Add Listing
    For Sale
    • For Sale
    • For Lease
    • Recently Sold
    • Property Lookup
    • Brokers
    Hospitality
    1
    • Retail
    • Office
    • Residential Income
    • Restaurants
    • Industrial
    • Mixed-Use
    • Hospitality
    • Health Care
    • Sports & Entertainment
    • Land
    • Agricultural
    • Specialty
    Price
    Price range
    $
    $
    Size
    Property size / sq.ft.
    AI Search

    Meet Realmo: The Largest Hub
    of Commercial Real     Estate in the US

    Over 1 million active listings and over 150 million property profiles

    Windsor County, VT Bed & Breakfasts for Sale

    Notify Me
    List
    Map
    Burlington, VT Bennington, VT Brattleboro, VT
    Historic Inn Near Ski Resorts
    $2,400,000

    Historic Inn Near Ski Resorts

    2 Dublin Road, Plymouth, VT 05149

    Full-service Vermont inn near Okemo and Killington ski resorts.

    • Prime location on Route 100, between Okemo Mountain Resort (±4 miles) and Killington Resort (±12 miles).
    • Historic, full‑service Vermont inn with a longstanding operating history.
    • Striking lakeside setting.
    • Benefits from year‑round tourism: skiing, lake recreation, weddings, and destination travel.
    • Scalable business model with potential for revenue growth.
    Updated: Apr 3
    View details
    Woodstock Village Inn Opportunity
    $2,599,000
    0.46 Acres

    Woodstock Village Inn Opportunity

    Wood Stock, VT 05091

    Charming 8-room Inn with owner's quarters in Woodstock, Vermont.

    • Established 8‑room Inn with a strong reputation and impressive revenue growth.
    • Includes a separate 1‑bedroom owner's quarters for convenient on‑site living.
    • Located in Woodstock, VT, recognized as one of America's most charming small towns and a popular tourist destination.
    • Features a cozy tavern and well‑regarded restaurant, enhancing guest experience and revenue potential.
    • Combines historic charm (built in 1899) with modern amenities.
    Updated: Aug 12, 2025
    View details
    Turnkey Village Inn and Restaurant
    $1,350,000
    6,069 SF

    Turnkey Village Inn and Restaurant

    Fully furnished inn and restaurant near Okemo Mountain Ski Resort.

    86 Main Street, Ludlow, VT 5149
    View details
    Barnard Inn: Event and Wedding Venue
    $2,675,000

    Barnard Inn: Event and Wedding Venue

    Charming inn and event venue near Woodstock, Vermont.

    West Woodstock, VT 05091
    View details
    Based on your search, we've compiled 8 Potential Opportunities for your consideration. Besides 4 Active listings in Windsor County, VT, we suggest exploring several alternatives: plus 4 Land Listings that present a potential for development.

    Potential Development Sites for Consideration

    Can't find the perfect fit? These Land listings present an alternative path: the potential to develop a property for your specific goals.

    Important: These AI-suggestions are a starting point, not a guarantee of permitted use. All zoning, permitting, and land use information must be independently verified by you with the appropriate local authorities before making any commitments.

    Winchester Vacant Wooded Lot
    $33,750
    5.34 Acres

    Winchester Vacant Wooded Lot

    Vacant, wooded lot with high visibility in Winchester, NH.

    0 Ashuelot Main Street, Winchester, NH 03470
    View details
    Level Lot Near Town Amenities
    $65,000
    1.90 Acres

    Level Lot Near Town Amenities

    1.9-acre lot near amenities, recreation, and ski resorts.

    TBD VT Route 15W, Johnson, VT 05656
    View details
    Commercial Land in Woodridge, NY
    $69,000
    0.46 Acres

    Commercial Land in Woodridge, NY

    Prime commercial land with utilities available in Woodridge, NY.

    *** Mountaindale Road, Fallsburg, NY 12733
    View details
    Cochecton Land on Route 17B
    $68,500
    2.00 Acres

    Cochecton Land on Route 17B

    Two acres in Hamlet District, suitable for commercial or residential.

    2.-1-32.7 State Route 17B, Cochecton, NY 12726
    View details

    Windsor County, VT Bed & Breakfasts Investment Opportunities Market Analysis

    Explore 4 bed & breakfasts for sale in Windsor County, VT, showcased through 4 active listings on our real estate platform. These investment opportunities span a total of 20,038 square feet of properties for sale, with an estimated market value of $2,599,000.

    Sale prices for inns in Windsor County, VT start at $2,599,000, averaging $2,599,000, and reaching up to $2,599,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

    List
    Map

    Bed & breakfasts by market

    Browse Bed & breakfasts for Sale Near Windsor, VT

    Popular Categories

    Select Neighborhood

    Google sign-in failed. Please try again or use another login method.
    Sign Up Successful!
    You now have access to more from Realmo!