Greenwood Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Greenwood vacation rentals

Property grounds

Cabin in Maine Woods-The Beech

Cabin in Maine Woods-The Beech
Stoneham
10.0 out of 10, Exceptional, (2 reviews)
"I planned this trip for my birthday, and it was absolutely what I was hoping for. The people running the place were beyond kind and helpful, and went out of their way to make sure we were comfortable/happy. The cabin was exactly as portrayed, if not better. "
United States
joss r.
The price is ￥11,961
￥22,096 total
includes taxes & fees
May 5 - May 6
Cabin in Maine Woods-The Beech
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 ￥19,807
￥32,715 total
includes taxes & fees
May 6 - May 7
An Authentic Clean & Cozy Maine Homestay
Property grounds

Manor Suite,cozy newly renovated,downtown & beach

Manor Suite,cozy newly renovated,downtown & beach
Bridgton
10.0 out of 10, Exceptional, (1 review)
"Property was very clean! it had everything you needed right there! "
United States
Lisa
The price is ￥13,036
￥25,525 total
includes taxes & fees
Apr 30 - May 1
Manor Suite,cozy newly renovated,downtown & beach
Terrace/patio

Cabin in Maine Woods-The Bogey

Cabin in Maine Woods-The Bogey
Stoneham
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property, beautiful cabin, just a perfect couple days of quiet, will definitely be back "
United States
Scott C.
The price is ￥11,961
￥22,096 total
includes taxes & fees
May 5 - May 6
Cabin in Maine Woods-The Bogey
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 ￥14,353
￥21,630 total
includes taxes & fees
May 5 - May 6
Unique lodging in the wilderness. Off the grid location great place to disconnect and enjoy nature. Access via foot or other in wintertime.
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 ￥21,784
￥96,860 total
includes taxes & fees
May 6 - May 7
Nature Retreat, Sauna, Hot Tub, Gameroom, Fire Pit
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, (13 reviews)
"Perfect place great host right price "
United States
Darrin S.
Newly Renovated/Furnished Condo, just 3 min to Sunday River!
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, (90 reviews)
"Great place to stay."
United States
Sara K.
The price is ￥18,516
￥36,749 total
includes taxes & fees
Apr 28 - Apr 29
Charming Home Near Sunday River & Other Ski Areas
Property grounds

Maine Woods Treehouse-The Birdie

Maine Woods Treehouse-The Birdie
Stoneham
9.4 out of 10, Exceptional, (6 reviews)
"Great little (big) tree house in the woods. Great spot to wake up"
United States
James D.
The price is ￥15,789
￥29,008 total
includes taxes & fees
May 7 - May 8
Maine Woods Treehouse-The Birdie
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 ￥17,942
￥27,380 total
includes taxes & fees
May 7 - May 8
Adult Themed get-a-way! Centrally located to ski mountains, Oxford Casino, OPS.
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 ￥23,037
￥58,073 total
includes taxes & fees
Apr 26 - Apr 27
Lake Front Cabin on Desirable Highland Lake
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, (16 reviews)
"We had a great stay! Could not recommend enough, and would love to stay again! "
United States
Brittney C.
The price is ￥22,998
￥117,158 total
includes taxes & fees
Apr 27 - Apr 28
Ski Sunday River, Killer Views, Hot Tub, Epic Game Room, Fire pit, Dog Friendly
Interior

The Ellis at Chandler Brook Village

The Ellis at Chandler Brook Village
Bethel
10.0 out of 10, Exceptional, (16 reviews)
"The place was clean and adorable! We had a great time and had everything we needed!"
United States
Ellen B.
The price is ￥28,300
￥35,019 total
includes taxes & fees
May 5 - May 6
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 ￥27,909
￥64,318 total
includes taxes & fees
Apr 26 - Apr 27
Sunnyside home near Sunday River, Black Mountain, Lakes, Rivers and Hikes
1 bedroom, iron/ironing board, travel crib, free WiFi

Barn on Pleasant-walk to Highland beach & town

Barn on Pleasant-walk to Highland beach & town
Bridgton
10.0 out of 10, Exceptional, (22 reviews)
"Absolutely beautiful place to stay! The room was very welcoming and cozy. "
United States
Robyn N.
The price is ￥25,118
￥30,856 total
includes taxes & fees
Apr 26 - Apr 27
Barn on Pleasant-walk to Highland beach & town
TV

Sunday River Condo - Cherry Lane

Sunday River Condo - Cherry Lane
Bethel
10.0 out of 10, Exceptional, (6 reviews)
"Convenient location, very clean and cozy condo"
United States
Olga S.
The price is ￥16,913
￥42,701 total
includes taxes & fees
Apr 25 - Apr 26
Sunday River Condo - Cherry Lane
Interior

The Swift at Chandler Brook Village

The Swift at Chandler Brook Village
Bethel
10.0 out of 10, Exceptional, (4 reviews)
"We had a great time staying in the yurts. We were traveling with another couple and we were able to get yurts next to one another making it easier to hang out together. We definitely took advantage of the fire pit outside. I would absolutely recommend this place! "
United States
Mandy P.
The price is ￥28,300
￥35,367 total
includes taxes & fees
Apr 27 - Apr 28
The Swift at Chandler Brook Village
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 ￥19,138
￥38,591 total
includes taxes & fees
May 5 - May 6
Historic, luxurious 2 bed 2 bath private suite in Lovell, 10 mins to Kezar 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.
The price is ￥13,396
￥32,680 total
includes taxes & fees
Apr 26 - Apr 27
Cozy Retreat w/ Fireplace, EV Charger, King Bed
Private kitchen

Cozy townhome with 1 bedroom and WiFi in tranquil Bethel, close to Sunday River

Cozy townhome with 1 bedroom and WiFi in tranquil Bethel, close to Sunday River
Bethel
9.6 out of 10, Exceptional, (5 reviews)
"Great location and property. Check in at the hotel was easy. Pet friendly!"
United States
Kevin L.
The price is ￥29,998
￥47,300 total
includes taxes & fees
Apr 25 - Apr 26
Cozy townhome with 1 bedroom and WiFi in tranquil Bethel, close to Sunday River
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Greenwood Hotel Reviews

Highland Lake Resort

Highland Lake Resort

10/10 Excellent
"Stayed during the off season so we didn’t get to enjoy all the resort offers due to weather. The room was clean and offered a nice view of the lake. The staff was very friendly and accommodating. Their newly opened banquet room is beautiful. "
Sheila 1-night trip
Posted 8 hours ago
Highland Lake Resort

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 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?

INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space: Visitors like this Greenwood vacation home rental. It is located on a river and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Greenwood?

With 20 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.