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Holiday Rentals in Greenwood

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Find properties with these dates

Tonight
May 4 - May 5
Tomorrow
May 5 - May 6
Next weekend
May 10 - May 12

Holiday Rentals in Greenwood

Outdoor pool, a heated pool
9 Bedroom Estate, Sleeps 24, Heated Pool, Hot Tub, Movie Theater, Game Room
10.0 out of 10, Exceptional, (21)
"What a great house for a large group. We highly recommend! Clean, fantastic set up. Well supplied. Fantastic views. Awesome place. We loved it and hope to rebook again."
The price is €1,151
includes taxes & fees
27 May - 28 May
9 Bedroom Estate, Sleeps 24, Heated Pool, Hot Tub, Movie Theater, Game Room
Aerial view
Pet Friendly/Mt. Home/Beau Views/ 3 or more nights 20% DISC!
10.0 out of 10, Exceptional, (26)
"We only had a very brief stay, alas, but made the most of the opportunity as best we could. A few updates are needed with the introductory welcome materials and equipment information that will be easy but useful to correct. Glad we had a chance to pause in western Maine, with a view of close mountains and the distant Presidential Range in NH. A couple of kitchen tweaks will be helpful for our cooking happy selves, though we enjoyed the spacious kitchen with adequate equipment, beautiful place...
The price is €526
includes taxes & fees
6 May - 7 May
Pet Friendly/Mt. Home/Beau Views/ 3 or more nights 20% DISC!
Fridge, microwave, oven, stovetop
Winter Park Lodge- Private Chalet
10.0 out of 10, Exceptional, (16)
"I rented the house for my son and his friends for a birthday weekend. We thoroughly enjoyed the house. It was comfortable and well stocked with everything you would need. I would highly recommend this house!"
Winter Park Lodge- Private Chalet
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Sun-loungers, beach towels
Swim, Kayak, lawn games. Walk to ice cream. Live Theatre , firepit smores!
10.0 out of 10, Exceptional, (79)
"Second time at this rental and more to come - lovely home, awesome host, and a great area!"
Swim, Kayak, lawn games. Walk to ice cream. Live Theatre , firepit smores!
TV, fireplace, DVD player
Cozy Thompson Lake Cabin w/ Boat Dock & Launch
10.0 out of 10, Exceptional, (1)
"We arrived when electric crews were restoring service to everyone, and when the generators stopped, the sounds of loons and ducks took over. The property is adorable, you are literally 2 steps from the water. We couldn't stop watching the ducks, different birds, a heron parade down the cove. It was also the perfect location to watch the solar eclipse, privately, quietly. The beds were so comfortable, the wood stove took the chill out of the main room, the quiet was just right. It was also just...
Cozy Thompson Lake Cabin w/ Boat Dock & Launch
Beach nearby
Cabin between Two Lakes -Private Beach on Moose Pond Minutes to Pleasant Mt Ski
10.0 out of 10, Exceptional, (18)
"Thank you for a great long weekend in Maine. Half of our family enjoyed skiing at Mt. Pleasant for a day when the other half of our family cross country skied at king pine. We were able to snow shoe locally at Pondicherry park in Bridgton too and were able to use your snow shoes that were provided at the house. Thank you! We were a short drive to the movies, outlets, and bowling to break up the outside activities. Each night we cooked at home and had all the dishes/pans we needed. Loved your...
Cabin between Two Lakes -Private Beach on Moose Pond Minutes to Pleasant Mt Ski
Property grounds
5 STAR HOME - Mtn Views, AC, Hot Tub, Firepit, Theater - 10 Mins to Sunday River
10.0 out of 10, Exceptional, (266)
"It’s a beautiful house and so comfortable. We didn’t want to leave but we had so much fun."
5 STAR HOME - Mtn Views, AC, Hot Tub, Firepit, Theater - 10 Mins to Sunday River
2 bedrooms, iron/ironing board, WiFi, bed sheets
5 STAR Magical Waterfront Cabin on Papoose Pond! 25 Minutes to Sunday River.
10.0 out of 10, Exceptional, (46)
"We loved this cozy cabin. It had a rustic feel but was updated enough to be comfortable. Location was great, felt isolated but still close enough to town. Peace and quiet on the frozen lake. The kids loved the little reading nook upstairs. There were plenty of games and toys for them, and they loved tuning in the antique radio. We loved sitting by the gas stove. Bedrooms were spacious and beds were comfortable. There were some minor issues that didn’t significantly detract from our stay (no...
5 STAR Magical Waterfront Cabin on Papoose Pond! 25 Minutes to Sunday River.
Fridge, microwave, oven, stovetop
Cozy Cabin in the White Mountains of Maine
10.0 out of 10, Exceptional, (4)
"Clean, peaceful just beautiful"
Cozy Cabin in the White Mountains of Maine
Snow and ski sports
ECLIPSE SPECIAL!!! INDOOR POOL, HOT TUB, PRIVATE sleeps 18
10.0 out of 10, Exceptional, (27)
"Fantastic property, as advertised and even better than pictures indicated. Would stay again and highly recommend for large group skiing or playing golf in surrounding area."
ECLIPSE SPECIAL!!! INDOOR POOL, HOT TUB, PRIVATE sleeps 18
Terrace/patio
Chalet in Western Maine, Fireplace, Fire pit, sleeps 6
10.0 out of 10, Exceptional, (15)
"Great rental house for 6. Property was clean and well maintained, amnesties were what we needed. Self check-in/out process was too easy. Looking forward to revisiting in the future."
Chalet in Western Maine, Fireplace, Fire pit, sleeps 6
Fridge, microwave, oven, stovetop
River Ridge Lodge with Hot Tub
10.0 out of 10, Exceptional, (12)
"Clean and well equipped"
River Ridge Lodge with Hot Tub
Property grounds
Cedar🏡 Waterfront💦 Hot tub🔥 Pool🎱 Privacy 🕵️
10.0 out of 10, Exceptional, (7)
"Jonathan's property on Sand Pond is well equipped, clean, and comfortable. The location had a wonderful remote feel to it, although it was only a short drive to the adorable town of Norway. We highly recommend a stay at this property"
Cedar🏡 Waterfront💦 Hot tub🔥 Pool🎱 Privacy 🕵️
Fridge, microwave, oven, stovetop
Cozy Cottage w/ Lil' Pond, Fenced Yard & Firepit (Dog friendly!)
10.0 out of 10, Exceptional, (12)
"We enjoyed the cottage as it had everything we needed to prepare meals including pots and pans, spices, a lovely kitchen, towels and linens, shampoo and body wash in the shower. We loved the open concept and close proximity to downtown Bethel. The fenced-in yard was so convenient for the dogs. Hosts Adam and Suz were great, responsive and helpful. We would stay again!"
Cozy Cottage w/ Lil' Pond, Fenced Yard & Firepit (Dog friendly!)
Exterior
Lakefront home with lovely lake views - one mile from the casino
9.8 out of 10, Exceptional, (31)
"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
Fridge, microwave, stovetop, dishwasher
Pet-Friendly Countryside Home: 4 Mi to Long Lake!
9.8 out of 10, Exceptional, (9)
"It family lives out of state and has a dog. This rental was a great place for us to relax and a place for our adult kids too come for a visit. It was really nice. Kitchen was week equipped for a family meal."
Pet-Friendly Countryside Home: 4 Mi to Long Lake!
Property grounds
Fully renovated home with lake view, dock & mooring access, kayaks, & deck
9.6 out of 10, Exceptional, (20)
"We loved this cute little cabin! Just enough space for our family of four. Great kitchen. Very clean. Close to skiing. We would totally stay here again."
Fully renovated home with lake view, dock & mooring access, kayaks, & deck
Fridge, microwave, oven, stovetop
Lakefront, dog-friendly home with dock, kayaks, SUPs, canoe, huge deck & firepit
9.4 out of 10, Exceptional, (14)
"This is the second year we have stayed at this home for our winter holiday. We have enjoyed our visits and found the home to have everything we need. We were pleased to find the fireplace in working order, even though we received a note that it was not working. That and the large kitchen are the natural gathering spots for our family. Watching the ice fishing on the lake is an added bonus. Thank you for sharing this lovely property. We'll be back!"
Lakefront, dog-friendly home with dock, kayaks, SUPs, canoe, huge deck & firepit
Living area
Lovely home on Crystal Lake with private dock, lake views, deck, & grill
9.0 out of 10, Wonderful, (18)
"This is an ideal location for a fun getaway for any season. Plenty of room for a large/extended family. While there is a road between the house and lake it didn’t detract from the experience at all. Pro tip, in cooler seasons turn on the ceiling fans to push the warmer air down. Otherwise the main room will feel cold. The dock is slightly off level and a couple doors don’t latch completely but those are just signs of a well loved camp."
Lovely home on Crystal Lake with private dock, lake views, deck, & grill
Smart TV, fireplace
Lakeside house with a separate bunkhouse
9.0 out of 10, Wonderful, (6)
"We had a great stay on Tripp Lake. House was clean and well cared for and we were surprised and pleased there was AC in the main bedroom. The location was unbeatable — back door was literally steps from the lake and the lake was the star of the trip. We spent the day on the deck, on the dock, or in the water. Host was available and helpful. Would come again!"
Lakeside house with a separate bunkhouse
Don't see what you're looking for?
See all available properties in Greenwood
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.

