Photo by Robbie Martin

Greenwood vacation rentals

We found 840 vacation rentals — enter your dates for availability

Discover a selection of 21 homes, 11 chalets, and vacation rentals in Greenwood that are perfect for your trip. Whether you’re staying in a vacation home with your kids and pets or just with friends, you'll find the amenities you need and want, including parking and a TV. Whatever you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Greenwood

Showing deals for:Nov 14 - Nov 21
  • 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, yards and more
  • More for less

    More space, more privacy, more amenities — more value

Find out more about Greenwood

Find out more about Greenwood

Why visit Greenwood

  1. Outdoor Adventures: Enjoy a wealth of activities like skiing, hiking, and exploring scenic lakes and majestic mountains.
  2. Picturesque Waterfalls: Discover stunning waterfalls that offer breathtaking views and great photo opportunities.
  3. Charming Accommodations: Stay in cozy cabins, charming cottages, or private vacation homes that enhance your getaway experience.
  4. Welcoming Community: Experience the friendly atmosphere and local charm that make Greenwood a delightful destination.
  5. Shopping at Greenwood Park Mall: Take a break from nature to explore shops and boutiques for a unique shopping experience.

Popular types of accommodation in Greenwood

If you’re planning a getaway to Greenwood, you're in for a treat! Our vacation rentals offer a variety of popular accommodations, including houses, charming cottages, and cozy cabins. Whether you're looking to unwind by the lake or explore the beautiful surroundings, you’ll find the perfect rental that fits your needs. Experience the best of Greenwood with our transparent, savings-focused options for your next adventure!

  • Houses: The top choice for visitors in Greenwood, these spacious rentals offer a homely atmosphere, ideal for families or groups seeking comfort and privacy.
  • Cottages: Quaint and charming, cottages are the second most sought-after option, providing a cozy retreat surrounded by nature.
  • Cabins: A popular third choice, cabins offer rustic charm and the perfect setting for a getaway in the wilderness.
  • Chalets: These stylish mountain lodges are fourth in popularity, perfect for those looking for a blend of luxury and nature.
  • Condos: Rounding out the list, condos provide modern amenities and convenience for travellers wanting easy access to local attractions.**

Top attractions in Greenwood

Greenwood, Maine, is an excellent destination for outdoor enthusiasts seeking skiing, adventure, and scenic beauty. With stunning lakes, picturesque waterfalls, and majestic mountains, this charming town offers a variety of attractions perfect for romantic getaways or immersive nature experiences. Whether you’re exploring the great outdoors solo or with loved ones, Greenwood promises memorable adventures and breathtaking landscapes that showcase the best of Maine's natural charm.

  1. North Pond: Located 8.0km from Greenwood, North Pond offers a romantic lakeside experience with stunning scenery and outdoor activities. Enjoy the beach vibes while swimming, picnicking, or simply soaking in the tranquil atmosphere.
  2. Snow Falls: Situated 9.7km away, Snow Falls is an adventurous waterfall surrounded by natural beauty. The area is perfect for outdoor exploration, hiking, and capturing breathtaking photographs of the cascading water.
  3. Mineral Collector: Just 8.0km from Greenwood, this attraction provides a relaxing environment where you can discover and collect unique minerals, making it a perfect spot for leisurely exploration and learning.

Things to do recommended for couples

For a romantic getaway in Greenwood, indulge in skiing at Mt. Abram for an exhilarating day on the slopes. Venture 22.5km to Little White Cap Ski Lift for more adventure, then enjoy a lively evening at 49 Franklin, just 19.7km away, for an unforgettable music concert.

Things to do recommended for families

Families visiting Greenwood can enjoy a relaxing day at Pondicherry Park, located 30.6km away. This recreational area offers wellness vibes and is perfect for unwinding together while exploring nature and outdoor activities that the whole family can enjoy.

Things to do recommended for groups

Your group can enjoy an exciting getaway in Greenwood, Maine, by visiting the Oxford Casino for a lively evening, racing thrills at Oxford Plains Speedway, or exploring the beautiful Bethel Pathway for a scenic hike surrounded by nature.

