Holiday Rentals Greenwood from £91: Find Short-Term Rentals & Holiday Accommodations

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Our top choices for Greenwood holiday rentals

1. Treehouse With Hot Tub Close to Sunday River!

Woodstock

Fred W.

includes taxes & fees

6 Oct - 7 Oct

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

Bryant Pond

Carson B.

includes taxes & fees

19 Oct - 20 Oct

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

3. Evergreen Valley Inn by Coolvacay

Stoneham

Terry

includes taxes & fees

13 Oct - 14 Oct

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

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

Woodstock

includes taxes & fees

25 Oct - 26 Oct

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

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

Norway

Colby S.

includes taxes & fees

1 Oct - 2 Oct

A modern kitchen with dark cabinetry, a central island, pendant lighting, and a large window.

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

Woodstock

includes taxes & fees

28 Sept - 29 Sept

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

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

Bethel

Tanya M.

includes taxes & fees

27 Sept - 28 Sept

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

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

Norway

Elizabeth S.

includes taxes & fees

28 Sept - 29 Sept

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

9. 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.

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

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

Bethel

Jason K.

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

11. Sunday River Getaway | Sleeps 6 | Pet-Friendly

Bethel

includes taxes & fees

28 Sept - 29 Sept

A bedroom with a bed, a wooden staircase leading to a bathtub, and a wall-mounted heater.

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

South Paris

Sheryl M.

includes taxes & fees

5 Oct - 6 Oct

A yurt interior with a central wooden beam structure, a sofa, a small table, and a television.

13. The Swift Glamping Yurt in Bethel, Maine

Bethel

Mandy P.

includes taxes & fees

19 Oct - 20 Oct

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

14. An Authentic Clean & Cozy Maine Homestay

Buckfield

Meagan D.

includes taxes & fees

28 Sept - 29 Sept

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

15. Unique Dome with HotTub & Mtn Views

Bryant Pond

Beth S.

A spacious living room with a high ceiling and large windows, furnished with leather sofas and a coffee table.

16. POOL+HotTub+Sauna / Privacy+9miles to Sunday River

Bethel

Anonymous traveller

includes taxes & fees

27 Sept - 28 Sept

A yurt with a wooden ceiling, a central light fixture, a sofa, a coffee table, and a kitchen area with a stove.

17. The Bear Glamping Yurt in Bethel, Maine

Bethel

Mustafa

includes taxes & fees

19 Oct - 20 Oct

A kitchen with wooden cabinets, a white refrigerator, a stove, and a window with a view of trees.

18. SUNDAY RIVER RENTAL

Bethel

Samantha M.

includes taxes & fees

30 Sept - 1 Oct

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

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

Bethel

Brian D.

includes taxes & fees

29 Sept - 30 Sept

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Top Greenwood Hotel Reviews

Jordan Hotel

10/10 Excellent

"We stayed for two nights and had a great time. We stayed in a suite with a kitchenette. It was a very long walk down to the end of the building. I was just recovering from a knee injury so the walk from a far away parking lot and then all the way down the end of the building was not ideal. I did tell the receptionist I just came off crutches so not sure why she put me in the farthest room possible? Next time, I will request a room closer to the pool and gym entrance. There also is very little signage so finding everything was difficult to navigate. The restaurant was closed both times we went downstairs to eat so we had to grab food at the cafe. It was grab and go and very expensive. The pool area and hot tubs were wonderful and the kids enjoyed them. It was relaxing and quiet and much cheaper than renting a VRBO in that area. I prefer a house rental but the prices are out of control."

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."

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 £91 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?

Luxury Lakefront Estate on 138 Acres - Pickleball, Reunions & Weddings: This holiday home rental outside of Greenwood is located on a lake, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a library and 1 hot tub.

How many holiday rentals will I find in Greenwood?

With 20 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?

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 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.

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Check prices for these dates

Our top choices for Greenwood holiday rentals

1. Treehouse With Hot Tub Close to Sunday River!