Greenwood Vacations from $884
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
The Latest Greenwood vacation packages
Price found within the past 48 hours. Click for updated prices.
Pleasant Point Inn
$884
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Cincinnati (CVG) 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.
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.
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.
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.
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.
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.
Greenwood Hotel Deals
Toddy's camp on the pond
Greenwood ME
9.4/10 Exceptional! (16 reviews)
"We loved our stay on the pond! What a sweet and cozy cottage, very well appointed for a relaxing stay, with beautiful views overlooking the pond. We enjoyed canoeing, watching the eagles soar overhead, swimming, cooking in the kitchen, and just relaxing. We would love to come back."
Reviewed on Sep 27, 2026
Quiet cabin near Mt Abram and Sunday River
Greenwood ME
10/10 Exceptional! (9 reviews)
"This cabin was great! Right next to round/south pond, and 5 minutes from Mt Abram. We would definitely stay here again. Hosts were very responsive."
Reviewed on Sep 26, 2026
Oxford Casino Hotel
777 Casino Way Oxford ME
Fully refundableReserve now, pay when you stay
$109 nightly
$119 total
Oct 19 - Oct 20
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
"My room was clean and well maintained. It was also quiet and got good sleep! Amenities were very nice, especially the bathroom shower. Casino was fairly well-maintained and clean. Love the Oxford area, lots of shops and restaurants. Will stay again next year!"
Reviewed on Oct 12, 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 |
More vacations you might like
Frequently asked questions
What are the top things to do in Greenwood?
Greenwood is an outdoor and nature destination known for skiing and other adventure activities. A Greenwood vacation offers plenty of opportunities to explore the natural landscape:Browse and book things to do in Greenwood on Expedia.
How can I save money on a Greenwood vacation package?
When you bundle, you can save up to 30%*. To save money on a Greenwood package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
Do you need to rent a car in Greenwood, or is public transport enough?
For a Greenwood vacation package, renting a car is highly recommended to fully explore the area. As an outdoor and nature destination outside a city, Greenwood's attractions are spread out. While some hotels might be near specific points of interest like Mt. Abram or Sebago Lake, having your own vehicle offers the most flexibility to reach various skiing areas, lakes, and other natural sights. The closest major airport is Portland International Jetport (PWM), and a car provides direct transportation from there to your lodging. A Greenwood vacation package with flights typically bundles your airfare and hotel, but ground transportation is usually separate.
Can I change or cancel my Greenwood vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Greenwood vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Greenwood vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Greenwood vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Greenwood?
To find last-minute vacation packages to Greenwood, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Greenwood vacation packages?
Free cancellation on a Greenwood vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Greenwood vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Greenwood getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Greenwood vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.
Explore a world of travel with Expedia
- Cabin Rentals in Locke Mills
- Rv Parks in Woodstock
- Hotels near Snow Falls
- B&B in Greenwood
- Old Orchard Beach Hotels
- Bethel Hotels
- B&B in West Paris
- Hostels in West Paris
- Resorts in West Paris
- Hotels near Oxford Casino
- Hotels near Zephyr's Glades
- Waterford Hotels
- Rv Parks in West Paris
- Woodstock Hotels
- Cabin Rentals in Bryant Pond
- Hotels near Sunday River
- B&B in Woodstock
- Motels in Greenwood
- Newry Hotels
- Motels in West Paris
- Pet-Friendly Hotels in Greenwood
- Locke Mills Hotels
- Portland Hotels
- Rv Parks in Locke Mills
- Bryant Pond Hotels
- Resorts in Bryant Pond
- Lewiston Hotels
- Greenwood Hotels
- Lodges in Bryant Pond
- Cabin Rentals in Greenwood
- 3 Star Hotels in South Oxford
- Oxford Hotels
- Hilton Hotels in Norway
- Hotels near Mt. Abram
- Cabin Rentals in Bethel
- Resorts & Hotels with Spas in Greenwood
- Norway Hotels
- B&B in Bryant Pond
- Apartments in Locke Mills
- Cabin Rentals in Woodstock
- Lodges in Woodstock
- Chalets in Greenwood
- Cabin Rentals in Waterford
- Bridgton Hotels
- Cottages in Bryant Pond
- West Paris Hotels
- Locke Mountain Ski Lift
- Visit Bethel
- Tripp Pond
- Sunday River
- Oxford Casino
- Auburn Mall
- Dr. Moses Mason House
- Visit Stoneham
- Visit Locke Mills
- Narramissic Historic Farm
- The Zone
- Steamboat Landing Mini Golf
- Rumford Falls
- Rufus Porter Museum
- Grafton Notch State Park
- Snow Falls
- Visit Bryant Pond
- Norway Vacations
- Bethel Vacations
- Mt. Abram
- Saco Valley Sports Center
- Mineral Collector
- Visit West Paris
- Ll Bean Flagship Store
- The Willows Flea Market
- White Mountain National Forest
- Shagg Pond
- Sumner Vacations
- Naples Vacations
- Rome Vacations
- Visit Greenwood
- Shawnee Peak
- Streaked Mountain
- Oxford Plains Speedway
- Kezar Lake
- Newry Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