What do I need to keep in mind when booking a vacation in Greenwood

If you're travelling with a group, your family, your pets, or planning for an extended stay, be sure to refine your search according to your key priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Greenwood with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Greenwood with young kids: Traveling with young kids can present its challenges. It's important to prioritize their comfort and safety, along with ensuring access to age-appropriate amenities like private swimming pools. Additionally, keeping in mind your closeness to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Greenwood: For many families, a vacation wouldn’t feel complete without their furry companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Greenwood: If you're in search of vacation rentals that offer special deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay in Greenwood

Greenwood, Maine, is a perfect getaway for adventure seekers and families alike. With its breathtaking outdoor scenery and friendly atmosphere, you'll find abundant opportunities for skiing and other outdoor activities. Explore nearby neighborhoods for a taste of the local charm, and don't miss the Greenwood Park Mall for some shopping. This tranquil destination promises a relaxing escape while ensuring you connect with nature and the welcoming community.

  • Bethel: Bethel is a charming city located 14.5km from Greenwood, known for its exceptional outdoor adventures and vibrant community. It attracts visitors seeking thrilling experiences, especially in skiing and sports. The nearby ski fields and resorts offer fantastic winter sports opportunities, while the breathtaking natural surroundings, including serene lakes and majestic mountains, provide ample chances for exploration and relaxation. Bethel's quaint downtown area features delightful shops and eateries, making it a perfect spot to unwind after a day of adventure.
  • Bryant Pond: Just 6.4km away from Greenwood, Bryant Pond is a picturesque city that offers a perfect blend of outdoor activities and scenic beauty. Known for its stunning natural landscapes, visitors flock here for skiing and a variety of adventures. The local ski fields and resorts make it an ideal destination for winter sports enthusiasts. In addition to skiing, Bryant Pond features beautiful lakes and beaches, perfect for summer activities like swimming and picnicking. The tranquil atmosphere and natural beauty make this city a must-visit for those looking to connect with nature.
  • West Paris: Located a mere 6.4km from Greenwood, West Paris is a delightful city known for its stunning scenery and outdoor pursuits. With its proximity to ski resorts and fields, it is a haven for adventure seekers, particularly during the winter months. The area boasts breathtaking views of lakes, mountains, and even a national state park, offering countless opportunities for hiking, camping, and wildlife spotting. West Paris is perfect for those who appreciate the great outdoors and want to experience the serenity of Maine's natural landscapes.

Best time to go to Greenwood

If you're planning a trip to Greenwood, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in September and December to January, while off-peak times, like April and October to November tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January16.2°F (-8.8°C)Light RainMostly CloudySlightly HighSlightly High
February17.8°F (-7.9°C)Light RainMostly CloudyAverageSlightly High
March26.2°F (-3.2°C)Light RainMostly CloudyAverageAverage
April38.1°F (3.4°C)Light RainMostly CloudySlightly LowAverage
May51.6°F (10.9°C)Light RainMostly SunnyAverageSlightly Low
June59.5°F (15.3°C)Light RainMostly SunnyAverageAverage
July66.0°F (18.9°C)Light RainMostly SunnyAverageAverage
August64.4°F (18.0°C)Light RainMostly SunnyAverageAverage
September57.4°F (14.1°C)Light RainMostly SunnySlightly HighSlightly Low
October45.9°F (7.7°C)Light RainMostly SunnySlightly LowSlightly Low
November33.3°F (0.7°C)Light RainMostly SunnySlightly LowAverage
December23.5°F (-4.7°C)Light RainMostly CloudySlightly HighSlightly High

Booking with Vrbo is simple

Are you hoping to save on your upcoming travels? Being flexible with your travel dates can be a great way to take advantage of price variations. Additionally, opting for an extended stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options for your trip!

Vrbo Trips: Planning made easy

Vrbo's innovative Trip Board offers you a dedicated space to plan new adventures, pick up where you left off, or manage your travel arrangements. You can easily find the properties you've saved or booked in the Potential, Upcoming, or Current Trips sections. To start using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Take in the natural beauty of Greenwood

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

Activities and attractions in and around Greenwood

Are you hoping to discover attractions to visit while you're in the area? Venture out of your vacation home and experience everything that makes Greenwood a fun place to get away. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Mt. Abram (5.1 mi / 8.2 km)
  • Sunday River (15.1 mi / 24.3 km)
  • Sunday River Golf Club (16.5 mi / 26.6 km)
  • Black Mountain (17.9 mi / 28.9 km)
  • Mineral Collector (4.8 mi / 7.8 km)
  • Dyna at Vestasen (9.3 mi / 15 km)

