Proctorsville Vacations from $864

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The Latest Proctorsville vacation packages

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 $967, price is now $864 per person
$864
per person
May 9 - May 12
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
8.6/10 Excellent! (847 reviews)
No inflatable mattress offered anymore.

Reviewed on Mar 18, 2026

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,318, price is now $1,142 per person
$1,142
per person
May 9 - May 12
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
9.2/10 Wonderful! (567 reviews)
Always an Amazing time when we stay here. Property well maintained, staff is super friendly and the food here is above and beyond. Did I mention I got married here 👍👍

Reviewed on Apr 5, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,013, price is now $879 per person
$879
per person
May 9 - May 12
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
8.8/10 Excellent! (914 reviews)
Woodstock is a magical place! We love staying at the Shire! They really make it feel like home! So cozy! The staff is very friendly and accommodating! We will always stay at the Shire!

Reviewed on Jan 30, 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 $1,025, price is now $918 per person
$918
per person
May 9 - May 12
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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

Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 out of 5
Price was $1,031, price is now $925 per person
$925
per person
May 9 - May 12
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
9/10 Wonderful! (109 reviews)
We used to spend a good deal of time in ludlow . Recently my wife and I have been visiting about once per year. Back in the day we very much enjoyed the castle inn for its great food. We thoghtvwe would stay for a couple of nights. We hoped to ski one day. We went into the inn with a big ski bag and they wanted us to climb 3 levels with it. Luckily there was a person who became available to help. The room was a large king. The furnishings were represetative of a classic inn. Very old but not broken or too worn. However the heat was set so high it was unconfortable with no mechanism to lower it. .it was very difficult to sleep . We also learned that they dont do dinners on sundays. So we changed some long standing plans. Upon asking if they had a shuttle to ski area we were told we needed to walk to the. hotel next door. Something untenable in ski boots. When we got back went to their gym. It was nice. But locker rooms were somewhat unkept and aged out Most disappointing was after our return to the room on day two the room was not cleaned. Upon reaching out they said there was no cleaning services for overnight guests. But if we needed towels they would bring it up. Given there was no dinner we found a place closer to the highway and decided to just headed home. We wanted to love the inn. But from our viewpoint if they want to remain the wonderful experience we expected they need to reconsider there amenities for folks looking for a memorable few days

Reviewed on Mar 10, 2026

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Proctorsville Hotel Deals

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$137 nightly
The price is $148 total per night from Apr 12 to Apr 13
$148 total
Apr 12 - Apr 13
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
Have stayed here many times. Close to town and Okemo. Very convenient.

Reviewed on Mar 30, 2026

Pointe at Castle Hill Resort
Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 out of 5
2940 Route 103 Cavendish VT
$219 nightly
The price is $239 total per night from Apr 6 to Apr 7
$239 total
Apr 6 - Apr 7
Total with taxes and fees
9/10 Wonderful! (113 reviews)
Gorgeous multi bedroom suite that was perfect and spacious for our little family getaway. Loved the fireplace and we were conveniently located right near the outdoor pool.

Reviewed on Mar 16, 2026

Castle Hill Resort And Spa
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $143 total per night from Apr 22 to Apr 23
$143 total
Apr 22 - Apr 23
Total with taxes and fees
7.4/10 Good! (1,002 reviews)
was put in a room next to elevator, elevator was rubbing squeeling reported to front desk, they refused to move us, noise kept us up all night long. terrible experience. she said they didn't have any other rooms and refused to move us the hotel was clearly NOT full capacity. Elevator certificate ...

Reviewed on Mar 31, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton
See all 2,078 properties in Proctorsville
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 Proctorsville Vacation Packages

Proctorsville Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lebanon Municipal Airport (LEB)
Population
450
Max Temp Winter
30ºF
Max Temp Summer
75ºF

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Frequently asked questions

How much does a Proctorsville vacation package cost?
Offering excellent value package deals from $864 on Expedia, you'll be pleasantly surprised at how much a vacation to Proctorsville costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Proctorsville?
If you're hoping to snag a cheap Proctorsville vacation package, consider traveling in May, June and July. You'll generally find better prices on airfares and hotels during these months — perfect for a budget-friendly break.
How many days is enough for Proctorsville?
The ideal duration of your Proctorsville vacation depends on what you'd like to see and do. Usually, a few days to a week will give you enough time to check out all the major attractions and discover some hidden spots along the way.
How to find the best Proctorsville package deals?
Start your search for a Proctorsville package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Proctorsville package deal right away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Proctorsville getaway off to a flying start.
Is it cheaper to book a Proctorsville vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component individually. And you'll still have the flexibility to create a tailored Proctorsville vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Proctorsville?
Land amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Proctorsville break.
Does Expedia offer Book Now, Pay Later Proctorsville vacation packages?
Set off on your dream trip to Proctorsville with help from our Book Now, Pay Later vacations. There's no need to scrimp and save or wait for payday — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stick to your budget and snap up cheap deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.