Woodstock Valley Vacations from $294

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Woodstock Valley Vacation

Take the stress out of organizing your next amazing adventure with a Woodstock Valley vacation package. Whether you're lured here by its art, food, architecture or other highlights, there's an inexhaustible array of experiences to be had. Up for a bit of sightseeing? A trip to Woodstock Valley wouldn't be complete without visiting Bigelow Hollow State Park, Taylor Brooke Winery and other popular attractions. A couple of quick clicks is all it takes to build a customized Woodstock Valley vacation on Expedia.

The Latest Woodstock Valley vacation packages

Price found within the past 48 hours. Click for updated prices.
Copper Lantern Motor Lodge

Copper Lantern Motor Lodge

2 out of 5
Price was $338, price is now $294 per person
$294
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Worcester (ORH)
8.4/10 Very Good! (150 reviews)
We stayed for 5 nights. On the positive side the staff was friendly and helpful, and we loved the location near the river. For negative the rooms are outdated and in need of repair and renovation, and way overpriced.

Reviewed on Aug 11, 2025

Trainmasters Inn

Trainmasters Inn

3 out of 5
Price was $326, price is now $302 per person
$302
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Worcester (ORH)
9.6/10 Exceptional! (356 reviews)
Cozy Train theme B & B. Courteous service with hometown feel.

Reviewed on Aug 27, 2025

Don't see what you're looking for?
See all available trips from Columbus to Woodstock Valley
View all trips

Woodstock Valley Hotel Deals

Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

2.5 out of 5
277 Main Street (RT 131), Sturbridge, MA
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $111 total per night from Sep 7 to Sep 8
$111 total
Sep 7 - Sep 8
Total with taxes and fees
8.8/10 Excellent! (1,484 reviews)
"Got there late in the evening and the bar downstairs was still open til midnight. Enjoyed a great cocktail after a long drive from NY. Stopped by the bakery and loved the pastries and coffee. Felt very welcoming and plan to stop by again!"

Reviewed on Aug 24, 2025

Publick House Historic Inn and Country Motor Lodge
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St, Southbridge, MA
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $141 total per night from Sep 8 to Sep 9
$141 total
Sep 8 - Sep 9
Total with taxes and fees
9/10 Wonderful! (1,279 reviews)
"The place was updated and clean. Not much else you could ask for."

Reviewed on Aug 24, 2025

Wellsworth Hotel
Inn on Storrs

Inn on Storrs

3.5 out of 5
123 Storrs Road, Willimantic, CT
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $156 total per night from Sep 15 to Sep 16
$156 total
Sep 15 - Sep 16
Total with taxes and fees
Inn on Storrs
See all 206 properties in Woodstock Valley
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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Woodstock Valley vacation package cost?
You can grab a vacation package to this top destination from $294 on Expedia. But how much your vacation to Woodstock Valley costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Woodstock Valley?
If you'd like to book a cheap Woodstock Valley vacation package, consider planning a trip in December, January and February. You'll typically find lower prices on airfares and hotels during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Woodstock Valley?
The ideal length for your Woodstock Valley vacation depends on what you'd like to see. Generally, a handful of days to a week will give you time to tick off all the main attractions and discover some hidden gems along the way.
How to find the best Woodstock Valley package deals?
Use Expedia's filters to find some of the best Woodstock Valley package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Woodstock Valley package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Woodstock Valley vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging stays and flights individually. Better still, you can customize your Woodstock Valley trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Woodstock Valley?
If you've got your Woodstock Valley travel dates confirmed, book early to grab some awesome deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for quick escapes.
Does Expedia offer Book Now, Pay Later Woodstock Valley vacation packages?
Secure your dream trip to Woodstock Valley with help from Expedia's Book Now, Pay Later vacations. No need to scrimp and save or wait for your next paycheck — we've joined forces with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans mean you can spread the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's easy to stick to your budget and snap up bargains before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.