Greenwood Vacations from $967

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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

Pleasant Point Inn

2 out of 5
Price was $1,006, price is now $967 per person
$967
per person
Aug 14 - Aug 16
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Auburn (LEW)
9.4/10 Exceptional! (3 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

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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.
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Greenwood Hotel Deals

Toddy's camp on the pond

Toddy's camp on the pond

Greenwood ME
9.8/10 Exceptional! (12 reviews)
"This was the perfect little cabin for our two night stay for a cousin's wedding. It was close enough to the amenities of Oxford, yet far enough away to enjoy the quiet. Hearing the loons is such a nice way to wake up and drink your coffee. Everything was clean, organized and informative. We took ..."

Reviewed on Jun 29, 2026

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Toddy's camp on the pond
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 Jul 19 to Jul 20
$136 total
Jul 19 - Jul 20
Total with taxes and fees
8.6/10 Excellent! (1,010 reviews)
"n"

Reviewed on Jul 11, 2026

Oxford Casino Hotel
Hampton Inn Oxford

Hampton Inn Oxford

2.5 out of 5
151 Main St Oxford ME
$114 nightly
The price is $124 total per night from Jul 20 to Jul 21
$124 total
Jul 20 - Jul 21
Total with taxes and fees
9/10 Wonderful! (1,010 reviews)
"Good breakfast, nice rooms. Site was a bit noisy, even near McCarran airport. We arrived"

Reviewed on Jul 12, 2026

Hampton Inn Oxford
See all 1,330 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.

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 $967 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.