Greenwood Vacation Rentals

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Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Greenwood vacation rentals

Fridge, microwave, oven, stovetop

Mountain View Greenwood, Hot Tub, Game Room

Mountain View Greenwood, Hot Tub, Game Room
Greenwood
10.0 out of 10, Exceptional, (4 reviews)
"We had overflow of family for holidays. The space worked great with 3 floors and games and hot tub added to the stay making it work for two young families! Host was great and accommodating "
United States
Cathy H.
The price is ￥53,909
￥136,761 total
includes taxes & fees
Mar 17 - Mar 18
Mountain View Greenwood, Hot Tub, Game Room
Exterior

Cozy Winter Stay • Nut House • Near Mt & Bridgton

Cozy Winter Stay • Nut House • Near Mt & Bridgton
Bridgton
10.0 out of 10, Exceptional, (2 reviews)
"What a great little house...everything was well appointed and planned. Very easy to find and communication was excellent. Inspiring layout of home---i hope to build one like it someday."
United States
Laura H.
The price is ￥23,480
￥47,138 total
includes taxes & fees
Mar 16 - Mar 17
Cozy Winter Stay • Nut House • Near Mt & Bridgton
Smart TV, fireplace, video games, foosball

Nature Retreat, Sauna, Hot Tub, Gameroom, Fire Pit

Nature Retreat, Sauna, Hot Tub, Gameroom, Fire Pit
Woodstock
The price is ￥23,017
￥98,387 total
includes taxes & fees
Mar 31 - Apr 1
Nature Retreat, Sauna, Hot Tub, Gameroom, Fire Pit
3 bedrooms, desk, iron/ironing board, free WiFi

An Authentic Clean & Cozy Maine Homestay

An Authentic Clean & Cozy Maine Homestay
Buckfield
9.8 out of 10, Exceptional, (66 reviews)
"Very nice and comfortable house, clean and quiet. The hosts were very responsive. We had a great stay."
United States
Jessica Stebbins B.
The price is ￥19,838
￥32,767 total
includes taxes & fees
Mar 23 - Mar 24
An Authentic Clean & Cozy Maine Homestay
Terrace/patio

Charming Home Near Sunday River & Other Ski Areas

Charming Home Near Sunday River & Other Ski Areas
Rumford
9.8 out of 10, Exceptional, (86 reviews)
"Great place to stay."
United States
Sara K.
The price is ￥18,545
￥36,981 total
includes taxes & fees
Mar 17 - Mar 18
Charming Home Near Sunday River & Other Ski Areas
Interior

Unique lodging in the wilderness. Off the grid location great place to disconnect and enjoy nature. Access via foot or other in wintertime.

Unique lodging in the wilderness. Off the grid location great place to disconnect and enjoy nature. Access via foot or other in wintertime.
Chatham
9.4 out of 10, Exceptional, (28 reviews)
"This is a very remote location and finding it could have been difficult, but the host gave excellent direction"
United States
Jennifer C.
The price is ￥14,376
￥21,664 total
includes taxes & fees
Mar 16 - Mar 17
Unique lodging in the wilderness. Off the grid location great place to disconnect and enjoy nature. Access via foot or other in wintertime.
House (3 Bedrooms) | Interior

Hot Tub Fire Pit Mtn Escape Near Sunday River

Hot Tub Fire Pit Mtn Escape Near Sunday River
3.0 star property
Bethel
The price is ￥21,883
￥91,474 total
includes taxes & fees
Mar 19 - Mar 20
Hot Tub Fire Pit Mtn Escape Near Sunday River
1 bedroom, iron/ironing board, WiFi, bed sheets

Adult Themed get-a-way! Centrally located to ski mountains, Oxford Casino, OPS.

