A calm lake surrounded by autumn-colored trees and houses in the background.

Greenwood Vacations from $2,116

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The Latest Greenwood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Sep 18 - Sep 22

    Pleasant Point Inn + Flight

    Lovell
    4 nights
    2.0 star property
    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 July 12, 2026
    Roundtrip Hyannis (HYA) - Auburn (LEW)
    HYA - MHT2 stops MHT - HYA2 stops
    $2,215
    $2,116
    per traveler
    found 12 hours ago
    Pleasant Point Inn

Where to stay in Greenwood

Find the best Greenwood areas and neighborhoods for the activities you enjoy most. Learn more about Greenwood
Learn more about Greenwood

South Pond Shores

If you're looking for some top things to see and do in South Pond Shores and surrounding area, you can visit Mt. Abram and The Zone.

Discover the most popular places to visit in Greenwood

Greenwood Hotel Deals

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.

Frequently Asked Questions

How much does a Greenwood vacation package cost?

Offering great value package deals from $2,116 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.