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A small town with a church, houses, and a lake surrounded by autumn-colored trees.

Chelsea Vacations from $738

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The Latest Chelsea Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Interior
    Sep 18 - Sep 21

    The Inn at Weathersfield + Flight

    Perkinsville
    3 nights
    4.0 star property
    9.8/10 - Exceptional (80 reviews)
    Roundtrip • New York (NYC) - Lebanon (LEB)
    LGA - ALB • Nonstop ALB - LGA • Nonstop
    $805
    $738
    per traveler
    found 13 hours ago
    The Inn at Weathersfield
  • Exterior
    Aug 24 - Aug 27

    Holiday Inn Club Vacations Mount Ascutney Resort by IHG + Flight

    Brownsville
    3 nights
    3.0 star property
    9.0/10 - Wonderful (856 reviews)
    "Great"
    Reviewed June 22, 2026
    Roundtrip • Orlando (MCO) - Lebanon (LEB)
    MCO - LEB • 1 stop LEB - MCO • 2 stops
    $870
    $800
    per traveler
    found 1 day ago
    Holiday Inn Club Vacations Mount Ascutney Resort by IHG
  • 2 restaurants; breakfast and dinner served
    Aug 24 - Aug 27

    Lake Morey Resort + Flight

    Fairlee
    3 nights
    3.5 star property
    9.0/10 - Wonderful (211 reviews)
    "💕"
    Reviewed July 10, 2026
    Roundtrip • Orlando (MCO) - Lebanon (LEB)
    MCO - LEB • 1 stop LEB - MCO • 2 stops
    $1,190
    $1,102
    per traveler
    found 1 day ago
    Lake Morey Resort
  • Lobby sitting area
    Aug 24 - Aug 27

    Six South St Hotel + Flight

    Hanover
    3 nights
    2.5 star property
    9.4/10 - Exceptional (946 reviews)
    "Third year staying here. Staff is warm and friendly. They are always asking about your day, if they can help. Valet parking is easy-to-use: in,out or just need to get something out of your car. Continental breakfast is new. Everything fresh. Coffee freshly ground and hot. Rooms are clean and hotel is quiet."
    Reviewed July 13, 2026
    Roundtrip • Orlando (MCO) - Lebanon (LEB)
    MCO - LEB • 1 stop LEB - MCO • 2 stops
    $1,148
    $1,066
    per traveler
    found 1 day ago
    Six South St Hotel
  • Breakfast, lunch, dinner and brunch served
    Aug 24 - Aug 27

    Hanover Inn Dartmouth + Flight

    Hanover
    3 nights
    4.0 star property
    9.6/10 - Exceptional (961 reviews)
    "Frank at the front desk was extremely friendly and went out of his way to help. He even gave us a little tour of the place. Also Andrew was very friendly and helped us with our bags."
    Reviewed July 4, 2026
    Roundtrip • Orlando (MCO) - Lebanon (LEB)
    MCO - LEB • 1 stop LEB - MCO • 2 stops
    $1,568
    $1,471
    per traveler
    found 1 day ago
    Hanover Inn Dartmouth

Chelsea Hotel Deals

Property entrance

The Inn at Montpelier

The Inn at Montpelier
3.5 star property
19.8 mi from Chelsea
8.0 out of 10, Very Good, (387 reviews)
"Breakfast was great. And the hotel looks like it was great in its time. They appear to be painting and repairing the facility but they aren’t moving very fast. Our bed was worn out and I wouldn’t have been able to stay a fourth night. I hurt so bad after sleeping on that bed. We were there 3 nights and the four daytime days there was never any activity on the front porch as far as construction but it was blocked off for repairs. The whole town was a disappointment as far as being kept up. And...
$130 nightly
The price is $143
Jul 20 - Jul 21
Total with taxes and fees
The Inn at Montpelier
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.
See all properties in Chelsea

Frequently Asked Questions

How much does a Chelsea vacation package cost?

Offering great value package deals from $738 on Expedia, you'll be surprised at how little a vacation to Chelsea costs! Expedia's packages mean less travel planning for you and greater savings.

What are the cheapest months to go to Chelsea?

April, May and October are great times to search for cheap Chelsea vacation packages. Traveling in less busy periods means you can usually find better prices on hotels and flights.

How many days is enough for Chelsea?

