Greenwood holiday rentals

We found 858 holiday rentals — enter your dates for availability
Discover a selection of 20 homes, 12 chalets and holiday rentals in Greenwood that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the amenities that you need and want, which might include parking and a hot tub. At the end of the day, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Greenwood

Showing deals for:8 Jan - 15 Jan

Exterior
Private kitchen
Outdoor dining
Living area
Exceptional
(54 reviews)

Comfortable four season Chalet minutes to all amenities

Bethel

8% off
AU$3,812
for 7 nights, 1 chalet
AU$545 per night
includes taxes & fees
Comfortable four season Chalet minutes to all amenities
Room
Property grounds
Exterior
Interior
Exceptional
(17 reviews)

Fall Foliage in the Treetops! Awesome 5-Star Luxury Treehouse in the Mountains

Rumford

25% off
AU$4,425
for 7 nights, 1 cabin
AU$632 per night
includes taxes & fees
Fall Foliage in the Treetops! Awesome 5-Star Luxury Treehouse in the Mountains
Interior
Room
Interior
Exterior
Exceptional
(10 reviews)

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

Waterford

8% off
AU$6,497
for 7 nights, 1 cottage
AU$928 per night
includes taxes & fees
Ultra Private, Crooked Reflections, Riverside Retreat, Hot Tub, Waterfront Glass
Exterior detail
Outdoor spa tub
Living area
Interior
Exceptional
(26 reviews)

Cedar🏡 Waterfront💦 Hot tub🔥 Pool🎱 Privacy 🕵️

Norway

7% off
AU$5,498
for 7 nights, 1 chalet
AU$785 per night
includes taxes & fees
Cedar🏡 Waterfront💦 Hot tub🔥 Pool🎱 Privacy 🕵️
Queen Bed
Log Cabin
The Hidden Gem Cabin in December
Dining room view from the Living Room
Exceptional
(50 reviews)

Clean Secluded Cabin w/ Incredible Mountain Views!

Mexico

8% off
AU$2,672
for 7 nights, 1 cabin
AU$382 per night
includes taxes & fees
Clean Secluded Cabin w/ Incredible Mountain Views!
Open living space with vaulted ceilings, leather sofa, arm chairs, big screen TV
View from the kitchen, overlooking the dining area & living room, lots of space
Eat in kitchen, all new appliances, and everything you'll need to prepare a meal
Main floor King bedroom, with private bathroom, big screen TV, & closet storage
Exceptional
(16 reviews)

Epic mountain views, Hot tub and Game room

Bethel

8% off
AU$11,256
for 7 nights, 1 cabin
AU$1,608 per night
includes taxes & fees
Epic mountain views, Hot tub and Game room
Private kitchen
Exterior
Interior
Property grounds
Exceptional
(6 reviews)

Treetops at Kezar Lake

Lovell

8% off
AU$5,985
for 7 nights, 1 home
AU$855 per night
includes taxes & fees
Treetops at Kezar Lake
Room
Terrace/patio
Private kitchen
Living area
Exceptional
(53 reviews)

Kezar Lake 4-Bedroom 4-Season House w/Easy Access to Pleasant Mtn/Sunday River

Lovell

8% off
AU$3,354
for 7 nights, 1 home
AU$479 per night
includes taxes & fees
Kezar Lake 4-Bedroom 4-Season House w/Easy Access to Pleasant Mtn/Sunday River
Living area
Terrace/patio
Room
Living area
Exceptional
(6 reviews)

Sunday River House~HTub~Firepit~Wood Stove~Gondola~Move Rm~Amazing Views~Dogs Ok

Bryant Pond

8% off
AU$8,266
for 7 nights, 1 home
AU$1,181 per night
includes taxes & fees
Sunday River House~HTub~Firepit~Wood Stove~Gondola~Move Rm~Amazing Views~Dogs Ok
Exterior
Living area
Kitchen
Exterior
Exceptional
(33 reviews)

Authentic Log Home -Hot Tub, King Bed, and Wood stove-18 Minutes to Sunday River

Greenwood

16% off
AU$4,397
for 7 nights, 1 chalet
AU$628 per night
includes taxes & fees
Authentic Log Home -Hot Tub, King Bed, and Wood stove-18 Minutes to Sunday River
Pick up local goodies, a bottle of wine, and you are ready to eat in!
Enjoy the morning sun as you sip your coffee and enjoy the view
A spacious island for cooking, eating & gathering
Our spacious great room
Exceptional
(13 reviews)

