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Greenwood Vacation Rentals

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Vacation Rentals in Greenwood

Our top choices for Greenwood vacation rentals

Abundant Light with Hot Tub, King Bed, and Wood stove-18 Minutes to Sunday River

10.0 out of 10, Exceptional, (26)
"Cozy cabin close to Sunday River and right near the town. Would stay again."
Abundant Light with Hot Tub, King Bed, and Wood stove-18 Minutes to Sunday River

INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space

10.0 out of 10, Exceptional, (56)
"This house was a blast - would def stay again"
INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space

Secluded dog-friendly getaway with hot tub, game room, firepit, mountain views

8.8 out of 10, Excellent, (40)
"Great views and location if you are looking for a part of Maine not super coastal and touristy."
Secluded dog-friendly getaway with hot tub, game room, firepit, mountain views

Lakefront Log Home 12 feet Away from Lake

10.0 out of 10, Exceptional, (57)
"Incredible night away on a quiet Maine pond. Highly recommended, Todd was great and the place was perfect! We will be back for sure."
The price is CA $519
CA $774 total
includes taxes & fees
Sep 7 - Sep 8
Lakefront Log Home 12 feet Away from Lake

Rediker Retreat- Authentic Riverfront Luxury Log Home

10.0 out of 10, Exceptional, (91)
"Great stay, awesome house"
Rediker Retreat- Authentic Riverfront Luxury Log Home

The Artist's Cabin at Powder Ridge Overlooking Sunday River SKI PARKING PASS

10.0 out of 10, Exceptional, (324)
"Great place!"
The Artist's Cabin at Powder Ridge Overlooking Sunday River SKI PARKING PASS

Lovely, Lake Front 2-Bedroom Cabin with Porch and Dock on Saturday Pond

10.0 out of 10, Exceptional, (6)
Lovely, Lake Front 2-Bedroom Cabin with Porch and Dock on Saturday Pond

Million-Dollar View: Waterfront Cabin in Bridgton!

9.0 out of 10, Wonderful, (2)
"Everything I and my family hoped for. "
Million-Dollar View: Waterfront Cabin in Bridgton!

Condo at Pleasant Mountain

9.8 out of 10, Exceptional, (20)
"Loved this property, will book again."
Condo at Pleasant Mountain

Lakefront home with lovely lake views - one mile from the casino

9.8 out of 10, Exceptional, (46)
"Really enjoyed the location and charm of the place. It has the rustic feel of a cabin with all the modern amenities for a comfortable stay."
Lakefront home with lovely lake views - one mile from the casino

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

10.0 out of 10, Exceptional, (15)
"Our stay was amazing.. close to town, very comfortable and met all of our needs.. would definitely stay there again!"
The price is CA $216
CA $266 total
includes taxes & fees
Sep 2 - Sep 3
Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES

Lakeside house with a separate bunkhouse

8.2 out of 10, Very good, (10)
"We enjoyed our stay here. Clean and comfortable house in a great location."
Lakeside house with a separate bunkhouse

Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views

10.0 out of 10, Exceptional, (11)
"We loved the house. It was very clean and the view was incredible! Can’t wait to go back!"
Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views

Cozy log cabin home. 5 minutes to the beach, pet and family friendly home.

2.0 out of 10, (1)
Cozy log cabin home. 5 minutes to the beach, pet and family friendly home.

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

10.0 out of 10, Exceptional, (33)
"Sindi and Doug were excellent hosts! The property was extremely clean, welcoming and full stocked with everything needed for a ski weekend!"
Welcome to The Bear's Den! Dog friendly and 5 minutes to Pleasant Mountain!

Highland Dream: Summer Paradise! 5BR/2BA W Sandy Beach, Stay and Play. 4 Seasons

10.0 out of 10, Exceptional, (24)
"Great location , plenty of room for a large family or group."
The price is CA $742
CA $1,438 total
includes taxes & fees
Sep 14 - Sep 15
Highland Dream: Summer Paradise! 5BR/2BA W Sandy Beach, Stay and Play. 4 Seasons

Adorable cottage set among tall pines with sandy beach -only .5 mile from town.

9.8 out of 10, Exceptional, (58)
"We stayed a few days and the town and surroundings were very nice. The lake was clean and not too busy. The cottage was in a great location and had everything you needed."
Adorable cottage set among tall pines with sandy beach -only .5 mile from town.

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

9.4 out of 10, Exceptional, (26)
"Also fun to stay here!"
The price is CA $124
CA $186 total
includes taxes & fees
Sep 2 - Sep 3
Unique lodging in the wilderness. Off the grid location great place to disconnect and enjoy nature. Access via foot or other in wintertime.

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

9.6 out of 10, Exceptional, (16)
"Would stay here again. Loved the location and the size of the rooms! Perfect for a group and very pet friendly."
Expansive Retreat - All-Season Contemporary Farmhouse [Lakes & Mountains]

Waterfront Home on Long Lake

10.0 out of 10, Exceptional, (37)
"Our stay at the waterfront home on Long Lake was fantastic. This was our 2nd year staying at this house and it wont' be our last. "
Waterfront Home on Long Lake
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

Find out more about Greenwood

Everything you need to know about Greenwood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Greenwood vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Greenwood vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Greenwood vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greenwood vacation rentals we have selected for you start as low as CA $124 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Greenwood rentals

At Expedia, we put the best Greenwood vacation 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 vacation.

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 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: You might want to consider this vacation home rental near Greenwood, which 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 22 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 Papoose Pond. While here, Mt. Abram and Tucker's Tumble Glades 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.