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Holiday Rentals in Greenwood

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Holiday Rentals in Greenwood

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

10.0 out of 10, Exceptional, (325)
"House was great for what we needed. Everyone had a great time staying there. View was unbelievable. Short distance from Sunday River. "
The Artist's Cabin at Powder Ridge Overlooking Sunday River SKI PARKING PASS

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

10.0 out of 10, Exceptional, (58)
"We stayed as a large group for the 3rd year in a row and we have nothing but amazing things to say. The pool is great and the yard is large enough to have multiple activities at once. Can’t wait for next year!"
INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space

Lakefront Cottage: Boat Dock, Patio & Kayaks!

3.0 star property
Lakefront Cottage: Boat Dock, Patio & Kayaks!

Lakefront Log Home 12 feet Away from Lake

10.0 out of 10, Exceptional, (60)
"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 €454
includes taxes & fees
1 Nov - 2 Nov
Lakefront Log Home 12 feet Away from Lake

Cabin in Maine Woods-The Bogey

10.0 out of 10, Exceptional, (1)
"Beautiful property, beautiful cabin, just a perfect couple days of quiet, will definitely be back "
The price is €122
includes taxes & fees
7 Oct - 8 Oct
Cabin in Maine Woods-The Bogey

Lakefront, Near Sunday River, Steam Rm, Firepit, HUGE Kitchen, LG Fireplace

9.4 out of 10, Exceptional, (48)
"It was overall an amazing stay. Everything was perfect."
Lakefront, Near Sunday River, Steam Rm, Firepit, HUGE Kitchen, LG Fireplace

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

8.8 out of 10, Excellent, (41)
"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

LEAF PEEPER DEALS PRIVATE HOME,SLEEPS 12, GRAND VIEWS & HOT TUB & PET FRIENDLY

9.6 out of 10, Exceptional, (60)
"beautiful house, great location, a must stay"
LEAF PEEPER DEALS PRIVATE HOME,SLEEPS 12, GRAND VIEWS & HOT TUB & PET FRIENDLY

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

9.8 out of 10, Exceptional, (49)
"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

Maine Woods Treehouse-The Birdie

9.6 out of 10, Exceptional, (4)
"Very casual about check in they live next to the main Office and have kids so may be next door. Just key the radio on counter. We got there early and were given a good fishing place to try out before we came back. The last day we got directions to a local lake that is a short walk down a logging road. Like having a whole valley with a lake in the middle to yourself. We didn’t see a soul the whole time and it’s a good size lake. The description about out being off grid is dead on, 12 bolt lights...
The price is €159
includes taxes & fees
7 Oct - 8 Oct
Maine Woods Treehouse-The Birdie

The Mansion- Exclusive Private Estate on 5 Pristine Acres

10.0 out of 10, Exceptional, (41)
"Outstanding location close to hiking, golf, fishing, etc. Nice private setting with plenty of space for a big group to spread out. Lots of fun games and activities on site. Great amenities and excellent communication throughout the process. "
The Mansion- Exclusive Private Estate on 5 Pristine Acres

9 Bdrm Premiere Luxury Estate Sleep 26 Movie Theater, Pool,Spa,Game Rm,Steam Rms

10.0 out of 10, Exceptional, (4)
"We brought our sons, their wives and children as a Christmas present. The place was perfect. It was clean and the kitchen was fully stocked. We spent many hours in the movie theater watching NFL Divisional games on Sat & Sunday. Great place building memories and it was as advertised. "
9 Bdrm Premiere Luxury Estate Sleep 26 Movie Theater, Pool,Spa,Game Rm,Steam Rms

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

10.0 out of 10, Exceptional, (35)
"Wonderful stay at The Bear’s Den. Great property with plenty of amenities and things to do! Great for families with kids. "
Welcome to The Bear's Den! Dog friendly and 5 minutes to Pleasant Mountain!

Swim, Kayak, lawn games. Walk to ice cream. Live Theatre , firepit smores!

10.0 out of 10, Exceptional, (97)
"Stunning property and wonderful hosts - 110% appointed and their thoughtful and personal touches make it feel like home!"
Swim, Kayak, lawn games. Walk to ice cream. Live Theatre , firepit smores!

New.Minutes from Slopes.Firepit.2-Fireplaces.Hot Tub.Sauna.Rec Room.Bunk Room

10.0 out of 10, Exceptional, (7)
"We had a great time at a great house. Thanks so much!!!"
The price is €694
includes taxes & fees
8 Oct - 9 Oct
New.Minutes from Slopes.Firepit.2-Fireplaces.Hot Tub.Sauna.Rec Room.Bunk Room

Cabin between Two Lakes -Private Beach on Moose Pond Minutes to Pleasant Mt Ski

10.0 out of 10, Exceptional, (27)
"Wonderful house in a convenient, quiet location! Perfect for skiing at Pleasant Mountain. "
Cabin between Two Lakes -Private Beach on Moose Pond Minutes to Pleasant Mt Ski

*NEW* Luxury A-Frame by Sunday River w/ hot tub

10.0 out of 10, Exceptional, (13)
"Amazing property and great location!"
*NEW* Luxury A-Frame by Sunday River w/ hot tub

Lakes & Mountain Experience! 4 Seasons Getaway -- 3 Bed Cozy Cabin

10.0 out of 10, Exceptional, (23)
"Everything was very clean, communication was fast and friendly, location was excellent, and we all had a great stay."
Lakes & Mountain Experience! 4 Seasons Getaway -- 3 Bed Cozy Cabin

9 Bedroom Estate, Sleeps 24, Heated Pool, Hot Tub, Movie Theater, Game Room

10.0 out of 10, Exceptional, (32)
"Had a great time in the mountains. Beds were comfy and pool/hot tub was great!"
9 Bedroom Estate, Sleeps 24, Heated Pool, Hot Tub, Movie Theater, Game Room

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

10.0 out of 10, Exceptional, (13)
"We had the best time ever at this property. Swimming, fishing, dinners on the deck at Sunset PRICELESS!!!"
Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views
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 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, apart-hotels, 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 favorite 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 depends 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 €122 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 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?

INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space: This holiday home rental outside of Greenwood is located on a river, and has an outdoor pool, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Greenwood?

With 22 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 Papoose Pond. While here, Mt. Abram and Tucker's Tumble Glades 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.