The Bennington County Court House with a white facade, green shutters, and a gold dome.

Southern Vermont Vacations from $420

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Your Southern Vermont Vacation

Leave all the planning up to us with a Southern Vermont vacation package. With everything organized before you leave, the only thing left for you to do is sit back, relax and enjoy this destination's culture and beauty. With so much to see on a trip to Southern Vermont, it can be hard to know where to start. Kick off your journey in Brattleboro at Spofford Lake and The Stone Church — two popular attractions here. Another great city to add to your itinerary is Manchester Center. Be sure not to miss Stratton Mountain Resort and Green Mountain National Forest. Expedia has hotels, flights and all your other travel needs to help you put together your very own tailored Southern Vermont vacation today.

The Latest Southern Vermont Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 21 - Jan 24

    The Shire Woodstock + Flight

    Woodstock
    3 nights
    3.0 star property
    8.8/10 - Excellent (1,000 reviews)
    "The manager and owners do not help with any situation. My room was not clean. Pubic hairs in the shower. Hairs all over the floor, spiders, crumbs all over the valet. Baseboards were covered in filth. No one would return my calls, emails or text messages."
    Reviewed October 30, 2026
    Roundtrip • Boston (BOS) - Springfield (VSF)
    BOS - RUT • Nonstop RUT - BOS • Nonstop
    $561
    $420
    per traveler
    found 13 hours ago
    The Shire Woodstock
  • Jan 21 - Jan 25

    The Cornell Inn, Lenox & The Berkshires + Flight

    Lenox
    4 nights
    3.5 star property
    9.4/10 - Exceptional (1,001 reviews)
    Roundtrip • San Juan (SJU) - Albany (ALB)
    SJU - ALB • 1 stop ALB - SJU • 2 stops
    $815
    $535
    per traveler
    found 1 day ago
    The Cornell Inn, Lenox & The Berkshires
  • Jan 21 - Jan 24

    The Suites at Killington Center + Flight

    Killington
    3 nights
    3.5 star property
    Roundtrip • Boston (BOS) - Rutland (RUT)
    BOS - RUT • Nonstop RUT - BOS • Nonstop
    $1,598
    $1,134
    per traveler
    found 13 hours ago
    The Suites at Killington Center
  • Jan 21 - Jan 25

    The Ponds at Foxhollow + Flight

    Lenox
    4 nights
    3.0 star property
    8.4/10 - Very good (157 reviews)
    "liked it was clean . furniture is dated. Roads need repair . too many potholes"
    Reviewed November 2, 2026
    Roundtrip • San Juan (SJU) - Albany (ALB)
    SJU - ALB • 1 stop ALB - SJU • 2 stops
    $641
    $474
    per traveler
    found 1 day ago
    The Ponds at Foxhollow
  • Jan 21 - Jan 24

    Pointe at Castle Hill Resort + Flight

    Cavendish
    3 nights
    3.5 star property
    8.8/10 - Excellent (1,000 reviews)
    Roundtrip • Boston (BOS) - Rutland (RUT)
    BOS - RUT • Nonstop RUT - BOS • Nonstop
    $646
    $486
    per traveler
    found 13 hours ago
    Pointe at Castle Hill Resort

Discover the most popular places to visit in Southern Vermont

Southern Vermont Hotel Deals

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.

Find out more about Southern Vermont

Things to do near Southern Vermont

Southern Vermont is perfect for outdoor enthusiasts and adventure seekers, offering a variety of activities such as skiing at renowned ski resorts and exploring scenic ski fields. Ideal for day trips and romantic getaways, visitors can enjoy cultural excursions and cozy weekends in this picturesque region. Whether you're hitting the slopes or indulging in local charm, Southern Vermont promises a memorable vacation experience.

Shopping

For shopping in Southern Vermont, visit the Manchester Designer Outlets, 12 miles away, featuring a mix of brand-name stores. Closer options include Sugar Shack, 11 miles away, for unique gifts, and Margie's Muse Handweaving & Gallery, 7 miles away, showcasing handcrafted items.

Recreation

Experience the stunning Mount Snow Golf Course, just 7 miles away, where you can enjoy a round of golf surrounded by beautiful landscapes. For relaxation, visit Dana L. Thompson Memorial Park, 13 miles away, offering tranquil spaces for wellness activities. Finally, immerse yourself in culture at the Dorset Playhouse, located 18 miles away.

Adventure

Mount Snow, located 4 miles from Southern Vermont, offers thrilling skiing experiences amidst stunning scenery. Stratton Mountain Resort, 6 miles away, combines skiing with outdoor adventures in a vibrant atmosphere. The Grand Summit Express Ski Lift, also 4 miles from Southern Vermont, provides easy access to exhilarating slopes.

