Woodford Vacations from $531

Book a Hotel + Flight or Car together to unlock savings

Photo by Evelyn Flores

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.
DoubleTree by Hilton Schenectady Downtown

DoubleTree by Hilton Schenectady Downtown

4 out of 5
Seward Place
Save 100% on your flight
Price was $787, price is now $531 per person
$531
per person
Oct 29 - Nov 3
found 4 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
8.4/10 Very Good! (677 reviews)
Comfortable and clean.

Reviewed on Aug 6, 2025

Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $1,161, price is now $634 per person
$634
per person
Oct 10 - Oct 13
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9/10 Wonderful! (2 reviews)
Prospect was a wonderful stay with very friendly staff. The property is very well maintained. We had a great time with the all the lake activities. Would definitely recommend for a quick getaway

Reviewed on Jun 23, 2025

The Perch Hotel

The Perch Hotel

2 out of 5
Save 100% on your flight
Price was $2,296, price is now $1,400 per person
$1,400
per person
Oct 10 - Oct 13
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9/10 Wonderful! (14 reviews)
Exceptional view. The sunrise from the valley view is incredible

Reviewed on Aug 16, 2025

Hampton Inn Schenectady Downtown

Hampton Inn Schenectady Downtown

2.5 out of 5
Seward Place
Save 100% on your flight
Price was $1,083, price is now $703 per person
$703
per person
Oct 29 - Nov 3
found 4 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
9/10 Wonderful! (948 reviews)
They need to replenish the shampoo, conditioner and body lotion. The bottles were empty. The woman in the breakfast area was abusive. Trying to bump into me all the time.

Reviewed on Aug 26, 2025

Kingston Carriage House

Kingston Carriage House

4 out of 5
Roundout
Save 100% on your flight
Price was $1,322, price is now $927 per person
$927
per person
Oct 10 - Oct 13
found 22 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9.2/10 Wonderful! (21 reviews)
I liked the record player and the room was clean and comfy. Coffee and pastries were waiting by the door in the morning. Checking in, the battery was dead in the room lock. Had to wait 30 mins for service to arrive. The shower floor was dangerously slippery! An accident waiting to happen. Was unable to connect to Wi-Fi after multiple tries.

Reviewed on Aug 3, 2025

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Discover the most popular places to visit in Woodford

Bennington Battle Monument showing landscape views

Bennington Battle Monument

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

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

Hemmings Motor News Car Lover's Convenience Store & Vehicle Display

You can spend an afternoon browsing the exhibits at Hemmings Motor News Car Lover's Convenience Store & Vehicle Display in Bennington. While you're here, you can savor the charming coffeehouses.

Hemmings Motor News Car Lover's Convenience Store & Vehicle Display

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
8/10 Very Good! (2 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
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
Fully refundableReserve now, pay when you stay
$174 nightly
The price is $192 total per night from Sep 7 to Sep 8
$192 total
Sep 7 - Sep 8
Total with taxes and fees
7.2/10 Good! (516 reviews)
"When we arrived the front desk had 2 people working with numerous check ins as there was a convention checking in as well as other guests. They were understaffed in many departments. The elevator rug needed replacement as it was dirty and worn. The side entrances were full of large spider webs and ..."

Reviewed on Aug 21, 2025

The Equinox Golf Resort & Spa
Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $169 total per night from Sep 28 to Sep 29
$169 total
Sep 28 - Sep 29
Total with taxes and fees
8.6/10 Excellent! (1,007 reviews)
"Good value."

Reviewed on Aug 25, 2025

Hotel Downstreet, Ascend Hotel Collection
See all 1,775 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.

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Frequently asked questions

How much does a Woodford vacation package cost?
Offering great value package deals from $531 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.