Greenwood Holiday Rentals

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Greenwood holiday rentals

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 HK$972
HK$1,605 total
includes taxes & fees
30 Mar - 31 Mar
An Authentic Clean & Cozy Maine Homestay
Smart TV, fireplace, video games, table football

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

Nature Retreat, Sauna, Hot Tub, Gameroom, Fire Pit
Woodstock
The price is HK$1,093
HK$4,774 total
includes taxes & fees
31 Mar - 1 Apr
Nature Retreat, Sauna, Hot Tub, Gameroom, Fire Pit
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 HK$704
HK$1,061 total
includes taxes & fees
29 Mar - 30 Mar
Unique lodging in the wilderness. Off the grid location great place to disconnect and enjoy nature. Access via foot or other in wintertime.
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, (88 reviews)
"Great place to stay."
United States
Sara K.
The price is HK$909
HK$1,812 total
includes taxes & fees
30 Mar - 31 Mar
Charming Home Near Sunday River & Other Ski Areas
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 HK$880
HK$1,343 total
includes taxes & fees
31 Mar - 1 Apr
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 HK$1,389
HK$1,735 total
includes taxes & fees
30 Mar - 31 Mar
The Ellis at Chandler Brook Village
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 HK$1,389
HK$1,735 total
includes taxes & fees
30 Mar - 31 Mar
The Chapman at Chandler Brook Village
1 bedroom, iron/ironing board, travel cot, 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 HK$1,068
HK$1,335 total
includes taxes & fees
30 Mar - 31 Mar
Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES
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 HK$1,150
HK$2,318 total
includes taxes & fees
29 Mar - 30 Mar
Cozy Winter Stay • Nut House • Near Mt & Bridgton
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 HK$1,298
HK$2,949 total
includes taxes & fees
13 Apr - 14 Apr
Lake Front Cabin on Desirable Highland Lake
Smart TV, fireplace, books

Cozy Retreat w/ Fireplace, EV Charger, King Bed

Cozy Retreat w/ Fireplace, EV Charger, King Bed
Bethel
9.2 out of 10, Wonderful, (9 reviews)
"Place was clean, comfy, and in a great location - just as described. Host was responsive and left clear instructions for everything. "
United States
Kevin S.
Cozy Retreat w/ Fireplace, EV Charger, King Bed
Outdoor spa tub

Ski Sunday River, Killer Views, Hot Tub, Epic Game Room, Fire pit, Dog Friendly

Ski Sunday River, Killer Views, Hot Tub, Epic Game Room, Fire pit, Dog Friendly
Newry
10.0 out of 10, Exceptional, (15 reviews)
"We had a great stay! Could not recommend enough, and would love to stay again! "
United States
Brittney C.
The price is HK$909
HK$5,033 total
includes taxes & fees
29 Mar - 30 Mar
Ski Sunday River, Killer Views, Hot Tub, Epic Game Room, Fire pit, Dog Friendly
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 HK$1,949
HK$3,890 total
includes taxes & fees
29 Mar - 30 Mar
Sunnyside home near Sunday River, Black Mountain, Lakes, Rivers and Hikes
Smart TV, fireplace, video games, ping pong

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 HK$1,937
HK$4,849 total
includes taxes & fees
29 Mar - 30 Mar
1 Mile to Sunday River! Hot Tub! Fire Pit! Sleeps 11!
Smart TV, fireplace

Newly Renovated/Furnished Condo, just 3 min to Sunday River!

Newly Renovated/Furnished Condo, just 3 min to Sunday River!
Bethel
10.0 out of 10, Exceptional, (11 reviews)
"Perfect place great host right price "
United States
Darrin S.
Newly Renovated/Furnished Condo, just 3 min to Sunday River!
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 HK$2,739
HK$4,870 total
includes taxes & fees
13 Apr - 14 Apr
Ultra Private, Crooked Reflections, Riverside Retreat, Hot Tub, Waterfront Glass
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 HK$1,565
HK$3,732 total
includes taxes & fees
30 Mar - 31 Mar
Ski-in/out 2-story condo with balcony, on-site indoor pool, hot tub, sauna, W/D
Interior

Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway

Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway
Bridgton
10.0 out of 10, Exceptional, (58 reviews)
"Lovely getaway!"
United States
Victor R.
The price is HK$1,065
HK$2,689 total
includes taxes & fees
8 Apr - 9 Apr
Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway
Outdoor spa tub

Cozy Maine Cabin Escape. Hot Tub Under the Stars. Firepit. Dog Friendly

Cozy Maine Cabin Escape. Hot Tub Under the Stars. Firepit. Dog Friendly
Bethel
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful built cabin with newer amenities that make it very relaxing. Communication was spot on when I had any questions. Wonderful stay"
United States
Justen G.
Cozy Maine Cabin Escape. Hot Tub Under the Stars. Firepit. Dog Friendly
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, (5 reviews)
"The condo was very neat and clean. It was exactly what we were looking for."
United States
Amy
The price is HK$978
HK$3,000 total
includes taxes & fees
31 Mar - 1 Apr
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

Oxford Casino Hotel

Oxford Casino Hotel

2/10 Terrible
"Our room was dirty, there was a bandaid on the floor and the coffee maker was disgusting. "
Benjamin 3-night trip
Posted 4 hours ago
Oxford Casino Hotel

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
  • Use the map to find apartments and other holiday homes in the Greenwood neighbourhood you prefer
  • 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 holiday rental in Greenwood?

Yes, there are holiday rentals close to the most popular sights in Greenwood, or you can select a more secluded option if you're looking for a relaxing stay. Greenwood is known for its ski areas.

What are some of the best holiday rentals that Greenwood has to offer?

Luxury Lakefront Estate on 155 Acres - Pickleball, Reunions & Weddings: This holiday home rental outside of Greenwood is located on a lake, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a library and 1 hot tub.

How many holiday rentals will I find in Greenwood?

With 21 Expedia holiday rentals, you're guaranteed 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 holiday rental in Greenwood like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Greenwood. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a small group gathering.