Greenwood Vacation Rentals from $135: Search Short-Term Rentals

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Our top choices for Greenwood vacation rentals

A room with a large window, a sofa with patterned cushions, a small table with a vase of flowers, and a radiator.

1. Evergreen Valley Inn by Coolvacay

Stoneham

SHREOSHI

$124 nightly

Nov 10 - Nov 11

Total with taxes and fees

Three Peaks Cabin glowing in a winter wonderland under a pink sunset sky near Sunday River.

2. Sunday River|Mt Views| Dog Friendly|20% Off 3+

Bryant Pond

Michelle L.

$619 nightly

Nov 8 - Nov 9

Total with taxes and fees

A person sitting on a bed in a room with wooden walls and a ceiling, reading a book.

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

Woodstock

$606 nightly

Nov 30 - Dec 1

Total with taxes and fees

A large, two-story house with a covered porch and a stone garden feature.

4. NEW Luxury Retreat Hot Tub+Swim Lake+Firepits

Woodstock

$723 nightly

Nov 5 - Nov 6

Total with taxes and fees

A cozy log cabin interior with a stone fireplace, a comfortable sofa, and a large window offering a view of the outdoors.

5. Ursa Major House - Quiet family getaway, minutes from skiing, hiking, biking.

Bethel

Tanya M.

$616 nightly

Nov 5 - Nov 6

Total with taxes and fees

A spacious living room with a brown leather sofa, a flat-screen TV, and a wooden ceiling.

6. NEW! Modern Getaway - Hot Tub/Fire Pit/Pool table

Norway

Irene S.

$743 nightly

Nov 5 - Nov 6

Total with taxes and fees

A hot tub in a forested area with outdoor seating and a grill.

7. Cedar🏡 Waterfront💦 Hot tub🔥 Pool🎱 Privacy 🕵️

Norway

Colby S.

$618 nightly

Nov 9 - Nov 10

Total with taxes and fees

A spacious wooden interior with a staircase, a dining area, and large windows.

8. Secluded 2BR Log Cabin on 52 Wooded Acres

Norway

$386 nightly

Nov 5 - Nov 6

Total with taxes and fees

A bedroom with a bed, wooden ceiling, a window with blinds, a nightstand, and a framed picture on the wall.

9. An Authentic Clean & Cozy Maine Homestay

Buckfield

Autumn M.

$178 nightly

Nov 6 - Nov 7

Total with taxes and fees

A modern living room with a sectional sofa, a fireplace, and a large window.

10. Unique Family Retreat | HotTub, Fire Pit, Dogs OK!

Bethel

"The rooms looked exactly like the photos, the house was very charming and welcoming feeling. Inside the house, and the hot tub, were clean and in working order. We appreciated all the small touches like soap, showering needs, dish-ware etc. The deck off the main bedroom was a nice little quiet getaway. The property was well taken care of, The fire pit was perfect for the cool nights and s’mores! The hosts were friendly and accommodating. Thanks from, two adults, three teenagers and the dog!"

Abbie C.

$740 nightly

Nov 5 - Nov 6

Total with taxes and fees

A dining table set with plates, cutlery, and a charcuterie board with various cheeses, fruits, and meats.

11. NEW Chalet 6 minutes from Sunday River! Hot tub, Sauna, Sleeps 12, Dog Friendly!

Bethel

Brian D.

$655 nightly

Nov 5 - Nov 6

Total with taxes and fees

A spacious kitchen with a large island, wooden cabinets, and a stone fireplace.

12. Stunning MTN views! Fireplace, Hot Tub, Sleeps 12

Bethel

Jason K.

$766 nightly

Nov 5 - Nov 6

Total with taxes and fees

A rustic interior with a wooden bar, seating area, and a staircase leading to an upper level.

13. Unique Dome with HotTub & Mtn Views

Bryant Pond

Megan O.

$715 nightly

Nov 5 - Nov 6

Total with taxes and fees

A bedroom with a large bed, a fireplace, a hanging chair, and a view of a forest and stream.

14. Ultra Private, Crooked Reflections, Riverside Retreat, Hot Tub, Waterfront Glass

Norway

Elizabeth S.

$728 nightly

Nov 22 - Nov 23

Total with taxes and fees

15. Little Acorn Landing

Norway

phillip D.

$185 nightly

Nov 5 - Nov 6

Total with taxes and fees

A dining area with a wooden table, black chairs, and large windows offering a mountain view.