Exploring the natural landscape of Greenwood

Whether you're an adventurous traveler or just want to spend some time taking in the scenery, Greenwood is a great spot to appreciate mother nature. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • Papoose Pond (6.7 mi / 10.8 km)
  • Pennesseewassee lake (6.8 mi / 11 km)
  • Kezar Lake (14 mi / 22.6 km)
  • Sunday River (14.2 mi / 22.9 km)
  • Worthley Pond (16 mi / 25.7 km)
  • Highland Lake (16.4 mi / 26.3 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 center. If you can't find a flight that's convenient for your trip, you might consider flying into Fryeburg, ME (FRY-Eastern Slopes Regional), which is 27.1 mi (43.7 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Greenwood?
According to our research, houses are the most desirable type of vacation rental in Greenwood. But as you'd expect, everyone's idea of an awesome trip isn't the same. Vrbo has vacation homes of all sizes, shapes and budgets, and we'll help you discover your ideal fit.
How much does it cost to rent a vacation rental in Greenwood?
Length of stay, season and property type are some of the conditions that can determine the price of a vacation home. Simply add your travel dates to find your ideal match. From comfy cabins to expansive villas, all Vrbo vacation rentals provide incredible value.
How much does it cost to rent a beach house in Greenwood?
When you travel and the size and style of the property will influence how much you'll pay for your beachside escape. Put in your Greenwood travel dates to view your available options on Vrbo. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use the filters to select the features and amenities you want.
Are there pet-friendly vacation rentals in Greenwood?
With 23 properties that allow pets, your happy hound can also come along on your Greenwood getaway. Use our filter tool to browse our pet-friendly vacation rentals and find a stay that's pawfect on Vrbo.
Can I rent a house with a pool in Greenwood?
Grab your swimming gear and inflatable flamingo, because there are seven houses with a private pool in Greenwood. Stay at one of these popular vacation rentals and you'll enjoy pool days every day. Simply enter your dates into Vrbo, then check the "pool" filter to find the ideal place for a splashing good time!
What are popular rental amenities in Greenwood?
Tennis, a firepit and a garden top the list of most popular rental amenities in Greenwood. Whether you're heading away on your own, with a partner or a bunch of friends, Vrbo will help you find a vacation rental that suits your tastes with all the extras you're looking for.
Are there large group vacation rentals in Greenwood?
With 10 vacation rentals that can host 10 guests or more in Greenwood, there's no need to leave anyone off your guest list. From family vacations to events like birthday parties and weddings, Vrbo can help you find a large group rental to match the occasion.
Are there vacation rentals in Greenwood that welcome kids?
With 23 family-friendly vacation rentals to select from in Greenwood, there's never been a better time to introduce the kiddos to the thrills of travel. Just click on our "Properties good for families" filter to look for stays packed with conveniences perfect for families on the move, like living rooms, backyards, entertainment areas and bunk beds.
What are the top attractions for families in Greenwood?
Keeping the kids entertained during your vacation in Greenwood is a breeze with these cool family-friendly attractions:

  • Snow Falls
  • Shagg Pond
  • Pennesseewassee lake

Are there one-bedroom vacation rentals in Greenwood?
Greenwood has three one-bedroom rentals on offer. Often situated in well-regarded areas because of their smaller size, a one-bedroom vacation property is great if you're getting away with your partner or a friend. And with comforts such as air conditioning and more privacy than a standard hotel, you'll be able to relax while discovering this top destination.
Can I find two-bedroom vacation rentals in Greenwood?
Greenwood has three two-bedroom properties for you to pick from. Discover a vacation home with all the comfort and space you need at a fantastic price on Vrbo.
Are there vacation rentals with WiFi in Greenwood?
Greenwood has six vacation rentals with WiFi, so you can stay connected during your vacation. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with the family to checking emails, these Vrbo homes make it a breeze to get online.
How can I find vacation rentals with air conditioning in Greenwood?
Greenwood has eight vacation rentals where you'll be able to relax and recharge in air-conditioned comfort. To locate a stay on Vrbo featuring this perk, enter your dates of travel and use the filters to select the "air conditioning" box.
How old do you have to be to rent a vacation rental in Greenwood?
The minimum required age is usually 16, 18 or 21. It can vary from one property to another on Vrbo, so look at the rules of your preferred Greenwood vacation rental before booking your trip.
How long can I rent a vacation rental in Greenwood for?
The length of time you can book a vacation rental in Greenwood is down to the property. Simply enter your preferred dates to see a list of options offering extended stays. With tons of creature comforts like full kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to find somewhere perfect to call your home away from home in Greenwood.

More Vacation Rentals ideas

People also search for