Owner Direct Vacation
Rentals in Greenwood
The Best Owner Direct Vacation Rentals in Greenwood. Explore thousands of vacation home rentals, large cabins, and villas near Greenwood
GUESTS
Explore the Best Greenwood Vacation Homes
Looking for the perfect place to stay in Greenwood? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Greenwood character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
- Balcony/Terrace
- Security/Safety
- Sports/Activities
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Security/Safety
- Parking
- Pet Friendly
- Security/Safety
- Parking
- TV
- Balcony/Terrace
- Balcony/Terrace
- Security/Safety
- Sports/Activities
- Parking
- Pet Friendly
- TV
- Parking
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Parking
- TV
- Balcony/Terrace
- Security/Safety
- Sports/Activities
- Parking
- Pet Friendly
- TV
- Parking
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- TV
- Balcony/Terrace
- Security/Safety
- Sports/Activities
- Parking
- TV
- Balcony/Terrace
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Parking
- Pet Friendly
- Security/Safety
- Parking
- Pet Friendly
- TV
- Parking
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Parking
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Parking
- Pet Friendly
- Security/Safety
- Parking
- Pet Friendly
- TV
- Parking
- Pet Friendly
- Security/Safety
- Parking
- Pet Friendly
- TV
- Air Conditioner
- Pet Friendly
- Designated Smoking Area
- Parking
- Security/Safety
- Fireplace/Heating
Why Travelers Love Using
Owner Direct to
Find Greenwood Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Greenwood
- Balcony/Terrace
- Security/Safety
- Sports/Activities
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Security/Safety
- Parking
- Pet Friendly
- Security/Safety
- Parking
- TV
- Balcony/Terrace
- Balcony/Terrace
- Security/Safety
- Sports/Activities
- Parking
- Pet Friendly
- TV
- Parking
- Pet Friendly
- Security/Safety
Popular Neighborhoods for Greenwood Vacation Rentals
Discover the top neighborhoods in Greenwood and choose a place that suits your stay.
Saturday May 16
Greenwood, Maine
More Vacation Rentals You May Like Near Greenwood
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
How to Reserve Your Greenwood Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Greenwood Vacation Rental FAQs
There are a lot of options in Greenwood. If you plan on staying in the Greenwood area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Greenwood:
- Ski two Mountains! February vacation weeks just became available
- 4 season lakefront house on Twitchell Pond, private dock- near skiing
- Abundant Light with Hot Tub, King Bed, and Wood stove-18 Minutes to Sunday River
- Exquisite Rustic Modern Ski Haus Right on MT Abram Bike Park
- AC for comfort this summer!
- Winter on North Pond! Ski Sunday River/Mt Abram
- 360 Degree Mountain Views- Where Sunsets Steal the Show. Dog Friendly
- Greenwood Condo < Half-Mi From Mt Abram Bike Park
- Welcoming 2-bedroom house with AC in Greenwood
- Woodroad Chalet- Ski house close to water, Hot tub, large lot
If you are looking for a family-friendly vacation home in Greenwood, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Greenwood:
Currently, the total number of properties listed in 2026 is over 77 in the Greenwood area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Greenwood.