16. 6BR Mountain Cabin | Hot Tub • Fire Pit

Bethel

Katherine D.

A wooden cabin interior with a dining area, a living room with a sofa, and large windows offering a view of the outdoors.

17. Sleeps 10, Lake View Retreat, with Hot tub & Barrel Sauna

Woodstock

$499 nightly

Nov 5 - Nov 6

Total with taxes and fees

A modern kitchen with a central island, wooden flooring, and large windows.

18. Close to Skiing! HotTub! Game Rm! Sleeps 12!

Bethel

Jolene W.

$855 nightly

Nov 5 - Nov 6

Total with taxes and fees

A room with a large window, a leather armchair, a wooden table, and a small wooden chest.

19. Modern Woodland Retreat • Firepit • Hiking • River

Bethel

wendy b.

$356 nightly

Nov 5 - Nov 6

Total with taxes and fees

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Top Greenwood Hotel Reviews

Hampton Inn Oxford

10/10 Excellent

"Juste super all the way....💓💓💓💓💓💓"

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

10/10 Excellent

"This property was in the most peaceful and private location. House was clean and tastefully decorated. So comfortable with plenty of room . We had a small intimate wedding ceremony with just our immediate family and fur babies. Loved the pool, hot tub, sauna , games and fire pits!! The most perfect place to celebrate any occasion ."

Luxury Lakefront Estate on 138 Acres - Pickleball, Reunions & Weddings

10/10 Excellent

"BOOK IT! If you are considering Moose Lake Ranch for your wedding, vacation, etc DO IT! We cannot thank the team at this property enough. They made everything seem less and better than we could have imagined. We got married 10.10.26 here. We slept about 30 people comfortably. The wedding, thanks to Callie and her team went smoothly. They had everything we asked for and more. The views are stunning and not a single guest wanted to leave."

This woods cabin is a true wilderness getaway. Get ready to commune with nature.

10/10 Excellent

"The cabin was perfect, so secluded and quiet. It was cozy and warm. It had everything we needed for a true retreat camping experience. The hosts were easy to work with and helped shuttle our things up the trek to the cabin too! I would come again"

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 $135 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.

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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?

Luxury Lakefront Estate on 138 Acres - Pickleball, Reunions & Weddings: Visitors like this Greenwood vacation home rental. It is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a library and a hot tub.

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?

Uncle Tom Mountain and Bryant Pond are a couple of lovely local spots to get outside and enjoy nature. 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.

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Check prices for these dates

Our top choices for Greenwood vacation rentals

1. Evergreen Valley Inn by Coolvacay

2. Sunday River|Mt Views| Dog Friendly|20% Off 3+

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

4. NEW Luxury Retreat Hot Tub+Swim Lake+Firepits

5. Ursa Major House - Quiet family getaway, minutes from skiing, hiking, biking.

6. NEW! Modern Getaway - Hot Tub/Fire Pit/Pool table

7. Cedar🏡 Waterfront💦 Hot tub🔥 Pool🎱 Privacy 🕵️

8. Secluded 2BR Log Cabin on 52 Wooded Acres

9. An Authentic Clean & Cozy Maine Homestay

10. Unique Family Retreat | HotTub, Fire Pit, Dogs OK!

11. NEW Chalet 6 minutes from Sunday River! Hot tub, Sauna, Sleeps 12, Dog Friendly!

12. Stunning MTN views! Fireplace, Hot Tub, Sleeps 12

13. Unique Dome with HotTub & Mtn Views

14. Ultra Private, Crooked Reflections, Riverside Retreat, Hot Tub, Waterfront Glass

15. Little Acorn Landing

16. 6BR Mountain Cabin | Hot Tub • Fire Pit

17. Sleeps 10, Lake View Retreat, with Hot tub & Barrel Sauna

18. Close to Skiing! HotTub! Game Rm! Sleeps 12!

19. Modern Woodland Retreat • Firepit • Hiking • River

Find vacation rentals that suit your style

Top Greenwood Hotel Reviews

Hampton Inn Oxford

The Bethel Resort & Suites

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

Luxury Lakefront Estate on 138 Acres - Pickleball, Reunions & Weddings

This woods cabin is a true wilderness getaway. Get ready to commune with nature.

Sleeps 20 | Hot Tub | Game Room | Fire Pit |4500SF

Toddy's camp on the pond

Private Log Cabin with an AMAZING VIREW!!! Hot Tub and Sleeps up to 14

Find out more about Greenwood

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