Book Holiday Homes in Greenwood

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Featured Holiday Homes in Greenwood

Whispering Waters Farmhouse/Barn

Whispering Waters Farmhouse/Barn

Buckfield
With a stay at this vacation home in Buckfield, you'll be on a lake, and 26.6 mi (42.8 km) from White Mountain National Forest and 29.9 mi (48.2 km) from Sebago ...
Whispering Waters Farmhouse/Barn
Epic Views, GameRm+Theatre, HTub, Sauna, 9mi Sunday River

Epic Views, GameRm+Theatre, HTub, Sauna, 9mi Sunday River

Bethel
Located in Bethel, this vacation home is on a river, within a 10-minute drive of Androscoggin River and Bethel Chamber of Commerce.
Epic Views, GameRm+Theatre, HTub, Sauna, 9mi Sunday River
Our Happy Place on the Lake

Our Happy Place on the Lake

Oxford
Located in Oxford, this vacation home is within a 10-minute drive of Oxford Plains Speedway and Oxford Casino.
Our Happy Place on the Lake
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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
Bethel Village Escape with King Bed

Bethel Village Escape with King Bed

Bethel
The price is AU$337 per night from 23 Apr to 24 Apr
AU$337
includes taxes & fees
23 Apr - 24 Apr
With a stay at this vacation home, you'll be centrally located in Bethel, within a 15-minute drive of White Mountain National Forest and Sunday River.
Bethel Village Escape with King Bed
White Cap B-113 | 1 Bed, 1 Bath

White Cap B-113 | 1 Bed, 1 Bath

Newry
With a stay at this vacation home in Newry, you'll be a 1-minute walk from Sunday River and 9 minutes by foot from Barker Mountain Express Ski Lift.
White Cap B-113 | 1 Bed, 1 Bath
Sleeps 16! Arcade! Hot Tub! Fireplace! DOGS OK!

Sleeps 16! Arcade! Hot Tub! Fireplace! DOGS OK!

Bethel
The price is AU$1,383 per night from 23 Apr to 24 Apr
AU$1,383
includes taxes & fees
23 Apr - 24 Apr
Located in Bethel, this vacation home is in the mountains, within a 10-minute drive of Bethel Chamber of Commerce and Bethel Pathway.
Sleeps 16! Arcade! Hot Tub! Fireplace! DOGS OK!
Welcome to The Bear's Den! Dog friendly and 5 minutes to Pleasant Mountain!

Welcome to The Bear's Den! Dog friendly and 5 minutes to Pleasant Mountain!

Bridgton
With a stay at this vacation home in Bridgton (West Bridgton), you'll be a 4-minute walk from Moose Pond and within a 5-minute drive of Shawnee Peak.
Welcome to The Bear's Den! Dog friendly and 5 minutes to Pleasant Mountain!
Expansive Retreat - All-Season Contemporary Farmhouse  [Lakes & Mountains]

Expansive Retreat - All-Season Contemporary Farmhouse [Lakes & Mountains]

Harrison
Located in Harrison, this vacation home is in a rural location, a 4-minute drive from Long Lake and 7 minutes from Deertrees Theatre and Cultural Center.
Expansive Retreat - All-Season Contemporary Farmhouse [Lakes & Mountains]
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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
531 Holiday Homes
Lowest Price
AU$207
Highest Price
AU$1,383
Popular accommodation
Whispering Waters Farmhouse/Barn, Epic Views, GameRm+Theatre, HTub, Sauna, 9mi Sunday River, Our Happy Place on the Lake, Fully renovated home with lake view, dock & mooring access, kayaks, & deck, Bethel Village Escape with King Bed, White Cap B-113 | 1 Bed, 1 Bath, Sleeps 16! Arcade! Hot Tub! Fireplace! DOGS OK!, Welcome to The Bear's Den! Dog friendly and 5 minutes to Pleasant Mountain!, Expansive Retreat - All-Season Contemporary Farmhouse [Lakes & Mountains]

Top trending hotels in Greenwood

Jordan Hotel

Jordan Hotel

3 out of 5
27 Grand Circle, Newry, ME
The price is AU$251 per night from 1 May to 2 May
AU$251
includes taxes & fees
1 May - 2 May
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
Snow Cap Inn

Snow Cap Inn

2.5 out of 5
9 Snow Cap Rd, Sunday River Ski Resort, Newry, ME
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
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$213 per night from 28 Apr to 29 Apr
AU$213
includes taxes & fees
28 Apr - 29 Apr
Located in Oxford, Oxford Casino Hotel is a 1-minute drive from Oxford Casino and 6 minutes from Oxford Plains Speedway.
Oxford Casino Hotel
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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$207 per night from 29 Apr to 30 Apr
AU$207
includes taxes & fees
29 Apr - 30 Apr
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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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.