Greenwood Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Robbie Martin

  • Plan, book, travel with confidence

    • Better together

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

    Find the right fit

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

    Rest easy

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

Your Greenwood Vacation

Prepare to experience Greenwood in your own style with a custom Greenwood vacation package! Uncovering the charms of this city is easy with a base in a neighborhood such as Woodstock, which is good for culture, among plenty of other things. Any trip to Greenwood needs a well-thought-out itinerary. Fill yours with famous sights like Mt. Abram, Snow Falls and North Pond. Don't put off visiting this city any longer. Your ultimate Greenwood vacation is just a few clicks away with Expedia.

Discover the most popular places to visit in Greenwood

Great family skiing at Mt Abram

Mt. Abram

4.5/5(11 reviews)

Hit the slopes in Greenwood with a visit to Mt. Abram. Stroll along this relaxing area's riverfront, or simply enjoy its bars.

Mt. Abram

The Zone

You can take time to visit The Zone during your travels to Greenwood. While you're in the area, wander around the natural setting.

The Zone

Greenwood Hotel Deals

Oxford Casino Hotel

Oxford Casino Hotel

3 out of 5
777 Casino Way, Oxford, ME
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $136 total per night from Oct 13 to Oct 14
$136 total
Oct 13 - Oct 14
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
"Enthusiastic reception staff"

Reviewed on Oct 7, 2025

Oxford Casino Hotel
Jordan Hotel

Jordan Hotel

3 out of 5
27 Grand Circle, Newry, ME
$150 nightly
The price is $163 total per night from Oct 14 to Oct 15
$163 total
Oct 14 - Oct 15
Total with taxes and fees
8.6/10 Excellent! (400 reviews)
"Property looks wonderful, however the room was a bit shabby."

Reviewed on Oct 8, 2025

Jordan Hotel
Grand Summit Hotel

Grand Summit Hotel

3 out of 5
97 Summit Road, Newry, ME
$154 nightly
The price is $168 total per night from Nov 9 to Nov 10
$168 total
Nov 9 - Nov 10
Total with taxes and fees
8.2/10 Very Good! (289 reviews)
"It was very nice. Rooms are kind of small. All the beds in the room are Murphy beds. Comfortable but interesting."

Reviewed on Oct 9, 2025

Grand Summit Hotel
See all 1,254 properties in Greenwood
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.

Greenwood Essential Information

Language
English
Currency
U.S dollars
Population
830
Max Temp Winter
25ºF
Max Temp Summer
70ºF
Top Sights
Mt. Abram, Snow Falls and Papoose Pond

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 Greenwood vacation package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Greenwood costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Greenwood?
If you're hoping to book a cheap Greenwood vacation package, consider visiting in March, April and May. You're likely to find better rates on flights and hotels during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Greenwood?
With a well-organized itinerary, you can easily tick off the top Greenwood sights in a handful of days. But if you prefer to discover lesser-known spots or go on day tours, think about booking your Greenwood vacation for longer.
How to find the best Greenwood package deals?
Use Expedia's filter tool to find some unbeatable Greenwood package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Greenwood package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Greenwood 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 typically land a better deal than booking each component separately. And you'll still get the freedom to create a personalized Greenwood vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Greenwood?
If you're considering an impromptu Greenwood adventure, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find awesome deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Greenwood vacation packages?
Set off on your dream escape to Greenwood with our Book Now, Pay Later vacations. No need to save up or hold off until the next payday — we've joined forces with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no hidden or late payment fees, you can easily stick to your budget and snap up cheap deals before they disappear.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.