The ideal duration of your Chelsea vacation depends on what you'd like to see and do. Usually, a handful of days to a week will give you enough time to check out all the top sights and explore some hidden gems along the way.

How to find the best Chelsea package deals?

Use Expedia's filter tool to find some unbeatable Chelsea package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Chelsea package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.

Is it cheaper to book a Chelsea vacation as a package?

Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally snag a better deal than booking each component separately. And you'll still have the freedom to create a personalized Chelsea vacation by choosing your preferred airline, accommodation type and car class.

When to book a vacation package to Chelsea?

If you're considering a spur-of-the-moment Chelsea getaway, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score incredible deals on your hotels and flights by booking ahead.

Does Expedia offer Book Now, Pay Later Chelsea vacation packages?

Your Chelsea getaway is meant to be an escape from your daily routine, not a reason for money-related stress. So to allow you more flexibility, we've teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.

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Things to do near Chelsea

In Chelsea, Vermont, outdoor enthusiasts will find plenty to enjoy with activities like skiing at local ski resorts and exploring scenic ski fields. For those looking for unique experiences, consider taking a bus tour to explore the area or discovering the charm of Broadway. Whether you're seeking adventure or relaxation, Chelsea offers a delightful mix of outdoor and cultural activities for a memorable vacation.

Shopping

In Chelsea, you can shop at The Country Bookshop for unique gifts, located 20 miles away. If you're up for a drive, check out the Northfield Shopping Mall and Berlin Mall, both about 15-17 miles away, offering a mix of stores in a family-friendly atmosphere.

Recreation

Catch a film at Playhouse Movie Theatre, where you can enjoy a cozy atmosphere filled with culture and family-friendly entertainment. For a day outdoors, head to Montague Golf Club for a round of golf amidst beautiful landscapes, perfect for sports enthusiasts and nature lovers alike.

Experience live performances at Chandler Music Hall, a charming venue that offers a rich cultural experience and family-friendly shows. It's a great way to soak in the local arts while enjoying a romantic night out or a fun evening with loved ones.

Adventure

Experience the thrill of racing at Thunder Road International Speedbowl, located 13 miles from Chelsea, where the excitement of motorsports comes alive. For a scenic hike, explore the Connecticut River Birding Trail, 17 miles away, offering breathtaking outdoor views. In winter, enjoy skiing at Ole's Cross Country Center, 21 miles from Chelsea.

Nightlife

In Chelsea, Vermont, enjoy a cozy nightlife with local pubs and bars offering craft beer and live music. Visit the Chelsea Green for occasional events, or unwind at the local diner where you can mingle with friendly locals and savor delicious late-night snacks.

Find the best attractions near Chelsea

Chelsea, Vermont, is perfect for outdoor and adventure enthusiasts, offering a range of activities from skiing to exploring local attractions like the library, scenic lakes, and historic college campuses. Visitors can immerse themselves in culture and family-friendly experiences while enjoying the charming landscape. For those interested in sports, consider a trip to the Chelsea Football Club, enhancing your visit with a taste of local passion.

  • Norwich University: Located 15 miles from Chelsea, Norwich University is a historic institution that radiates a rich cultural vibe. As one of the oldest private military colleges in the U.S., it offers a unique blend of tradition and modern education, showcasing stunning architecture and a vibrant campus life.
  • Knight's Spider Web Farm: Just 10 miles away, Knight's Spider Web Farm is a charming farm known for its friendly atmosphere and budget-friendly excursions. Visitors can explore the fascinating world of spiders, learn about their habitats, and even participate in hands-on activities that highlight the beauty of these often-misunderstood creatures.
  • Morrill Homestead: Only 9 miles from Chelsea, the Morrill Homestead is a historic house that offers a glimpse into Vermont's past. With its cultural ambiance, the homestead features exhibits and guided tours that delve into the life and legacy of the Morrill family, showcasing the essence of rural New England heritage.

Best time to go to Chelsea

The best time to visit Chelsea can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chelsea falls in July, when visitor numbers are high and weather is mostly sunny with light rain. The coolest average temperature in Chelsea falls in January, visitor numbers are average and weather is mostly cloudy with light rain.

Tips to save on your trip to Chelsea

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically April to May and November) for more affordable package holidays to Chelsea.
  • 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.

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