Heated SwimSpa, Sauna, Games, Mtn Views + 7mi to Sunday Rvr, Sleeps 14, Dogs OK

Bethel

8% off
AU$12,124
for 7 nights, 1 home
AU$1,732 per night
includes taxes & fees
Heated SwimSpa, Sauna, Games, Mtn Views + 7mi to Sunday Rvr, Sleeps 14, Dogs OK
Living area
Backyard
Outdoor spa tub
Back of condo
Wonderful
(82 reviews)

Cozy Retreat, Hot tub, Wireless,Close to Kezar Lake, abuts White Mountains

Stoneham

10% off
AU$1,861
for 7 nights, 1 apartment
AU$266 per night
includes taxes & fees
Cozy Retreat, Hot tub, Wireless,Close to Kezar Lake, abuts White Mountains
Front
Private rear yard
Front from road with ample parking
Dining area into kitchen
Exceptional
(44 reviews)

Beautiful Bethel Home, Sunday River, Sleeps 12

Bethel

16% off
AU$5,044
for 7 nights, 1 home
AU$721 per night
includes taxes & fees
Beautiful Bethel Home, Sunday River, Sleeps 12
Outdoor dining
The living room is the heart of the home with its cozy sofas and open layout
The private, three level cabin offers everything you need to enjoy your stay!
The kitchen comes fully equipped with everything you need to make homemade meals
Exceptional
(16 reviews)

Family-friendly, Luxury Log Cabin Nestled in the Woods - 10 Mins to Sunday River

Bethel

11% off
AU$3,584
for 7 nights, 1 cabin
AU$512 per night
includes taxes & fees
Family-friendly, Luxury Log Cabin Nestled in the Woods - 10 Mins to Sunday River
Exterior
Terrace/patio
Room
Interior
Exceptional
(5 reviews)

Perfect Maine Getaway - Waterfront w Sauna and Kayaks

Waterford

8% off
AU$5,540
for 7 nights, 1 home
AU$791 per night
includes taxes & fees
Perfect Maine Getaway - Waterfront w Sauna and Kayaks
Room
House is very private and just steps from water's edge.
Enjoy s'mores at night at the fire pit (Not available in winter).
Log Home overlooking frozen pond.
Exceptional
(150 reviews)

Waterfront Log Home on Quiet Lake - 25 Minutes -Sunday River Ski

Waterford

8% off
AU$3,143
for 7 nights, 1 home
AU$449 per night
includes taxes & fees
Waterfront Log Home on Quiet Lake - 25 Minutes -Sunday River Ski
Room
Exterior
Interior
Private kitchen
Exceptional
(25 reviews)

Skiing, snowshoeing, snowmobile/ATV trails, hunting, hiking and kayaking

Rumford

8% off
AU$4,136
for 7 nights, 1 home
AU$591 per night
includes taxes & fees
Skiing, snowshoeing, snowmobile/ATV trails, hunting, hiking and kayaking
Terrace/patio
Living area
Dining/ Kitchen
Living Room
Exceptional
(10 reviews)

Brand New Mountain House Sunday River

Newry

8% off
AU$16,614
for 7 nights, 1 home
AU$2,373 per night
includes taxes & fees
Brand New Mountain House Sunday River
An open-concept main floor allows all guests to interact with plenty of space
Soak in the hot tub after a day of skiing, hiking, and shopping
Your private cabin is on two acres, yet convenient and close to all your needs
You open-concept living room has comfy leather furniture and a SMART TV
Exceptional
(23 reviews)

Mountain View Chalet with Hot Tub and Game Room

Newry

8% off
AU$9,314
for 7 nights, 1 cabin
AU$1,331 per night
includes taxes & fees
Mountain View Chalet with Hot Tub and Game Room
Interior
Living room.
Master bedroom with an attached half bath, and a washer/dryer.
Fully stocked kitchen with all you need for your stay.
Exceptional
(23 reviews)

Sunnyside home near Sunday River, Black Mountain, Lakes, Rivers and Hikes

Rumford

11% off
AU$2,339
for 7 nights, 1 home
AU$334 per night
includes taxes & fees
Sunnyside home near Sunday River, Black Mountain, Lakes, Rivers and Hikes
Room
Reading corner
Living room
Mudroom/Entryway
Exceptional
(29 reviews)

Eight minutes to Sunday River! Two bdrm apartment. Ski, golf, hike & relax.

