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

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Our top choices for Greenwood vacation rentals

TV, fireplace, Netflix, streaming services

1. Maine lake front ski getaway!

Greenwood

"Our family had an amazing few days at this beautiful home. The house is adorable and has a beautiful view of the lake. The rear windows really take advantage of the view and made the whole vibe very relaxing. The house was stocked with everything we could need and more. Our group of 6 fit perfectly and the beds were super comfortable! We came to ski and Sunday River was only a short drive away. We also enjoyed some of the local restaurants including the Matterhorn, Sunday River Brewing, Butcher...

lisa c.

2. The Swift Glamping Yurt in Bethel, Maine

Bethel

Mandy P.

$203 nightly

Sep 20 - Sep 21

Total with taxes and fees

3. Modern Woodland Retreat • Firepit • Hiking • River

Bethel

$347 nightly

Sep 22 - Sep 23

Total with taxes and fees

1 bedroom, iron/ironing board, WiFi, bed sheets

4. Adult Themed get-a-way! Centrally located to ski mountains, Oxford Casino, OPS.

South Paris

Sheryl M.

$158 nightly

Sep 20 - Sep 21

Total with taxes and fees

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

Waterford

$124 nightly

Sep 20 - Sep 21

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

6. Cozy Home 8 Mins to Sunday River w/ EV Charger

Bethel

Kristina R.

$223 nightly

Sep 23 - Sep 24

Total with taxes and fees

Apartment, Ensuite (St Moritz) | Hypo-allergenic bedding available, bed sheets

7. Evergreen Valley Inn by Coolvacay

Stoneham

Terry

$124 nightly

Oct 13 - Oct 14

Total with taxes and fees

8. Sunday River Condo Near Ski Lifts, Breweries & Downtown Bethel

Bethel

Matthew B.

$227 nightly

Sep 30 - Oct 1

Total with taxes and fees

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Top Greenwood Hotel Reviews

Highland Lake Resort

10/10 Excellent

"This property was absolutely beautiful. We enjoyed time on the swing down by the lake and just having a cup of coffee on the back porch of our room overlooking the grounds and the water. The room was spacious and the bed was comfy-we would absolutely stay here again."

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

8/10 Good

"Overall a grand house and property and has more places to sleep than it seems in the pictures. There are additional mattresses throughout in closets. We were the first wedding to use the on site tent and storage items, although I was not aware I would be the first. I was talked out of my initial tent rental through an outside company as I had booked that before a permanent tent was added to the property. The tent on site is huge and there are plenty of tables and chairs supplied. There were definitely some kinks to be worked out as those specific offerings are new to them. We had to fix the lighting before use and the generator did not give off as much power as expected. The cost is high for a self-service experience, but as are most wedding venues. The place was mostly clean, but small items like glass doors and bathroom mirrors were noticeably dirty. Many stays appear to be same day change, as when we arrived at 4:00 the cleaners were still finishing up due to a late checkout. Cleaners were very kind, they just have a huge house to get through in a short time. The fire pit is a great area and the deck has a lot of good seating areas. Hot tub is huge. Kitchen is also huge - well stocked. A great place to stay if you have a large group. Floating dock and little fishing boat are a cool addition. Sound system in the house is another cool factor, appeared to have a camera aimed at it. A lot of responsibility on the guest to stay at such a large property."

Lake Cabin | Fire Pit | Direct Lake Access | Pool | Near Ski Area

10/10 Excellent

"We’ve stayed at many different KHA properties throughout our summers in Bridgton and this house was one of our favorites. Our kids loved the dock and we loved having dinners each night on the beautiful deck. It was everything we needed for our vacation! We would definitely stay at Moosin Around again."

Stunning views, luxurious home, heated pool, hot tub, games

10/10 Excellent

"Amazing views and wonderful property. Everything was as advertised! Amenities are all in top notch condition. The pool and spa are super clean and inviting. We are rebooking for next year. This property is 100% worth the trip"

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.

Greenwood Vacation Rentals

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Our top choices for Greenwood vacation rentals

1. Maine lake front ski getaway!

2. The Swift Glamping Yurt in Bethel, Maine

3. Modern Woodland Retreat • Firepit • Hiking • River

4. Adult Themed get-a-way! Centrally located to ski mountains, Oxford Casino, OPS.

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

6. Cozy Home 8 Mins to Sunday River w/ EV Charger

7. Evergreen Valley Inn by Coolvacay

8. Sunday River Condo Near Ski Lifts, Breweries & Downtown Bethel

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

10. 1 bedroom cottage with queen bed and 2 person whirlpool tub.

11. Cozy Retreat w/ Fireplace, EV Charger, King Bed

12. The Bear Glamping Yurt in Bethel, Maine

13. An Authentic Clean & Cozy Maine Homestay

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

15. Little Acorn Landing

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

17. The Rangeley Glamping Yurt in Bethel, Maine

18. Mountain View Chalet with Hot Tub and Game Room

19. Manor Suite,cozy newly renovated,downtown & beach

20. Charming Home Near Sunday River & Other Ski Areas

Find vacation rentals that suit your style

Top Greenwood Hotel Reviews

Highland Lake Resort

Find out more about Greenwood

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