Other types of properties in Greenwood you may be interested in

Restaurant
Hampton Inn Oxford
2.5 star property
9.0 out of 10, Wonderful, (990)
"Checking was exceptional. Desk staff was very friendly. Room was clean and the beds were comfy. Free hot breakfast was very tasty with a good selection of food. Eating area was very clean. I highly recommend this place!"
The price is €120
includes taxes & fees
12 May - 13 May
Hampton Inn Oxford
Front of property
Oxford Casino Hotel
3.0 star property
8.6 out of 10, Excellent, (754)
"nice and new"
The price is €131
includes taxes & fees
6 May - 7 May
Oxford Casino Hotel
Exterior
Jordan Hotel
3.0 star property
8.4 out of 10, Very good, (212)
"Jordan Hotel offered superior service. Staff were welcoming and accommodating from the first to last. Thank you for your excellent service! Pool and Hot tub were delightful. Sliders restaurant provided delicious and abundant food in pleasing setting. "
The price is €193
includes taxes & fees
5 May - 6 May
Jordan Hotel
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.

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 €526 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?

Lovely home on Crystal Lake with private dock, lake views, deck, & grill: This holiday home rental outside of Greenwood is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden.

How many holiday rentals will I find in Greenwood?

With 24 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 Pennesseewassee lake. In the wider area, you’ll find Mt. Abram and Oxford Plains Speedway.

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.

Recent reviews of Greenwood properties
Expedia verified reviews

Oxford Casino Hotel

Oxford Casino Hotel

5/5 Excellent
"Property was clean; beds comfortable ; noise level less than expected plus, think about it: It’s the only place to stay on the area that’s what would expect in cities or resort areas."
A verified traveller stayed at Oxford Casino Hotel
Posted 6 days ago
Oxford Casino Hotel