Nightlife

Southern Vermont's nightlife features cozy pubs and vibrant music scenes. Visit the Brattleboro Museum & Art Center for unique events, or enjoy local brews at the Vermont Beer Makers. For live entertainment, check out The Latchis Theatre for movies and performances that capture the local spirit.

Find the best attractions near Southern Vermont

Southern Vermont offers a perfect blend of outdoor adventures, skiing, and cultural experiences. Visitors can explore beautiful state parks, enjoy the charm of historic houses, and unwind at ski resorts. For a romantic getaway, consider the picturesque surroundings and quaint Vermont country stores that enhance the region's appeal. Whether you're seeking adventure or relaxation, Southern Vermont has something for everyone to enjoy.

  • Stratton Mountain Resort: Located 6 miles from Southern Vermont, Stratton Mountain Resort offers an exhilarating ski experience with trails for all skill levels. Beyond skiing, enjoy outdoor adventures like snowboarding and hiking, all set against breathtaking mountain vistas.
  • Green Mountain National Forest: Just 7 miles away, this stunning national park is a haven for outdoor enthusiasts. Explore lush trails, picturesque scenery, and abundant wildlife, making it a perfect spot for hiking, camping, and enjoying nature's beauty.
  • Golf Club at Equinox: Situated 12 miles from Southern Vermont, this charming golf course combines a challenging game with picturesque surroundings. Enjoy a round of golf in a serene setting, followed by premium accommodations and relaxing amenities.

Best time to go to Southern Vermont

The best time to visit Southern Vermont is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

Tips to save on your trip to Southern Vermont

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Southern Vermont.
  • Consider traveling during the off-peak season (typically April to May and November) for more affordable package holidays to Southern Vermont.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Frequently Asked Questions

What's included in a Southern Vermont vacation package?

A Southern Vermont vacation package in West Dover lets you combine flights, hotel stays, and rental cars. About half of the hotels in West Dover offer free breakfast, and nearly a third provide airport shuttle service, often connecting to Hartford, CT (BDL-Bradley Intl.).


Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

How can I save money on a Southern Vermont vacation package?

When you bundle, you can save up to 30%*. To save money on a Southern Vermont package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

Which destinations should I consider for a Southern Vermont vacation?

For a Southern Vermont vacation, consider basing your trip in one of these destinations, each offering a slightly different experience for outdoor enthusiasts:

  • West Dover: As the area with the most lodging choices, West Dover is a central base for accessing major ski resorts and a wide range of outdoor activities.
  • Wilmington: This destination offers a good selection of lodging and is well-suited for travelers looking for a slightly quieter base while still being close to skiing and adventure sports.
  • Stratton: Ideal for those prioritizing direct access to mountain activities, this area provides convenient stays for skiing and other outdoor pursuits.

Is Southern Vermont better suited for a beach vacation or a cultural trip?

Southern Vermont is primarily an outdoor and nature destination, known for its scenic views and a wide array of adventure and sports activities. Travelers can enjoy skiing at resorts like Mount Snow and Stratton Mountain Resort, or explore natural areas such as Green Mountain National Forest.


Alongside its natural attractions, Southern Vermont also offers cultural experiences, with historic sites like Hildene and artistic venues such as the Southern Vermont Arts Center. For water-based recreation, visitors can head to Harriman Reservoir or Lake Raponda.


A Southern Vermont vacation package is best suited for travelers seeking active outdoor pursuits and scenic beauty, with cultural stops available to enrich the trip.

Which airport should I use for a Southern Vermont vacation?

For a Southern Vermont vacation, travelers typically use one of several regional airports that serve the wider area. Bradley International Airport (BDL) in Hartford, Connecticut, is a common choice, offering convenient access to many parts of Southern Vermont. Boston Logan International Airport (BOS) in Boston, Massachusetts, also serves as a major gateway, particularly for destinations in eastern Southern Vermont. Both airports provide onward travel options to your chosen base.

What are the top things to do in Southern Vermont?

A Southern Vermont vacation is best explored from a base like West Dover, offering access to a range of outdoor activities and scenic spots:


Browse and book things to do in Southern Vermont on Expedia.

Can I change or cancel my Southern Vermont vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Southern Vermont vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Southern Vermont vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Southern Vermont vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Southern Vermont?

To find last-minute vacation packages to Southern Vermont, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Southern Vermont vacation packages?

Free cancellation on a Southern Vermont vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Southern Vermont vacation as a package or separately?

An Expedia vacation package could land you great savings when compared to arranging flights and hotels separately. Better still, you can tailor your Southern Vermont getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Southern Vermont vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.