Woodford Vacations from $288

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Your Woodford Vacation

Our Woodford vacation packages give you endless opportunities to enjoy new sights, sounds and smells. And with all the travel planning taken care of, you can kick back and enjoy your city getaway in the way that you deserve. Make your trip to Woodford even more fun and exciting by including some sightseeing. Prospect Mountain Cross-Country Ski Center, Bennington Potters Yard and Prospect Mountain Nordic Ski Center are some of the most popular attractions you'll want to explore. Your ideal Woodford vacation is only clicks away. Explore flights, accommodations and more on Expedia for an adventure that's tailored just for you.

The Latest Woodford vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Save 100% on your flight
Price was $430, price is now $288 per person
$288
per person
Feb 28 - Mar 3
found 3 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
9.2/10 Wonderful! (218 reviews)
The place was fantastic in every way, clean, great service, beautiful location and close to everything you want to do in and around Saratoga Springs. I will book this beautiful spot again!

Reviewed on Dec 1, 2025

Saratoga Lakeside Retreat

Saratoga Lakeside Retreat

2 out of 5
Price was $2,470, price is now $1,885 per person
$1,885
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
10/10 Exceptional! (2 reviews)
The Adelphi Hotel

The Adelphi Hotel

4 out of 5
Downtown Saratoga Springs
Price was $624, price is now $505 per person
$505
per person
Feb 28 - Mar 3
found 3 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
9.8/10 Exceptional! (906 reviews)
beautiful rooms, great location, helpful staff

Reviewed on Dec 1, 2025

Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was $475, price is now $393 per person
$393
per person
Feb 28 - Mar 3
found 3 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
9.2/10 Wonderful! (1,001 reviews)
We loved our room overlooking the racetrack. The trotters were warming up on the track which was fun to watch

Reviewed on Dec 2, 2025

The Springwater B&B

The Springwater B&B

4 out of 5
Price was $435, price is now $362 per person
$362
per person
Feb 28 - Mar 3
found 3 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
10/10 Exceptional! (556 reviews)
All the staff are friendly and awesome, you feel at home. I will be back tomorrow at this wonderful place.

Reviewed on Nov 10, 2025

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Discover the most popular places to visit in Woodford

Bennington Battle Monument showing landscape views

Bennington Battle Monument

4.5/5(71 reviews)

Learn about the local history of Old Bennington when you spend time at Bennington Battle Monument. In the area, take in the art scene and mountain views.

Bennington Battle Monument
2017

Old First Congregational Church

5/5(4 reviews)

Find out about the history of Old Bennington with a stop at Old First Congregational Church. In the area, take in the art scene and mountain views.

Old First Congregational Church

Prospect Mountain Cross-Country Ski Center

4.5/5(11 reviews)

Hit the slopes in Woodford with a visit to Prospect Mountain Cross-Country Ski Center. In the area, take in the festivals and mountain views.

Prospect Mountain Cross-Country Ski Center

What to do in Woodford

Vermont RT 100 Self Guided Driving Audio Tour

Vermont RT 100 Self Guided Driving Audio Tour

$17
per traveler
Vermont RT 100 Self Guided Driving Audio Tour
See all activities in Woodford

Woodford Hotel Deals

Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

Woodford VT
8.6/10 Excellent! (3 reviews)
Perfect cottage on the water!! Enjoyed kayaking and pedal boat with family. Beautiful greenery! Very quick respond.

Reviewed on Aug 6, 2025

Get rates
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access
Cozy, welcoming, 3-bedroom cabin abutting the Green Mountain National Forest!

Cozy, welcoming, 3-bedroom cabin abutting the Green Mountain National Forest!

Woodford VT
$404 nightly
The price is $453 total per night from Dec 5 to Dec 6
$453 total
Dec 5 - Dec 6
Total with taxes and fees
This Cozy Cabin was amazing. Chris and Nicole were great hosts who were very responsive and courteous to make our trip as relaxing as we needed. They left detailed instructions on how the place operated and made sure the place was ready to go for when we arrived. If you want to get away for some ...

Reviewed on Nov 17, 2025

Cozy, welcoming, 3-bedroom cabin abutting the Green Mountain National Forest!
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $208 total per night from Dec 9 to Dec 10
$208 total
Dec 9 - Dec 10
Total with taxes and fees
9.6/10 Exceptional! (546 reviews)
Good room size, staff was wonderful. Location is prime.

Reviewed on Nov 29, 2025

The Williams Inn
See all 1,851 properties in Woodford
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 Woodford Vacation Packages

Woodford Essential Information

Language
English
Currency
U.S dollars
Top Sights
Prospect Mountain Cross-Country Ski Center, Woodford State Park and Prospect Mountain Nordic Ski Center

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Frequently asked questions

How much does a Woodford vacation package cost?
Offering great value package deals from $288 on Expedia, you'll be thrilled with how little a vacation to Woodford costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Woodford?
If you're looking to score a cheap Woodford vacation package, consider traveling in September, October and November. You'll usually find lower rates on flights and accommodations during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Woodford?
Typically, a handful of days is enough to see the top attractions during your Woodford vacation. However, if you prefer to have some time to relax or take day trips, consider extending your trip.
How to find the best Woodford package deals?
Landing a cheap Woodford package deal is a cinch with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Woodford package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Woodford vacation as a package?
You can enjoy significant savings on your next Woodford break by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to view some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Woodford?
If you're considering a spur-of-the-moment Woodford trip, 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 terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Woodford?

  1. Choose when to travel: Check your diary and get packing. Your preferred time of year and the type of activities available will also help you decide when to escape to Woodford.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and meals to flights and experiences. Your accommodations will probably be the biggest expense during your trip to Woodford.
  3. Use our trip planning tool to discover Woodford: Research every aspect of your trip to Woodford with this comprehensive planner. Invite friends or family to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Decide your trip length: Think about how long you'd like to spend exploring Woodford. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  5. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Woodford vacation package that brings all your bookings together.
  6. Book any activities or day trips: Now to the fun part — locking in everything you want to see and do. Explore some of the top things to do in Woodford and reserve your tickets early to save time (and maybe some cash too!).

Does Expedia offer Book Now, Pay Later Woodford vacation packages?
Your Woodford getaway should be a relaxing escape from your busy life, not a reason for money-related stress. So to give you that extra flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden 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.