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Greenwood Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Greenwood

3 bedrooms, desk, iron/ironing board, free WiFi
An Authentic Clean & Cozy Maine Homestay

Vacation Home in Buckfield

9.8 out of 10, Exceptional, (64)
"The host provided excellent information and was very easy to communicate with. The property was very comfortable and clean. "
United States
Meg
$188 nightly
The price is $205
Dec 8 - Dec 9
Total with taxes and fees
An Authentic Clean & Cozy Maine Homestay
Bar (on property)
Adult Themed get-a-way! Centrally located to ski mountains, Oxford Casino, OPS.

Apartment in South Paris

8.4 out of 10, Very Good, (22)
"We enjoyed our stay. We had a wedding and this place was only ten minutes away from the venue. Plenty of stores and restaurants. The property was very clean and we were very comfortable there!"
United States
Anonymous traveler
$158 nightly
The price is $172
Dec 7 - Dec 8
Total with taxes and fees
Adult Themed get-a-way! Centrally located to ski mountains, Oxford Casino, OPS.
Exterior
Nature Retreat, Sauna, Hot Tub, Gameroom, Fire Pit

Chalet in Woodstock

2.0 star property
$626 nightly
The price is $682
Dec 15 - Dec 16
Total with taxes and fees
Nature Retreat, Sauna, Hot Tub, Gameroom, Fire Pit
Exterior
Sunday River 5 Min! Family / Group / Couples Retreat!

Vacation Home in Newry

10.0 out of 10, Exceptional, (2)
"I would suggest specifying that the coffee maker is a Keurig"
United States
Maggie C.
$501 nightly
The price is $546
Dec 8 - Dec 9
Total with taxes and fees
Sunday River 5 Min! Family / Group / Couples Retreat!
Property grounds
Manor Suite,cozy newly renovated,downtown & beach

Vacation Home in Bridgton

10.0 out of 10, Exceptional, (1)
"Property was very clean! it had everything you needed right there! "
United States
Lisa
$131 nightly
The price is $142
Dec 9 - Dec 10
Total with taxes and fees
Manor Suite,cozy newly renovated,downtown & beach
Smart TV, fireplace
Newly Renovated/Furnished Condo, just 3 min to Sunday River!

Apartment in Bethel

10.0 out of 10, Exceptional, (11)
"Perfect for our needs"
United States
Daniel
$235 nightly
The price is $247
Dec 8 - Dec 9
Total with taxes and fees
Newly Renovated/Furnished Condo, just 3 min to Sunday River!
Terrace/patio
The Pleasant at Chandler Brook Village

Vacation Home in Bethel

9.8 out of 10, Exceptional, (7)
"This was a fun place to stay. Facilities and Yurt were well kept and accomodating."
United States
Erin G.
$202 nightly
The price is $221
Dec 8 - Dec 9
Total with taxes and fees
The Pleasant at Chandler Brook Village
2 bedrooms, desk, WiFi, bed sheets
Historic, luxurious 2 bed 2 bath private suite in Lovell, 10 mins to Kezar Lake

Aparthotel in Lovell

10.0 out of 10, Exceptional, (5)
"Very nice stay. Perfect for a couple of adults. "
United States
Joann M.
$240 nightly
The price is $262
Dec 24 - Dec 25
Total with taxes and fees
Historic, luxurious 2 bed 2 bath private suite in Lovell, 10 mins to Kezar Lake
Fridge, microwave, oven, stovetop
NEW Chalet 6 minutes from Sunday River! Hot tub, Sauna, Sleeps 12, Dog Friendly!

Chalet in Bethel

10.0 out of 10, Exceptional, (9)
"Great location, great amenities "
United States
Cory S.
$598 nightly
The price is $651
Dec 8 - Dec 9
Total with taxes and fees
NEW Chalet 6 minutes from Sunday River! Hot tub, Sauna, Sleeps 12, Dog Friendly!
1 bedroom, free WiFi, bed sheets
Slope Side Retreat! HotTub| Sauna| Pool! Sleeps 6

Condo in Newry

10.0 out of 10, Exceptional, (3)
"The condo was very neat and clean. It was exactly what we were looking for."
United States
Amy
Slope Side Retreat! HotTub| Sauna| Pool! Sleeps 6
Smart TV, fireplace, DVD player, foosball
Charming Home Near Sunday River & Other Ski Areas

Vacation Home in Rumford

9.8 out of 10, Exceptional, (79)
"Great place to stay."
United States
Sara K.
$209 nightly
The price is $228
Dec 8 - Dec 9
Total with taxes and fees
Charming Home Near Sunday River & Other Ski Areas
Exterior
Dog Friendly/Mt. Home/Beau Views/ 3 or more nights 20% DISC!

