Vacation Rentals in Greenwood, ME: Compare 10+ Sites & Save

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99 Best Vacation Rentals in Greenwood (Starting from $185)

Toms Cabin On Lake Christopher
Toms Cabin On Lake Christopher
House
Bryant Pond, ME, USA
4.2k from Greenwood center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Self-catering

1 Bedroom4 Guests
7.7

Good

6 reviews

$333
Average price / night
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Pondside Getaway - Fishing, Canoeing, & Skiing
Pondside Getaway - Fishing, Canoeing, & Skiing
Ski Chalet
Greenwood, ME, 04255, United States
2.7k from Greenwood center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

4 Bedrooms8 Guests
9.4

Superb

3 reviews

$360
Average price / night
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Private Hot Tub and Sauna Bryant Pond Retreat!
Private Hot Tub and Sauna Bryant Pond Retreat!
House
Bryant Pond, ME, USA
5.6k from Greenwood center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Hot tubs, Places to stay

4 Bedrooms10 Guests
New to Booking
$733
Average price / night
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4 season lakefront house on Twitchell Pond, private dock- near skiing
4 season lakefront house on Twitchell Pond, private dock- near skiing
House
Greenwood, ME, 04255, United States
3.0k from Greenwood center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms8 Guests
10.0

Exceptional

35 reviews

$268
Average price / night
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Greenwood Condo Less Than Half-Mi From Mt Abram Bike Park
Greenwood Condo Less Than Half-Mi From Mt Abram Bike Park
Apartment
Greenwood, ME, USA
6.1k from Greenwood center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family, Condos

1 Bedroom5 Guests
9.0

Fabulous

1 reviews

$185
Average price / night
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Private Lakefront & Boat Launch! Maine Family Home
Private Lakefront & Boat Launch! Maine Family Home
Cabin
Greenwood, ME, 04255, United States
3.1k from Greenwood center

AC, Barbecue, Dryer, Free Parking, Heater, Kitchen, Microwave, No Smoking, Patio

3 Bedrooms7 Guests
New to Booking
$230
Average price / night
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Mullen Chalet
Mullen Chalet
House
Greenwood, ME, USA
6.2k from Greenwood center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Family

3 Bedrooms6 Guests
9.7

Exceptional

4 reviews

$198
Average price / night
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Ski two Mountains! February vacation weeks just became available
Ski two Mountains! February vacation weeks just became available
House
Greenwood, ME, 04255, United States
3.4k from Greenwood center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater

3 Bedrooms10 Guests
10.0

Exceptional

56 reviews

$377
Average price / night
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Lakefront Family Retreat Skiing and Mountain Biking
Lakefront Family Retreat Skiing and Mountain Biking
House
Greenwood, ME, USA
6.2k from Greenwood center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

5 Bedrooms12 Guests
New to Booking
$442
Average price / night
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Toddy's camp on the pond
Toddy's camp on the pond
Cabin
Greenwood, ME, 04255, United States
3.4k from Greenwood center

Barbecue, Free Parking, Heater, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space, Patio

2 Bedrooms4 Guests
9.6

Exceptional

10 reviews

$198
Average price / night
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Mount Abram's Chalet
Mount Abram's Chalet
Ski Chalet
Greenwood, ME, USA
6.3k from Greenwood center

Accommodations, Cabins, Cottages, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$593
Average price / night
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Mountain View Greenwood, Hot Tub, Game Room
Mountain View Greenwood, Hot Tub, Game Room
Ski Chalet
Greenwood, ME, 04255, United States
3.5k from Greenwood center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$664
Average price / night
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Bullwinkle Lodge
Bullwinkle Lodge
House
Greenwood, ME, USA
6.4k from Greenwood center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Hot tubs, Places to stay, Family

1 Bedroom8 Guests
New to Booking
$829
Average price / night
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Luxury Sunday River Chalet • Hot Tub • Sleeps 16
Luxury Sunday River Chalet • Hot Tub • Sleeps 16
House
Woodstock, ME, 04219, United States
3.8k from Greenwood center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater

4 Bedrooms16 Guests
New to Booking
$531
Average price / night
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The Bullwinkle Retreat
The Bullwinkle Retreat
House
Greenwood, ME, USA
6.4k from Greenwood center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Hot tubs, Places to stay, Family

