Plainfield Vacations from $369

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Your Plainfield Vacation

The exciting city of Plainfield is calling. Immerse yourself in everything it has to offer with a Plainfield vacation package that's custom made for you. Eager to see the sights? Spend some time enjoying top attractions like Aidron Duckworth Art Museum during your trip to Plainfield. No matter your travel plans or budget, organizing your ultimate tailored Plainfield vacation is a cinch with Expedia.

The Latest Plainfield vacation packages

Price found within the past 48 hours. Click for updated prices.
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $464, price is now $369 per person
$369
per person
Apr 9 - Apr 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Springfield (VSF)
7.6/10 Good! (1,002 reviews)
Easy check in and good parking

Reviewed on Jan 9, 2026

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $1,682, price is now $1,419 per person
$1,419
per person
Mar 6 - Mar 9
found 23 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Springfield (VSF)
8.6/10 Excellent! (834 reviews)
Clean, staff was great.

Reviewed on Dec 23, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $744, price is now $632 per person
$632
per person
Mar 6 - Mar 9
found 23 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Springfield (VSF)
8.8/10 Excellent! (881 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

Hidden Kingdom in Plymouth

Hidden Kingdom in Plymouth

2 out of 5
Price was $2,480, price is now $2,130 per person
$2,130
per person
Mar 6 - Mar 9
found 23 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Rutland (RUT)
No reviews
Beechwood Home in Mendon

Beechwood Home in Mendon

2 out of 5
Save 100% on your flight
Price was $2,888, price is now $2,484 per person
$2,484
per person
Mar 6 - Mar 9
found 23 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Rutland (RUT)
No reviews
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Plainfield Hotel Deals

Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
$120 nightly
The price is $132 total per night from Feb 1 to Feb 2
$132 total
Feb 1 - Feb 2
Total with taxes and fees
9.2/10 Wonderful! (1,093 reviews)
Very polite staff and very clean rooms.

Reviewed on Jan 27, 2026

Align Inn Vermont
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$148 nightly
The price is $160 total per night from Mar 2 to Mar 3
$160 total
Mar 2 - Mar 3
Total with taxes and fees
8.8/10 Excellent! (962 reviews)
Friendly staff, clean rooms.

Reviewed on Jan 28, 2026

Pointe at Castle Hill Resort
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$349 nightly
The price is $384 total per night from Feb 22 to Feb 23
$384 total
Feb 22 - Feb 23
Total with taxes and fees
9.2/10 Wonderful! (561 reviews)
Excellent hotel, staff well trained.

Reviewed on Jan 21, 2026

Woodstock Inn & Resort
See all 1,548 properties in Plainfield
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 Plainfield Vacation Packages

Plainfield Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lebanon Municipal Airport (LEB)
Population
210
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Blow-Me-Down Bridge, Cornish-Windsor Covered Bridge and Perkins Pond

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Frequently asked questions

How much does a Plainfield vacation package cost?
You'll find cheap prices from $369 on Expedia for your Plainfield break. However, a range of factors like the season, choice of hotel and length of stay will influence how much your vacation to Plainfield costs.
What are the cheapest months to go to Plainfield?
If you're hoping to score a cheap Plainfield vacation package, consider planning a trip in February, March and November. You'll typically find better prices on accommodations and flights during these months — ideal for budget-conscious travelers.
How many days is enough for Plainfield?
With a well-organized travel plan, you can easily hit the top Plainfield attractions in a few days. But if you prefer to discover hidden spots or go on day trips, consider booking your Plainfield vacation for longer.
How to find the best Plainfield package deals?
Use Expedia's handy filters to find some terrific Plainfield package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Plainfield package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Plainfield vacation as a package?
You can enjoy significant savings on your next Plainfield retreat by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to view some great hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Plainfield?
Score amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Plainfield vacation.
Does Expedia offer Book Now, Pay Later Plainfield vacation packages?
Your Plainfield getaway is meant to be a relaxing escape from your busy life, not a reason for money worries. So to allow you more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.