Chalet in Bryant Pond

10.0 out of 10, Exceptional, (51)
"We had a great stay in Bryant Pond. Lots of outdoor activities in the area. "
United States
Nicholas W.
$569 nightly
The price is $593
Dec 6 - Dec 7
Total with taxes and fees
Dog Friendly/Mt. Home/Beau Views/ 3 or more nights 20% DISC!
Property grounds
Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES

Condo in Bridgton

10.0 out of 10, Exceptional, (18)
"Stay was great, as advertised."
United States
Mary Campbell K.
$157 nightly
The price is $171
Dec 7 - Dec 8
Total with taxes and fees
Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES
Fridge, microwave, oven, stovetop
Sunday River Condo - Cherry Lane

Apartment in Bethel

10.0 out of 10, Exceptional, (6)
"Loved the condo, easy access, no issues, bed was comfy, couch was comfy to sit on. Just loves our over all stay"
United States
Debra H.
Sunday River Condo - Cherry Lane
Fridge, microwave, oven, stovetop
12min Sunday River! Hot Tub, Pet Friendly, Firepit

Chalet in Bethel

8.8 out of 10, Excellent, (3)
"Great house and location in the woods on a private dirt road. House is very comfortable and the dogs enjoyed the walks on the dirt road too. We would stay here again. "
United States
Silvia D.
$437 nightly
The price is $476
Dec 8 - Dec 9
Total with taxes and fees
12min Sunday River! Hot Tub, Pet Friendly, Firepit
Terrace/patio
The Swift at Chandler Brook Village

Vacation Home in Bethel

10.0 out of 10, Exceptional, (4)
"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.
$202 nightly
The price is $221
Dec 8 - Dec 9
Total with taxes and fees
The Swift at Chandler Brook Village
Private kitchen
Pet friendly 2-bedroom house near downtown Bethel

Vacation Home in Bethel

8.0 out of 10, Very Good, (1)
$371 nightly
The price is $404
Dec 14 - Dec 15
Total with taxes and fees
Pet friendly 2-bedroom house near downtown Bethel
Terrace/patio
Adventure&Wellness ~Hot Tub ~Sauna ~Theater ~Boot Room ~15min to Sunday River

Cabin in Bethel

10.0 out of 10, Exceptional, (1)
"Amazing stay! 5 Stars without hesitationWe honestly didn’t want to leave a review because we wanted this gem of a place to be our secret! To many great reviews, prices go up and hard to to book in the future! But we couldn’t do that to our host Travis who was so friendly and communicative from the time of inquiry to checkout making our stay enjoyable and stress-free. The property is just as stunning in person as it is in the photos and is absolutely immaculate. Ridgeline Retreat was in fact just...
United States
Christina L.
$557 nightly
The price is $607
Dec 9 - Dec 10
Total with taxes and fees
Adventure&Wellness ~Hot Tub ~Sauna ~Theater ~Boot Room ~15min to Sunday River
Outdoor spa tub
New.Minutes from Slopes.Firepit.2-Fireplaces.Hot Tub.Sauna.Rec Room.Bunk Room

Chalet in Newry

10.0 out of 10, Exceptional, (7)
"We had a great time at a great house. Thanks so much!!!"
United States
Henry C.
$729 nightly
The price is $794
Dec 7 - Dec 8
Total with taxes and fees
New.Minutes from Slopes.Firepit.2-Fireplaces.Hot Tub.Sauna.Rec Room.Bunk Room
Smart TV, fireplace, books
Cozy Retreat w/ Fireplace, EV Charger, King Bed

Vacation Home in Bethel

9.2 out of 10, Wonderful, (7)
"Beautiful space "
United States
Abigail S.
$188 nightly
The price is $205
Dec 8 - Dec 9
Total with taxes and fees
Cozy Retreat w/ Fireplace, EV Charger, King Bed
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

Jordan Hotel

Jordan Hotel

10/10 Excellent
"All"
Melissa 2-night trip
Posted 2 days ago
Jordan Hotel

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Greenwood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $275 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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 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 Snow Falls. 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.