Marlboro Vacation Packages

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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!

Top Marlboro Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was CA $1,502, price is now CA $1,264 per person
CA $1,264
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
8.6/10 Excellent! (858 reviews)
Property beautiful. Rooms very large. Staff very friendly. The only thing that was odd to me was none of our closets had rods to hang clothes on. We were going to a formal wedding, my husband had a suit and I had a long dress to hang up, but the closets had no rods, and we had 3 closets in our room. Had to hang the suit from a door handle and the long dress from the shower rod!

Reviewed on Jun 28, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was CA $2,698, price is now CA $2,097 per person
CA $2,097
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
8.8/10 Excellent! (944 reviews)
Lovely place. We stayed in room 118 with our Lab. It was ideal. Recently updated. Loved looking out over the river and ate our dinner and sipped wine on the deck. Great location for exploring Woodstock. Would return in a heart beat.

Reviewed on Jul 1, 2026

The Vesper

The Vesper

3 out of 5
Price was CA $2,023, price is now CA $1,690 per person
CA $1,690
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
9.2/10 Wonderful! (64 reviews)
Charming, clean and friendly place!

Reviewed on Jul 1, 2026

Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Clock Tower Base Area
Price was CA $1,902, price is now CA $1,591 per person
CA $1,591
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
8.8/10 Excellent! (26 reviews)
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty

Reviewed on Dec 1, 2025

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was CA $3,643, price is now CA $3,348 per person
CA $3,348
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Springfield (VSF)
9.4/10 Exceptional! (586 reviews)
Had a short stay with my family to the Woodstock Inn and would love to return some day. Hospitality at its best in a beautiful town. The grounds and amenities were immaculate and authentic to the area. A memorable stay.

Reviewed on Jun 25, 2026

Ready to book your vacation to Marlboro?

 

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Marlboro Hotel Deals

Colonel Williams Inn

Colonel Williams Inn

3 out of 5
111 Staver Road Brattleboro VT
The price is CA $206 per night from Jul 9 to Jul 10
CA $206
CA $227 total
Jul 9 - Jul 10
includes taxes & fees
9.8/10 Exceptional! (354 reviews)
"Great breakfast!"

Reviewed on May 15, 2026

Colonel Williams Inn
The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!

Brattleboro VT
The price is CA $230 per night from Jul 9 to Jul 10
CA $230
CA $436 total
Jul 9 - Jul 10
includes taxes & fees
10/10 Exceptional! (2 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"

Reviewed on Jan 11, 2026

The Studio with a View. Bring your dog, too!
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
89 Grand Summit Way West Dover VT
Fully refundable
The price is CA $219 per night from Jul 6 to Jul 7
CA $219
CA $262 total
Jul 6 - Jul 7
includes taxes & fees
8.6/10 Excellent! (284 reviews)
"Lovely resort although the pool is closed until October. Beautiful, peaceful property. 300+ rooms! Music on patio with s’mores was fun. Karen was very nice and helpful. Only negative it is 15 miles from town and not a lot to do!"

Reviewed on Jun 29, 2026

Grand Summit Resort, A Vail Resorts Property
See all 1,629 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.
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Stay near popular Marlboro attractions

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.
See properties

What to do in Marlboro

Vermont RT 100 Self Guided Driving Audio Tour

Vermont RT 100 App-Guided Driving Audio Tour

CA $24
per traveller
Vermont RT 100 App-Guided Driving Audio Tour
Mindful Forest Escape: Rebalance, reflect and connect

Mindful Forest Escape: Rebalance, reflect and connect

CA $131
per adult
Mindful Forest Escape: Rebalance, reflect and connect
See all activities in Marlboro

Frequently asked questions

How much does a Marlboro vacation package cost?
Offering excellent value package deals from CA $1,264 on Expedia, you'll be surprised at how little a vacation to Marlboro costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Marlboro?
The off-season is the best time to head to Marlboro if you're trying to keep costs down. Another tip for getting cheap Marlboro vacation packages? Avoid visiting during public holidays and any major festivals or events.
How many days is enough for Marlboro?
The ideal duration of your Marlboro vacation depends on what you'd like to do. Typically, a handful of days to a week will give you enough time to hit all the top sights and explore some hidden treasures along the way.
How to find the best Marlboro package deals?
Use Expedia's handy filters to find some great Marlboro package deals. When you begin your search, simply 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 browse for Marlboro package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Marlboro vacation as a package?
You can enjoy significant savings on your Marlboro retreat by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Marlboro?
If you're considering a spontaneous Marlboro adventure, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Marlboro?

  1. Choose your dates: What you plan to do in Marlboro and your preferred season can help you decide when to go.
  2. Work out your budget: Ensure you have enough money to cover everything from food and transportation to activities and flights. Your accommodations will likely be the biggest expense during your trip to Marlboro.
  3. Set the duration of your trip: Start by listing all the attractions and activities you want to get to in Marlboro. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a personalized Marlboro vacation package.

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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.