfect Vermont Mtn Cabin w/ Hot Tub! |
Windsor County Cottages essential information
Accommodation | 55 Cottages |
|---|---|
Lowest Price | $124 |
Highest Price | $542 |
Popular accommodation | Addie's Place: A Quiet and Quirky Guesthouse, 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, 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, Terrific 3-bedroom cottage with AC in charming Cavendish, Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit, Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!, Family-friendly Ludlow Cabin on Lake Pauline!, Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!, Picture-perfect Vermont Mtn Cabin w/ Hot Tub! |
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