Adult Themed get-a-way! Centrally located to ski mountains, Oxford Casino, OPS.
South Paris
8.6 out of 10, Excellent, (26 reviews)
"Great location for my visit "
United States
Paul B.
The price is ￥17,970
￥27,423 total
includes taxes & fees
Mar 16 - Mar 17
Adult Themed get-a-way! Centrally located to ski mountains, Oxford Casino, OPS.
Interior

The Ellis at Chandler Brook Village

The Ellis at Chandler Brook Village
Bethel
10.0 out of 10, Exceptional, (16 reviews)
"Great get away, very calm"
United States
Ismail E.
The price is ￥28,344
￥35,073 total
includes taxes & fees
Mar 17 - Mar 18
The Ellis at Chandler Brook Village
Beach nearby

Sunnyside home near Sunday River, Black Mountain, Lakes, Rivers and Hikes

Sunnyside home near Sunday River, Black Mountain, Lakes, Rivers and Hikes
Rumford
9.4 out of 10, Exceptional, (22 reviews)
"It was the perfect spot from an excellent host "
United States
Kellen M.
The price is ￥39,773
￥79,392 total
includes taxes & fees
Mar 16 - Mar 17
Sunnyside home near Sunday River, Black Mountain, Lakes, Rivers and Hikes
1 bedroom, iron/ironing board, travel crib, free WiFi

Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES

Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES
Bridgton
10.0 out of 10, Exceptional, (22 reviews)
"Stay was great, as advertised."
United States
Mary Campbell K.
The price is ￥21,803
￥27,248 total
includes taxes & fees
Mar 16 - Mar 17
Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES
Interior

The Chapman at Chandler Brook Village

The Chapman at Chandler Brook Village
Bethel
8.8 out of 10, Excellent, (3 reviews)
"There yurts are perfect for those who wish to teeter the line between outdoor camping and staying inside a house. The bathroom facilities were above par, and there were plenty of walking trails around the property. Would stay again!"
United States
Steven B.
The price is ￥28,344
￥35,422 total
includes taxes & fees
Mar 17 - Mar 18
The Chapman at Chandler Brook Village
Dining

Lake Front Cabin on Desirable Highland Lake

Lake Front Cabin on Desirable Highland Lake
Bridgton
9.8 out of 10, Exceptional, (9 reviews)
"Beautiful place to stay with all the amenities."
United States
Paul J.
The price is ￥27,346
￥62,959 total
includes taxes & fees
Mar 17 - Mar 18
Lake Front Cabin on Desirable Highland Lake
Exterior

3BR Retreat Ideal for Couples & Ski Trips

3BR Retreat Ideal for Couples & Ski Trips
Mexico
10.0 out of 10, Exceptional, (2 reviews)
"Would definitely book again for next ski season. "
United States
Wesley
The price is ￥29,071
￥36,214 total
includes taxes & fees
Mar 17 - Mar 18
3BR Retreat Ideal for Couples & Ski Trips
1 bedroom, desk, free WiFi, bed sheets

Ultra Private, Crooked Reflections, Riverside Retreat, Hot Tub, Waterfront Glass

Ultra Private, Crooked Reflections, Riverside Retreat, Hot Tub, Waterfront Glass
Norway
10.0 out of 10, Exceptional, (8 reviews)
"Such a great and cozy few days away from reality, highly recommend this warm, home away from home kind of place!"
United States
Elizabeth S.
The price is ￥55,906
￥99,415 total
includes taxes & fees
Apr 6 - Apr 7
Ultra Private, Crooked Reflections, Riverside Retreat, Hot Tub, Waterfront Glass
Living area

Historic, luxurious 2 bed 2 bath private suite in Lovell, 10 mins to Kezar Lake

Historic, luxurious 2 bed 2 bath private suite in Lovell, 10 mins to Kezar Lake
Lovell
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful scenery all around the area. House was quiet and conveniently located"
United States
Laura
The price is ￥19,168
￥38,826 total
includes taxes & fees
Apr 13 - Apr 14
Historic, luxurious 2 bed 2 bath private suite in Lovell, 10 mins to Kezar Lake
Outdoor spa tub