1 Bedroom10 Guests
New to Booking
$1128
Average price / night
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Waterfront Chalet: 4BR Luxury w/ Game Room, Private Dock & Minutes to Skiing!
Waterfront Chalet: 4BR Luxury w/ Game Room, Private Dock & Minutes to Skiing!
Ski Chalet
Woodstock, ME, 04219, United States
3.9k from Greenwood center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Laundry, Microwave

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$915
Average price / night
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Bullwinkle’s Roost
Bullwinkle’s Roost
Apartment
Greenwood, ME, USA
6.4k from Greenwood center

Apartments, Accommodations, Pet-friendly, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$335
Average price / night
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Woodroad Chalet-  Ski house close to water, Hot tub, large lot
Woodroad Chalet- Ski house close to water, Hot tub, large lot
Ski Chalet
Locke Mills, ME, 04255, United States
4.0k from Greenwood center

AC, Barbecue, Dryer, Fireplace, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$592
Average price / night
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Quiet Waterfront Cabin with Dock, Game Room, Hot Tub
Quiet Waterfront Cabin with Dock, Game Room, Hot Tub
House
Greenwood, ME, USA
6.8k from Greenwood center

Spa, Hot Tub, Security/Safety, Parking, Wellness Facilities, Ocean View, Oceanfront

4 Bedrooms13 Guests
New to Booking
$589
Average price / night
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Waterfront Cabin Remastered
Waterfront Cabin Remastered
Cabin
Woodstock, ME, 04219, United States
4.2k from Greenwood center

AC, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

2 Bedrooms4 Guests
9.0

Fabulous

4 reviews

$377
Average price / night
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Birch St- Luxury on the Lake
Birch St- Luxury on the Lake
House
Woodstock, ME, 04219, United States
4.4k from Greenwood center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms10 Guests
10.0

Exceptional

22 reviews

$421
Average price / night
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Waterfront 4-bedroom home on South Pond, Greenwood
Waterfront 4-bedroom home on South Pond, Greenwood
House
Locke Mills, ME, 04255, United States
4.7k from Greenwood center

Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$672
Average price / night
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Luxury living near Sunday River
Luxury living near Sunday River
House
Greenwood, ME, 04255, United States
4.7k from Greenwood center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Laundry, Microwave

4 Bedrooms8 Guests
New to Booking
$731
Average price / night
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Getaway Lakefront Home for Skiing or Summer Enjoyment
Getaway Lakefront Home for Skiing or Summer Enjoyment
House
Bryant Pond, ME, 04219, United States
4.7k from Greenwood center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

7 Bedrooms26 Guests
10.0

Exceptional

60 reviews

$599
Average price / night
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Lakefront, Near Sunday River, Steam Rm, Firepit, HUGE Kitchen, LG Fireplace
Lakefront, Near Sunday River, Steam Rm, Firepit, HUGE Kitchen, LG Fireplace
House
Woodstock, ME, 04219, United States
4.9k from Greenwood center

Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

9 Bedrooms35 Guests
9.4

Superb

53 reviews

$1399
Average price / night
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Country House on Lake Christopher 14 Miles to Sunday River & 5 Miles to Mt Abram
Country House on Lake Christopher 14 Miles to Sunday River & 5 Miles to Mt Abram
House
Woodstock, ME, 04219, United States
5.0k from Greenwood center

Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms9 Guests
9.0

Fabulous

43 reviews

$349
Average price / night
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Apres-Ski House: 20 min to Sunday River and Steam Room
Apres-Ski House: 20 min to Sunday River and Steam Room
Cottage
Bryant Pond, ME, 04219, United States
5.0k from Greenwood center

Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$257
Average price / night
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Other accommodation types in Greenwood:

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Greenwood.

Greenwood Vacation Rentals on the Map

Frequently Asked Questions

You can explore 99 verified vacation rentals in Greenwood. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Greenwood vary depending on the season, property size, and location. Rates typically start from around $185 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Greenwood include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Greenwood welcome pets. Currently, 26 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Greenwood often include amenities such as Fireplace/Heating, Laundry, and Wellness Facilities. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.