Southern Vermont Vacation Packages

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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 Centre. 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.

Top Southern Vermont Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

CA $878
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
9/10 Wonderful! (1,161 reviews)
Very spacious and inviting..Loved the coffee maker in lobby!!!! All the girls at the front desk were extremely nice and welcoming. Very clean property and great location.. to Great Barrington, Lenox, Stockbridge, and Lee with great restaurants near by in those towns as well

Reviewed on Oct 6, 2026

The Whitlock

The Whitlock

CA $968
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
8.4/10 Very good! (388 reviews)
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

CA $922
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
9.2/10 Wonderful! (996 reviews)
Went here for our 24th Wedding Anniversary!! We picked the area so we could go to the Norman Rockwell museum. To our surprise we were upgraded to a Villa. Thank you so much Becky for the accommodations. We will be back!

Reviewed on Oct 6, 2026

The Williams Inn

The Williams Inn

CA $1,116
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
9.6/10 Exceptional! (682 reviews)
Vacation Village in the Berkshires

Vacation Village in the Berkshires

CA $948
per person
Dec 9 - Dec 12
found 10 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Albany (ALB)
8.8/10 Excellent! (2,687 reviews)
Very spacious and clean room , at an affordable price vast of amenities surrounded by nature

Reviewed on Oct 6, 2026

Where to stay in Southern Vermont

Find the best Southern Vermont areas and neighborhoods for the activities you enjoy most. Learn more about Southern Vermont
An airplane wing with a view of the landscape below, including mountains and a sunset.

Manchester Village Historic District

While there might not be top attractions in Manchester Village Historic District, you can explore the larger area and discover places like Golf Club at Equinox and Southern Vermont Arts Center.

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North Bennington Historic District

Travelers like the historic sites in North Bennington Historic District, and Park McCullough House is a top attraction you might want to visit.

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Pikes Falls

Though Pikes Falls might not have many top sights, you can venture to the surrounding area to see attractions like Sunrise Express Ski Lift and Villager Ski Lift.

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A snow-capped mountain with a forested foreground and a cloudy sky.

Bromley Mountain

1 out of top 10 points of interest in this area

While visiting Bromley Mountain, you might make a stop by sights like Bromley Mountain Ski Resort and Bromley Alpine Slide.

Find hotels in Bromley Mountain
A wooden covered bridge over a river, surrounded by lush greenery and trees.

West Dummerston

Visitors to West Dummerston like its mountain views and riverfront, and West River is a sight worth a stop.

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Ready to book your vacation to Southern Vermont?

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Southern Vermont Hotel Deals

Aspen At Manchester

Aspen At Manchester

5669 Main Street Manchester Center VT
CA $147
CA $177 total
Nov 2 - Nov 3
includes taxes & fees
8.8/10 Excellent! (699 reviews)
"Great place, but a bit over priced for what it is"

Reviewed on Oct 5, 2026

Aspen At Manchester
Colonial Motel

Colonial Motel

889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
CA $118
CA $130 total
Nov 2 - Nov 3
includes taxes & fees
Colonial Motel
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

89 Grand Summit Way West Dover VT
CA $222
CA $266 total
Nov 5 - Nov 6
includes taxes & fees
8.6/10 Excellent! (314 reviews)
"Allen in the restaurant is great."

Reviewed on Oct 6, 2026

Grand Summit Resort, A Vail Resorts Property
See all 2,088 properties in Southern Vermont
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 Southern Vermont attractions

A snow-covered forest with a clear sky.

Stratton Mountain Resort

9.2/10 (365 reviews)
Spend days outside on the mountain slopes and evenings eating in the picturesque village and relaxing in cozy mountainside lodging.
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Skiers on a snowy slope with a ski lift in the background.
Photo by Doug Blackmore/Mount Snow

Mount Snow

9.2/10 (568 reviews)
Perform wild tricks on a world-class terrain park or cruise down scenic blue-graded runs at this Green Mountain ski resort in West Dover.
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A church with a tall steeple and a stone facade.

The Stone Church

8.6/10 (39 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.
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A mountain with autumn foliage.

Mount Equinox

9.6/10 (43 reviews)
Enjoy beautiful views of rivers, lakes and valley communities as you motor along the skyline drive in the Green Mountain State.
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Bromley Mountain Ski Resort

8.8/10 (160 reviews)
Hit the slopes in Peru with a visit to Bromley Mountain Ski Resort. Discover the mountain views in this quaint area.
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Magic Mountain Ski Resort

8.6/10 (74 reviews)
Hit the slopes in Londonderry with a visit to Magic Mountain Ski Resort. Discover the mountain views in this quaint area.
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Hildene

9.4/10 (148 reviews)
You can learn about the history of Manchester Center with a trip to Hildene. Discover the mountain views in this quaint area.
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Vermont Country Store

9.2/10 (382 reviews)
Enjoy an outing to Vermont Country Store during your stay in Rockingham. You can seek out the ski slopes while in the area.
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Frequently asked questions

How much does a Southern Vermont vacation package cost?
Custom build your Southern Vermont vacation package from a low CA $878. Pick from any combination of rental cars, flights and hotels to craft the trip you've long been dreaming about. Remember to add on a few experiences or tours!
How do I get a cheap travel package to Southern Vermont?
One of the easiest ways to save cash (and time) is to bundle your bookings with Expedia. Hotels, rental cars, flights and activities — we've got them all. Pick and choose the combination that best fits you and watch your savings grow. We know a package deal is never one-size-fits-all. That's why we offer more than 550 partner airlines and 1,000,000 hotel options globally, which lets you customize your Southern Vermont adventure.
What are the top hotels in Southern Vermont?
For hotels in Wilmington with friendly service and comfy beds, you can't beat Colonial Motel And Spa and Hampton Inn Brattleboro. If you plan to visit Bondville as well, you can look forward to a good night's sleep at The Equinox Golf Resort & Spa or The Autumn Inn.
How far in advance should I book my Southern Vermont vacation?
To land discount prices, book ASAP. Air carriers generally advertise flights, along with some of the lowest fares, nearly 12 months prior to departure. Hotels, car rental and activities should also be booked well in advance so you can have the pick of the bunch. If you were hoping for a last-minute getaway to Southern Vermont, there are always lots of great bargains to be had on Expedia. Check them out now!
What does an Expedia Southern Vermont travel package include?
That depends entirely on you. You can pick from a variety of Southern Vermont packages, such as a flight, hotel and rental car. You can also book a flight and a hotel, or a rental car and a flight. Once you've made your booking, you can add the fun stuff like experiences and tours. Whatever your perfect Southern Vermont trip looks like, you'll save!
What should I know before booking a Southern Vermont travel package?
Tailor deals to suit your budget with an Expedia package. Flights, hotels, rental cars — we have everything you need to plan your escape. You'll save precious cash just by bundling your bookings. Whether you're heading away on a snow and ski adventure or venturing someplace warm, your perfect getaway is just a few clicks away.
Can I choose my airline with a Southern Vermont Expedia vacation package?
Most definitely. We have access to over 550 partner airlines around the world, so you can tailor your Southern Vermont trip according to your style and budget.
If I'm not able to travel, can I cancel my Southern Vermont vacation package?
It's difficult to predict what tomorrow might bring, so it's good to know that you can cancel or change your Southern Vermont vacation package. If you made your booking in the last 24 hours, you may be entitled to a refund. If it's an older booking, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to find out more.

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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.