Greenwood Vacations from $636
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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.
The Latest Greenwood vacation packages
Price found within the past 48 hours. Click for updated prices.
Pleasant Point Inn
$636
per person
Oct 3 - Oct 5
found 19 hours ago
Roundtrip flight included
New York (NYC) to Auburn (LEW)
9.6/10 Exceptional! (4 reviews)
Experienced Maine for the first time and found this lovely inn in a small community. Will definitely be planning a trip back.
Reviewed on Jul 12, 2026
Stay near popular Greenwood attractions
Mt. Abram
9.0/10 (14 reviews)
Hit the slopes in Greenwood with a visit to Mt. Abram. Stroll along this relaxing area's riverfront, or simply enjoy its bars.
Round Pond
Commune with nature and explore the great outdoors at Round Pond during your travels in Greenwood. While you're in the area, wander around the natural setting.
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.
Zephyr's Glades
You can take time to visit Zephyr's Glades during your travels to Greenwood. While you're in the area, wander around the natural setting.
Tucker's Tumble Glades
You can take time to visit Tucker's Tumble Glades during your travels to Greenwood. While you're in the area, wander around the natural setting.
Uncle Tom Mountain
Commune with nature and explore the great outdoors at Uncle Tom Mountain during your travels in Greenwood. While you're in the area, wander around the natural setting.
Greenwood Hotel Deals
Abundant Light with Hot Tub, King Bed, and Wood stove-18 Minutes to Sunday River
Greenwood ME
10/10 Exceptional! (32 reviews)
"Nice and peaceful."
Reviewed on Aug 22, 2026
Oxford Casino Hotel
777 Casino Way Oxford ME
Fully refundableReserve now, pay when you stay
$125 nightly
$136 total
Aug 31 - Sep 1
Total with taxes and fees
Grand Summit Hotel
97 Summit Road Newry ME
$134 nightly
$145 total
Sep 27 - Sep 28
Total with taxes and fees
8.4/10 Very Good! (402 reviews)
"Wonderful staff Clean room Nice pool and hot tub"
Reviewed on Aug 24, 2026
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 Greenwood Vacation Packages
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 |
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Frequently asked questions
How much does a Greenwood vacation package cost?
Offering great value package deals from $636 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