New, Hot-Tub, Sauna, Theater, Pets ok, Private, 14min to Sunday River

New, Hot-Tub, Sauna, Theater, Pets ok, Private, 14min to Sunday River
Bethel
10.0 out of 10, Exceptional, (4 reviews)
"Great place!!! I highly recommend it."
United States
Debora
The price is ￥44,277
￥124,869 total
includes taxes & fees
Mar 16 - Mar 17
New, Hot-Tub, Sauna, Theater, Pets ok, Private, 14min to Sunday River
Smart TV, fireplace, video games, table tennis

1 Mile to Sunday River! Hot Tub! Fire Pit! Sleeps 11!

1 Mile to Sunday River! Hot Tub! Fire Pit! Sleeps 11!
Newry
10.0 out of 10, Exceptional, (8 reviews)
"Amazing spot with lots of bed space and a hot tub :) highly recommend for a group ski trip! Nate was also super communicative and helpful!"
United States
Holly H.
The price is ￥42,696
￥102,253 total
includes taxes & fees
Mar 23 - Mar 24
1 Mile to Sunday River! Hot Tub! Fire Pit! Sleeps 11!
Exterior

Ski-in/out 2-story condo with balcony, on-site indoor pool, hot tub, sauna, W/D

Ski-in/out 2-story condo with balcony, on-site indoor pool, hot tub, sauna, W/D
Newry
8.0 out of 10, Very Good, (13 reviews)
"This place is very bad. Everything is outdated and it’s not really ski in ski out. I do not recommend. I should have listened to the other reviews."
United States
Ben M.
The price is ￥31,946
￥76,186 total
includes taxes & fees
Mar 19 - Mar 20
Ski-in/out 2-story condo with balcony, on-site indoor pool, hot tub, sauna, W/D
Interior

Ski-In/Out Condo with HotTub Sauna & Pool Sleeps 6

Ski-In/Out Condo with HotTub Sauna & Pool Sleeps 6
Newry
10.0 out of 10, Exceptional, (4 reviews)
"The condo was very neat and clean. It was exactly what we were looking for."
United States
Amy
The price is ￥19,966
￥61,232 total
includes taxes & fees
Mar 23 - Mar 24
Ski-In/Out Condo with HotTub Sauna & Pool Sleeps 6
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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Top Greenwood Hotel Reviews

Hampton Inn Oxford

Hampton Inn Oxford

10/10 Excellent
"Very clean room "
Kim 1-night trip
Posted 2 hours ago
Hampton Inn Oxford

Find out more about Greenwood

Search for holiday rentals in Greenwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Greenwood using one of the methods below:

  • View our selection of featured holiday rentals in Greenwood
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  • Enter your travel dates to view the best deals on holiday rentals in Greenwood while they last

Look no further and take a look at our great range of rental properties in Greenwood!

Frequently asked questions

Can I find a vacation rental in Greenwood?

Yes, you can find vacation rentals close to the most popular points of interest in Greenwood, or you can go with a secluded option if you want a relaxing place to stay. Greenwood is known for its ski areas.

What's the top vacation rental in Greenwood?

Luxury Lakefront Estate on 155 Acres - Pickleball, Reunions & Weddings: Visitors like this Greenwood vacation home rental. It is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 10 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a library and a hot tub.

How many vacation rentals will I find in Greenwood?

With 21 Expedia vacation rentals, you're sure to find just the right place for your Greenwood stay.

What’s there to see and do in Greenwood?

While exploring the area, visit family-friendly sights like Mineral Collector, or get outside and enjoy nature at Pennesseewassee lake. While here, Mt. Abram and The Zone are other places worth a visit.

What’s a vacation rental in Greenwood like?

Vacation rentals are private properties you can stay in for several days or longer in Greenwood. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a small group gathering.