Newry

20% off
AU$2,022
for 7 nights, 1 apartment
AU$289 per night
includes taxes & fees
Eight minutes to Sunday River! Two bdrm apartment. Ski, golf, hike & relax.
Dining
Living area
Room
Living area
Exceptional
(7 reviews)

Songo Loft - Old Farmhouse

Bethel

8% off
AU$2,450
for 7 nights, 1 home
AU$350 per night
includes taxes & fees
Songo Loft - Old Farmhouse

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Take in the natural beauty of Greenwood

Learn about the unique charm of Greenwood with a stay in a holiday home rental. One of the city's many top draws is its skiing. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Greenwood

Are you hoping to find attractions to visit in the city? Venture out of your cosy holiday rental and experience everything that makes Greenwood a fun place to get away to. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Mt. Abram (5.1 mi / 8.2 km)
  • Sunday River (15.1 mi / 24.3 km)
  • Black Mountain (17.9 mi / 28.9 km)
  • Sunday River Golf Club (16.5 mi / 26.6 km)

Exploring the natural landscape of Greenwood

Whether you're an adventurous traveller or just want to appreciate the scenery, Greenwood is a great place to get out in nature. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Snow Falls (5.7 mi / 9.1 km)
  • Pennesseewassee lake (6.8 mi / 11 km)
  • Bethel Hill Common (9.1 mi / 14.6 km)
  • Kezar Lake (14 mi / 22.6 km)
  • Sunday River (14.2 mi / 22.9 km)
  • Worthley Pond (16 mi / 25.7 km)

How to get to and around Greenwood

Fly into Auburn, ME (LEW-Auburn - Lewiston Municipal), the closest airport, located 25.9 mi (41.7 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Fryeburg, ME (FRY-Eastern Slopes Regional), which is 27.1 mi (43.7 km) away.

