Marlboro Vacations from $1,047

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Your Marlboro Vacation

Our vacation packages to Marlboro provide endless opportunities to indulge in new sights, sounds and sensations. And with all the finer details worked out, you can breathe easy and enjoy your city escape without a care in the world. Every good trip to Marlboro should include some sightseeing. Where to go first? Southern Vermont Natural History Museum and Honora Winery are key attractions. Expedia is here to help you escape the everyday. Tailor your vacation to Marlboro to suit your style of travel, whatever that may be!

The Latest Marlboro vacation packages

Price found within the past 48 hours. Click for updated prices.
Windham Hill Inn

Windham Hill Inn

4 out of 5
Price was $1,269, price is now $1,047 per person
$1,047
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8.4/10 Very Good! (36 reviews)
The Inn is situated near the top of a mountain and surrounded by other hilltops. There are trails that help you to reconnect with nature. Our room was lovely and comfortable. There is a attention to detail in the decor of this establishment which is both delightful and humorous.

Reviewed on Jul 11, 2025

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Save 100% on your flight
Price was $2,659, price is now $2,095 per person
$2,095
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
17.2/10 Exceptional! (832 reviews)
Room was very clean and comfortable. Loved having the fireplace. Indoor parking garage was a plus with easy access to our room. We enjoyed dinner and breakfast at the restaurant. The outdoor space was fabulous with many activities.

Reviewed on Nov 14, 2025

Okemo Mountain Lodging

Okemo Mountain Lodging

3.5 out of 5
Clock Tower Base Area
Save 100% on your flight
Price was $4,739, price is now $3,928 per person
$3,928
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
7.8/10 Good! (28 reviews)
Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband spent a few hours working while I enjoyed the fitness center as well as indoor and outdoor pools. Very few people here during June.

Reviewed on Jun 26, 2025

The Weston

The Weston

5 out of 5
Save 100% on your flight
Price was $3,917, price is now $3,307 per person
$3,307
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
10/10 Exceptional! (9 reviews)
Beautiful accommodations! You can't use enough flattering adjectives for this property and it's staff!

Reviewed on Oct 10, 2025

Stay At Jimmy's

Stay At Jimmy's

3 out of 5
Price was $1,290, price is now $1,122 per person
$1,122
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
10/10 Exceptional! (44 reviews)
This property is conveniently located with on site parking. It is about 10 mins walk into downtown, there are restaurants, coffee shops and ice cream shops. Room was great, everything you needed was thought of. I would recommend it very much.

Reviewed on Oct 20, 2025

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Discover the most popular places to visit in Marlboro

The Stone Church

4.5/5(9 reviews)

After visiting The Stone Church, make a plan to see the other sights and activities in Brattleboro. While you're here, you can savor the top-notch restaurants.

The Stone Church

Vermont Marketplace

You can browse for the perfect souvenirs at Vermont Marketplace during your visit to Brattleboro. While you're here, you can savor the top-notch restaurants.

Vermont Marketplace

Hogback Mountain Conservation Area

You can take time to visit Hogback Mountain Conservation Area during your travels to Marlboro. Take in the museums while you're in the area.

Hogback Mountain Conservation Area

What to do in Marlboro

Vermont RT 100 Self Guided Driving Audio Tour

Vermont RT 100 Self Guided Driving Audio Tour

$17
per traveler
Vermont RT 100 Self Guided Driving Audio Tour
See all activities in Marlboro

Marlboro Hotel Deals

Colonel Williams Inn

Colonel Williams Inn

3 out of 5
111 Staver Road Brattleboro VT
$148 nightly
The price is $163 total per night from Nov 27 to Nov 28
$163 total
Nov 27 - Nov 28
Total with taxes and fees
9.6/10 Exceptional! (338 reviews)
Very charming place. Breakfast was really good, made fresh, very accommodating with food intolerances. Very much enjoyed my stay.

Reviewed on Oct 24, 2025

Colonel Williams Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St, North Adams, MA
Fully refundable
$123 nightly
The price is $137 total per night from Dec 15 to Dec 16
$137 total
Dec 15 - Dec 16
Total with taxes and fees
8.6/10 Excellent! (999 reviews)
Very clean and inviting Hotel located in downtown area. Very walkable area. Parking was free. Front desk very friendly and helpful. Would stay again.

Reviewed on Nov 3, 2025

Hotel Downstreet, an Ascend Collection Hotel
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
89 Grand Summit Way, West Dover, VT
$161 nightly
The price is $177 total per night from Nov 17 to Nov 18
$177 total
Nov 17 - Nov 18
Total with taxes and fees
8.6/10 Excellent! (242 reviews)
Amazing 2 big hot tubes and warm swim pool on the open air !!! A lot of restaurants around and Beautiful nature! But chairlifts was closed- so check availability

Reviewed on Oct 18, 2025

Mount Snow Grand Summit Resort
See all 1,573 properties in Marlboro
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 the Best Marlboro Vacation Packages

Marlboro Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Brattleboro Museum & Art Center, Brattleboro Bowl and Fort Dummer State Park

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Frequently asked questions

How much does a Marlboro vacation package cost?
You can grab a vacation package to this destination from $1,047 on Expedia. But how much your vacation to Marlboro costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Marlboro?
If you'd like to book a cheap Marlboro vacation package, consider planning a trip in March, April and October. You'll usually find lower prices on accommodations and flights during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Marlboro?
The ideal length of your Marlboro vacation depends on what you'd like to see. Generally, a handful of days to a week will give you time to check out all the main attractions and explore some hidden spots along the way.
How to find the best Marlboro package deals?
Bagging a cheap Marlboro package deal is a breeze with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add a few filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to view the most wallet-friendly Marlboro package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Marlboro vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll typically land a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalized Marlboro vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Marlboro?
Land incredible bargains by booking your flights early with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Marlboro adventure.
Does Expedia offer Book Now, Pay Later Marlboro vacation packages?
Jet off on your dream getaway to Marlboro with help from Expedia's Book Now, Pay Later vacations. No need to save up or wait for the next payday — we've joined forces with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stay on budget and snap up travel deals before they sell out.

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