Book Holiday Homes in Greenwood

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Featured Holiday Homes in Greenwood

The Mansion- Exclusive Private Estate on 5 Pristine Acres

The Mansion- Exclusive Private Estate on 5 Pristine Acres

Newry
With a stay at this vacation home in Newry, you'll be on the waterfront, within a 10-minute drive of Sunday River and Sunday River.
The Mansion- Exclusive Private Estate on 5 Pristine Acres
Dog-friendly Woodland home near ski resort with firepit

Dog-friendly Woodland home near ski resort with firepit

Greenwood
Located in Greenwood, this vacation home is in the mountains, a 5-minute walk from Mt. Abram and within a 5-minute drive of Tucker's Tumble Glades.
Dog-friendly Woodland home near ski resort with firepit
The Artist's Cabin at Powder Ridge Overlooking Sunday River
SKI PARKING PASS

The Artist's Cabin at Powder Ridge Overlooking Sunday River SKI PARKING PASS

Newry
With a stay at this vacation home in Newry, you'll be within a 10-minute drive of Sunday River and Sunday River.
The Artist's Cabin at Powder Ridge Overlooking Sunday River SKI PARKING PASS
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Sunday River Retreat | 3 Bed, 3 Bath

Sunday River Retreat | 3 Bed, 3 Bath

Newry
With a stay at this vacation home in Newry, you'll be within a 10-minute drive of Sunday River and Sunday River.
Sunday River Retreat | 3 Bed, 3 Bath
Fully renovated home with lake view, dock & mooring access, kayaks, & deck

Fully renovated home with lake view, dock & mooring access, kayaks, & deck

Harrison
With a stay at this vacation home in Harrison, you'll be on a lake, just steps from Long Lake and a 3-minute drive from Deertrees Theatre and Cultural ...
Fully renovated home with lake view, dock & mooring access, kayaks, & deck
An Authentic Clean & Cozy Maine Homestay

An Authentic Clean & Cozy Maine Homestay

Buckfield
The price is AU$330 per night from 26 Dec to 27 Dec
AU$330
includes taxes & fees
26 Dec - 27 Dec
With a stay at this vacation home in Buckfield, you'll be 27.1 mi (43.6 km) from White Mountain National Forest and 10.6 mi (17 km) from McLaughlin Gardens.
An Authentic Clean & Cozy Maine Homestay
JORDAN RUN -Minutes To Mountain. Hot Tub, Fireplace, Fire Pit,  Pet Friendly.

JORDAN RUN -Minutes To Mountain. Hot Tub, Fireplace, Fire Pit, Pet Friendly.

Newry
The price is AU$1,129 per night from 8 Jan to 9 Jan
AU$1,129
includes taxes & fees
8 Jan - 9 Jan 2025
When you stay at this vacation home in Newry, you'll be on a river, within a 15-minute drive of Sunday River and White Mountain National Forest.
JORDAN RUN -Minutes To Mountain. Hot Tub, Fireplace, Fire Pit, Pet Friendly.
Dog-Friendly Slopeside Condo - Walk to Slopes - Fireplace, Firepit & WiFi

Dog-Friendly Slopeside Condo - Walk to Slopes - Fireplace, Firepit & WiFi

Newry
When you stay at this vacation home in Newry, you'll be in the mountains, just steps from Sunday River and 5 minutes by foot from White Heat Ski Lift.
Dog-Friendly Slopeside Condo - Walk to Slopes - Fireplace, Firepit & WiFi
Getaway Lakefront Home for Skiing or Summer Enjoyment

Getaway Lakefront Home for Skiing or Summer Enjoyment

Bryant Pond
Located in Bryant Pond, this vacation home is on the waterfront, within a 15-minute drive of Mineral Collector and Mt. Abram.
Getaway Lakefront Home for Skiing or Summer Enjoyment
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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.

Greenwood Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Greenwood vacation homes are the perfect way for you to wing it.

Holiday houses in Greenwood let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Greenwood in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Greenwood adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Greenwood with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Greenwood vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Greenwood Holiday Homes essential information

Accommodation
410 Holiday Homes
Lowest Price
AU$185
Highest Price
AU$1,129
Popular accommodation
The Mansion- Exclusive Private Estate on 5 Pristine Acres, Dog-friendly Woodland home near ski resort with firepit, The Artist's Cabin at Powder Ridge Overlooking Sunday River SKI PARKING PASS, Sunday River Retreat | 3 Bed, 3 Bath, Fully renovated home with lake view, dock & mooring access, kayaks, & deck, An Authentic Clean & Cozy Maine Homestay, JORDAN RUN -Minutes To Mountain. Hot Tub, Fireplace, Fire Pit, Pet Friendly., Dog-Friendly Slopeside Condo - Walk to Slopes - Fireplace, Firepit & WiFi, Getaway Lakefront Home for Skiing or Summer Enjoyment

Top trending hotels in Greenwood

Jordan Hotel

Jordan Hotel

3 out of 5
27 Grand Circle, Newry, ME
The price is AU$396 per night from 5 Jan to 6 Jan
AU$396
includes taxes & fees
5 Jan - 6 Jan 2025
Located in Newry, Jordan Hotel is in the mountains, a 1-minute drive from Sunday River and 6 minutes from Sunday River Golf Club.
Jordan Hotel
Oxford Casino Hotel

Oxford Casino Hotel

3 out of 5
777 Casino Way, Oxford, ME
Fully refundableReserve now, pay when you stay
The price is AU$185 per night from 1 Jan to 2 Jan
AU$185
includes taxes & fees
1 Jan - 2 Jan 2025
Located in Oxford, Oxford Casino Hotel is a 1-minute drive from Oxford Casino and 6 minutes from Oxford Plains Speedway.
Oxford Casino Hotel
Hampton Inn Oxford

Hampton Inn Oxford

2.5 out of 5
151 Main St, Oxford, ME
Fully refundableReserve now, pay when you stay
The price is AU$191 per night from 29 Dec to 30 Dec
AU$191
includes taxes & fees
29 Dec - 30 Dec
Located in Oxford, Hampton Inn Oxford is in a rural location, a 1-minute drive from Oxford Casino and 6 minutes from Oxford Plains Speedway.
Hampton Inn Oxford
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Snow Cap Inn

Snow Cap Inn

2.5 out of 5
9 Snow Cap Rd, Sunday River Ski Resort, Newry, ME
The price is AU$230 per night from 5 Jan to 6 Jan
AU$230
includes taxes & fees
5 Jan - 6 Jan 2025
Located in Newry, Snow Cap Inn is in the mountains, a 1-minute drive from Sunday River and 9 minutes from Bethel Chamber of Commerce.
Snow Cap Inn
Don't see what you're looking for?
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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.

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^Subject to availability and chosen travel dates.