Frequently asked questions

What is the best area to stay in Greenwood when booking a holiday rental?
When considering a holiday rental in Greenwood, Maine, the area surrounding Lake Christopher is one of the best choices. This charming neighbourhood offers a serene lakeside atmosphere, superb for those looking to unwind and enjoy nature. With a variety of properties available, visitors can find options that suit different preferences, whether you're seeking a cosy cabin or a spacious family home.One of the top attractions in this area is the stunning lake itself, where you can indulge in activities such as swimming, kayaking, and fishing during the warmer months. The picturesque scenery makes it an excellent spot for photography and leisurely walks. Additionally, the nearby Mount Abram offers fantastic opportunities for skiing and snowboarding in winter, making Greenwood a year-round destination for outdoor enthusiasts.Another appealing aspect of staying near Lake Christopher is the sense of community it provides, allowing guests to experience the local culture and hospitality.
Where are the best Greenwood ski resort rentals?
For the best ski resort rentals near Greenwood, Maine, travellers should consider the area surrounding the Sunday River Ski Resort, which is just a short drive from Greenwood. The nearby town of Bethel offers a variety of rental options, including cosy chalets and spacious cabins that are great for families or groups seeking a winter getaway. Many of these properties come equipped with amenities such as fully stocked kitchens, wood-burning stoves, and hot tubs, providing comfort and relaxation after a day on the slopes.In Bethel, visitors can also find lodgings featuring convenient access to local shops and dining options, making it easy to stock up on supplies or enjoy a meal out. Some rentals are situated with stunning mountain views, enhancing the overall experience of a ski holiday. The nearby White Mountain National Forest offers excellent opportunities for snowshoeing and cross-country skiing, adding to the winter activities available in the region.
What is the most popular type of holiday rental accomodation in Greenwood?
In Greenwood, holiday houses are the most popular type of holiday rental, with around 40 available throughout the area. These spacious properties often feature multiple bedrooms, fully equipped kitchens, and outdoor spaces ideal for relaxing after a day of exploring the nearby lakes and mountains. Additionally, there are about 22 chalets and 10 cabins, which provide a charming, rustic experience amidst the stunning natural surroundings. Several cottages and condos are also available, offering a variety of options for different group sizes.
Are there any family house rentals in Greenwood?
In Greenwood, Maine, there is a variety of family house rentals available, with around 31 options to choose from. This charming area is superb for families looking to enjoy outdoor activities, as it is close to popular attractions such as the stunning Rangeley Lake and the picturesque Bethel village.Many of these homes come equipped with spacious living areas, full kitchens ideal for preparing family meals, and outdoor spaces superb for children to play safely. Visitors can also expect amenities like Wi-Fi and laundry facilities, ensuring a comfortable stay for everyone.
Are there pet-friendly house rentals in Greenwood?
In Greenwood, there are several pet-friendly house rentals available, providing a great opportunity for travellers looking to enjoy the area's natural beauty with their furry companions. Many of these holiday homes come with amenities such as spacious backyards, fully equipped kitchens, and comfortable living spaces, ideal for families and groups.The area is close to the scenic Lake Christopher, where outdoor activities like hiking, fishing, and swimming can be enjoyed. Additionally, the nearby Oxford Hills region offers beautiful landscapes and charming local attractions.
Are there any remote work holiday rentals in Greenwood?
In Greenwood, Maine, there are numerous options for remote work holiday rentals, with around 78 properties available. This charming area, known for its beautiful landscapes and proximity to lakes, offers a variety of accommodations well-suited for those working remotely. Many of these rentals come equipped with essential amenities such as high-speed internet, Wi-Fi, and comfortable workspaces, ensuring that guests can stay productive while enjoying their holiday.Travellers can expect to find homes featuring spacious living areas, fully equipped kitchens, and serene outdoor spaces, great for taking breaks and enjoying the natural surroundings. The nearby lakes, like the popular Lake Christopher, provide opportunities for relaxation and outdoor activities during downtime, while the local community offers a variety of shops and dining options to explore. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Greenwood?
In Greenwood, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals. Many properties also feature onsite parking, making it convenient for those travelling by car. A coffee or tea maker is often provided for a warm beverage to start the day. Rentals frequently come with a deck or patio, offering outdoor space to relax and enjoy the surroundings. Additionally, many accommodations include a fireplace, creating a cosy atmosphere, especially during the cooler months.
When is the best time to visit Greenwood for a holiday rental?
The best time to visit Greenwood for a holiday rental is during the peak season from December to February. This winter wonderland attracts visitors seeking the thrill of snow sports, with nearby ski resorts offering excellent conditions for skiing and snowboarding. The magical atmosphere of Greenwood during these months is enhanced by the scenic beauty of snow-covered landscapes, superb for outdoor activities like snowshoeing and ice fishing.In December, temperatures typically range from -6 to 3 degrees Celsius, providing a crisp and invigorating climate for those who enjoy winter activities. This month is particularly special with festive decorations and holiday events that create a warm, inviting community spirit. Visitors can revel in the joy of winter festivities while also taking in the stunning winter scenery.For those looking for a more budget-friendly option, consider a visit in April. This month offers a quieter experience as the ski season winds down, allowing for peaceful hikes and the chance to witness the early signs of spring. The transition from winter to spring brings a beautiful transformation to the landscape, making it a lovely time for exploration without the crowds.Ultimately, your choice of when to visit Greenwood will depend on whether you seek the vibrant winter activities of the peak season or the serene beauty of the shoulder months.
What are the top attractions in Greenwood?
In Greenwood, Maine, visitors can enjoy a range of attractions that highlight the area's natural beauty and outdoor activities. The stunning Lake Pennesseewassee is a central feature, great for swimming, fishing, and kayaking during the warmer months. The surrounding area offers numerous hiking trails, with the nearby Mount Abram providing opportunities for both summer and winter sports, including skiing and snowboarding in the colder months.For those interested in local culture, the quaint Greenwood Village features charming shops and eateries that reflect the community's character. Additionally, nearby Bethel is home to the Bethel Historical Society, where visitors can learn about the region's rich history.
Are all fees included in the Greenwood holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Greenwood holiday homes with parking?
Stayz offers a wide selection of holiday homes in Greenwood with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Greenwood holiday homes?
You can find great discounts on holiday homes in Greenwood on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Greenwood holiday home booking on Stayz?
To find Greenwood holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Greenwood?
A long-stay holiday home in Greenwood is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Greenwood holiday home?
Book your Greenwood holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Greenwood?
Prices for holiday homes in Greenwood vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Greenwood to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.