Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Start by selecting your hotel
Start by selecting your hotel
Start by selecting your hotel

Save up to $603 by booking Flight + Hotel.

Search 590,000 properties and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more


Windsor Vacation Packages

Come to Windsor and see its interesting attractions.

Save Time and Money with a Windsor Package Deal

Get immediate savings with your Expedia package deal. You'll save money and time simply by combining your lodging and flight bookings with us. Spend the extra money during your tour through Windsor.

When you secure a deal, you stand to save as much as $583.

Around 400 partner airlines and 321,000 hotels worldwide are ready for you to secure via our exhaustive worldwide database.

The great package deals at Expedia make budgeting for your vacation so much fun. It's go time!

Not sure about your booking? There is no extra fee from us for changing almost any reservation.

Windsor Vacation Packages

The population of this area of Central Vermont- Killington is approximately 2,000.

Montpelier, the state capital, is roughly 55 miles to the north of Windsor, and Brownsville is 4 miles to the southwest.

When the weather is fine, head over to Mt Ascutney State Park, a beautiful green space where the locals come together to spend time outdoors.

The American Precision Museum provides an enlightening experience for inquiring minds. Meander through the halls, check out the different exhibits and be sure to ask someone about any special happenings.

One of the best historic places in Windsor is Old Constitution House. Atmospheric and insightful, it should definitely be on your itinerary.

Whether you're a spiritual person or not, you're bound to uncover something that interests you at South Congregational Church.

Accommodation in Windsor

Don't expect to find a wide range of places to stay in Windsor, so it would be wise to explore the latest listings on Expedia's hotels guide.

The Kedron Valley Inn and Holiday Inn Club Vacations Mount Ascutney Resort are among the best accommodation options in and around Windsor.

*Savings based on all vacation package bookings with Flight + Hotel on Expedia.com from January through December 2017, as compared to price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.


Top Hotel Deals

See all 543 Properties in Windsor
Snapdragon Inn $135
Snapdragon Inn

Snapdragon Inn

26 Main Street, Windsor
     
    4.6
    of 5, from 14 reviews
    3.5 out of 5.0

    Situated in Windsor, this bed & breakfast is within a 10-minute walk of Old Constitution House and South Congregational Church. American Precision Museum and Cornish-Windsor Covered Bridge are also within 1 mi (2 km).

    Windsor Mansion Inn $179
    Windsor Mansion Inn

    Windsor Mansion Inn

    153 Pembroke Road, Windsor
       
      4.7
      of 5, from 19 reviews
      3.5 out of 5.0

      Situated in Windsor, this bed & breakfast is within 2 mi (3 km) of Old Constitution House, South Congregational Church, and American Precision Museum. Cornish-Windsor Covered Bridge and Path of Life Garden are also within 3 mi (5 km).

      Idyllic: C.1842 Farmhouse on 26 Acres With Breathtaking View of the Mountains
      Idyllic: C.1842 Farmhouse on 26 Acres With Breathtaking View of the Mountains

      Idyllic: C.1842 Farmhouse on 26 Acres With Breathtaking View of the Mountains

      , West Windsor
         
        5.0
        of 5, from 3 reviews
        0.0 out of 5.0

        Situated in Windsor, this historic vacation home is 2.2 mi (3.6 km) from Mt Ascutney State Park and within 9 mi (15 km) of American Precision Museum and South Congregational Church. Cornish-Windsor Covered Bridge and Old Constitution House are also within 9 mi (15 km).

        West Windsor Retreat Vacation Home 3
        West Windsor Retreat Vacation Home 3

        West Windsor Retreat Vacation Home 3

        607 Bannister Rd, Windsor
           
          3.5 out of 5.0

          Situated in Windsor, this vacation home is 4.2 mi (6.7 km) from Mt Ascutney State Park and within 12 mi (20 km) of American Precision Museum and South Congregational Church. Cornish-Windsor Covered Bridge and Old Constitution House are also within 12 mi (20 km).

          Riverfront Retreat by Cornish-windsor Bridge
          Riverfront Retreat by Cornish-windsor Bridge

          Riverfront Retreat by Cornish-windsor Bridge

          , Cornish
             
            5.0
            of 5, from 1 reviews
            0.0 out of 5.0

            Situated in a rural location, this romantic vacation home is within a 15-minute walk of American Precision Museum, South Congregational Church, and Cornish-Windsor Covered Bridge. Old Constitution House and Saint-Gaudens National Historic Site are also within 3 mi (5 km).

            Killington Mountain Lodge, BW Signature Collection $84
            Killington Mountain Lodge, BW Signature Collection

            Killington Mountain Lodge, BW Signature Collection

            2617 Killington Rd, Killington
               
              3.7
              of 5, from 950 reviews
              3.5 out of 5.0

              Conveniently near skiing facilities, this Killington hotel is located in the mountains, within 3 mi (5 km) of Killington Golf Course and Killington Resort, and close to winter sports such as cross-country skiing and snowshoeing. Pico Mountain at Killington Ski Resort and Green Mountain National Golf Course are also within 6 mi (10 km).

              Hillside Inn at Killington $65
              Hillside Inn at Killington

              Hillside Inn at Killington

              375 Killington Rd, Killington
                 
                3.4
                of 5, from 834 reviews
                2.0 out of 5.0

                Conveniently near skiing facilities, this Killington motel is located in the mountains, within 3 mi (5 km) of Gifford Woods State Park and Pico Mountain at Killington Ski Resort, and close to winter sports such as cross-country skiing and snowshoeing. Killington Resort and Green Mountain National Golf Course are also within 6 mi (10 km).

                Fireside Inn & Suites West Lebanon $120
                Fireside Inn & Suites West Lebanon

                Fireside Inn & Suites West Lebanon

                25 Airport Road, West Lebanon
                   
                  3.9
                  of 5, from 470 reviews
                  2.5 out of 5.0

                  Situated in West Lebanon, this hotel is within 3 mi (5 km) of Main Street Museum, Briggs Opera House, and New England Transportation Institute and Museum. Tupelo Music Hall is 2.5 mi (4.1 km) away.

                  Top Deals on Flights

                  These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.