Greenwood Holiday Rentals

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Our top choices for Greenwood holiday rentals

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 AU$284
includes taxes & fees
20 Apr - 21 Apr
An Authentic Clean & Cozy Maine Homestay

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 AU$192
includes taxes & fees
18 Apr - 19 Apr
Unique lodging in the wilderness. Off the grid location great place to disconnect and enjoy nature. Access via foot or other in wintertime.

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 AU$230
includes taxes & fees
3 May - 4 May
Manor Suite,cozy newly renovated,downtown & beach

Fall fun in Oxford Hills

Fall fun in Oxford Hills
Sumner
10.0 out of 10, Exceptional, (27 reviews)
"We enjoyed the location and cabin very much!"
United States
Stephanie M.
Fall fun in Oxford Hills

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 AU$196
includes taxes & fees
3 May - 4 May
Cabin in Maine Woods-The Beech

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, (12 reviews)
"Perfect place great host right price "
United States
Darrin S.
The price is AU$332
includes taxes & fees
17 Apr - 18 Apr
Newly Renovated/Furnished Condo, just 3 min to Sunday River!

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 AU$242
includes taxes & fees
19 Apr - 20 Apr
Adult Themed get-a-way! Centrally located to ski mountains, Oxford Casino, OPS.

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

Nature Retreat, Sauna, Hot Tub, Gameroom, Fire Pit
Woodstock
The price is AU$851
includes taxes & fees
28 Apr - 29 Apr
Nature Retreat, Sauna, Hot Tub, Gameroom, Fire Pit

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 AU$196
includes taxes & fees
12 May - 13 May
Cabin in Maine Woods-The Bogey

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 AU$1,206
includes taxes & fees
19 Apr - 20 Apr
Ski Sunday River, Killer Views, Hot Tub, Epic Game Room, Fire pit, Dog Friendly

The Ellis at Chandler Brook Village

The Ellis at Chandler Brook Village
Bethel
10.0 out of 10, Exceptional, (16 reviews)
"Our Yurt was clean and quiet and was an exceptional first time experience , I would definitely recommend . "
United States
Richard S.
The price is AU$306
includes taxes & fees
21 Apr - 22 Apr
The Ellis at Chandler Brook Village

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 AU$316
includes taxes & fees
21 Apr - 22 Apr
Cozy Retreat w/ Fireplace, EV Charger, King Bed

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

Ski-In/Out Condo with HotTub Sauna & Pool Sleeps 6
Newry
9.2 out of 10, Wonderful, (7 reviews)
"The condo was very neat and clean. It was exactly what we were looking for."
United States
Amy
Ski-In/Out Condo with HotTub Sauna & Pool Sleeps 6

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 AU$253
includes taxes & fees
3 May - 4 May
Maine Woods Treehouse-The Birdie

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 AU$570
includes taxes & fees
17 Apr - 18 Apr
Lake Front Cabin on Desirable Highland Lake

Dream Lakefront Modern Cabin

Dream Lakefront Modern Cabin
West Bridgton
10.0 out of 10, Exceptional, (11 reviews)
"This was a beautiful property! Very clean and relaxing! "
United States
Mary G.
Dream Lakefront Modern Cabin

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)
"My wife and I enjoyed our stay very much and it exceeded our expectations. Very clean and comfortable. Would definitely stay here again and have already told friends about it."
United States
Tom L.
The price is AU$273
includes taxes & fees
30 Apr - 1 May
Barn on Pleasant-walk to Highland beach & town

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 AU$306
includes taxes & fees
20 Apr - 21 Apr
The Swift at Chandler Brook Village

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 AU$340
includes taxes & fees
20 Apr - 21 Apr
Historic, luxurious 2 bed 2 bath private suite in Lovell, 10 mins to Kezar Lake

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)
"The owner instantly responded to me with my questions."
United States
Mario G.
The price is AU$343
includes taxes & fees
23 Apr - 24 Apr
Charming Home Near Sunday River & Other Ski Areas
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

Find out more about Greenwood

Everything you need to know about Greenwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Greenwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greenwood holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Greenwood holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greenwood. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Greenwood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greenwood holiday rentals we have selected for you start as low as AU$242 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Greenwood rentals

At Expedia, we put the best Greenwood holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Greenwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greenwood holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greenwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 20 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.