Photo by Robbie Martin

Woodstock vacation rentals

We found 413 vacation rentals — enter your dates for availability

Discover a selection of 21 homes and other vacation rentals in Woodstock that are perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll find the best amenities for hanging out with the people that matter most, including parking and a TV. Whatever you're looking for, you'll find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Woodstock

Showing deals for:May 8 - May 15

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Find out more about Woodstock

Why visit Woodstock

  • Outdoor Adventures: Experience thrilling activities like skiing, hiking, and exploring beautiful lakes and waterfalls.
  • Scenic Beauty: Enjoy breathtaking landscapes, with the charm of Woodstock nestled between New Hampshire and New York.
  • Cozy Accommodations: Choose from charming cabins, private vacation homes, or the welcoming Woodstock Inn for a perfect getaway.
  • Friendly Locals: Experience warm hospitality from the welcoming community, enhancing your vacation experience.
  • Memorable Activities: Engage in outdoor fun suitable for families, friends, and couples, ensuring lasting memories.

Popular types of accommodation in Woodstock

If you’re exploring accommodations in Woodstock, you’re in for a treat. The most popular options include Houses, charming Cabins, and cozy Cottages. Whether you’re looking for a rustic cabin rental, a welcoming hostel, or a relaxing stay at Woodstock Inn, we’ve got the perfect spot for you. Enjoy the beauty of Woodstock while finding the ideal home away from home.

  • Houses: The top choice for visitors to Woodstock, these homes offer spacious accommodations ideal for families, friends, or couples looking for comfort and privacy.
  • Cabins: A close second, cabins provide a rustic charm and are perfect for nature enthusiasts seeking a cozy retreat in the woods.
  • Cottages: These quaint and charming residences are the third most popular, offering a warm and inviting atmosphere for a relaxing getaway.
  • Chalets: Known for their unique architecture, chalets provide a picturesque setting for those wanting a blend of comfort and style.
  • Condos: Rounding out the list, condos are a convenient option for travelers looking for modern amenities and easy access to local attractions.**

Top attractions in and around Woodstock

Woodstock, Maine, is a fantastic destination for outdoor enthusiasts, offering a perfect blend of adventure and romance. Visitors can explore beautiful lakes, scenic waterfalls, and exhilarating ski resorts, making it ideal for those seeking breathtaking landscapes and thrilling activities. Whether you're traveling with family, friends, or a partner, Woodstock promises a memorable experience filled with natural beauty and outdoor fun.

  • Sunday River: A premier ski resort located 14 miles from Woodstock, Sunday River is perfect for skiing and outdoor adventures. With its stunning slopes and vibrant atmosphere, it attracts thrill-seekers and families alike, offering a range of winter sports and activities.
  • Shagg Pond: Nestled within Woodstock, Shagg Pond is a picturesque lake known for its serene beach and beautiful scenery. Ideal for romantic getaways or tranquil days outdoors, it's perfect for swimming, picnicking, and enjoying nature.
  • Snow Falls: Located 7 miles from Woodstock, Snow Falls is a breathtaking waterfall that offers adventure and romance. Surrounded by lush landscapes, it's a great spot for hiking, photography, or simply soaking in the beauty of nature.

Things to do recommended for couples

Looking for a romantic getaway in Woodstock, Maine? Enjoy skiing together at Mt. Abram or the adventurous slopes of Sunday River. For a cozy evening, catch a live show at 49 Franklin and immerse yourselves in the local entertainment vibe. Create unforgettable memories together.

Things to do recommended for families

Your family will love exploring the scenic beauty of the nearby White Mountain National Forest, perfect for hiking and picnicking. Don't miss the fun at the local blueberry farms, where you can pick fresh berries and enjoy tasty treats together.

Things to do recommended for groups

In Woodstock, groups can hike the scenic Bethel Pathway, play a round at the Sunday River Golf Club, or enjoy a performance at the Deertrees Theatre and Cultural Center. Each location offers unique outdoor adventures, sports, and cultural experiences for everyone to enjoy.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're traveling with a group, with family, bringing your pets, or planning an extended stay, be sure to prioritize your preferences when filtering your options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Woodstock with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Woodstock with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Woodstock: For many families, a trip isn't truly finished without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Woodstock: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding amenities like a parking space, a well-equipped kitchen, or a private pool to enhance your search experience.

Where to stay in Woodstock

Woodstock, Maine, is a hidden gem perfect for outdoor enthusiasts seeking adventure. Nestled near the stunning landscapes of New Hampshire and the scenic beauty of New York, this charming village offers cozy cottages and opportunities for skiing and exploration. Experience the warm hospitality of friendly locals while enjoying excursions that showcase the area's breathtaking scenery. Whether you're looking for a serene getaway or thrilling outdoor activities, Woodstock promises an unforgettable vacation experience.

  • Bethel: Bethel is a charming city located 9 miles from Woodstock, known for its thrilling outdoor activities and vibrant community. This picturesque town is a haven for adventure seekers, offering easy access to ski fields and resorts where you can hit the slopes during the winter months. In warmer weather, explore the stunning lakes and mountains that surround the area, perfect for hiking, fishing, and enjoying nature. Bethel's quaint downtown features local shops and eateries, adding to its inviting atmosphere, making it a delightful stop for both relaxation and adventure.
  • Bryant Pond: Nestled within the beauty of the Maine wilderness, Bryant Pond is the city where Woodstock resides, offering a unique blend of outdoor activities and serene landscapes. This area is ideal for those looking to immerse themselves in nature, with a strong focus on skiing and outdoor adventures. The nearby lakes and mountains provide ample opportunities for swimming, hiking, and enjoying the beach. Bryant Pond's welcoming environment and recreational facilities make it a perfect destination for families and outdoor enthusiasts alike, ensuring a memorable vacation experience.
  • Newry: Located 11 miles from Woodstock, Newry is a vibrant city that attracts travelers seeking both excitement and tranquility. Known for its excellent skiing options, this area features world-class ski fields and resorts, catering to winter sports enthusiasts of all levels. Beyond skiing, Newry is surrounded by magnificent mountains and serene lakes, offering year-round recreational opportunities such as hiking, mountain biking, and fishing. Visitors can enjoy the breathtaking natural beauty while also indulging in the local culture, making Newry a fantastic addition to your Maine vacation itinerary.

Best time to go to Woodstock

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January15.8°F (-9.0°C)Light RainMostly SunnySlightly HighSlightly High
February17.8°F (-7.9°C)Light RainMostly CloudySlightly LowSlightly High
March26.2°F (-3.2°C)Light RainMostly CloudySlightly HighAverage
April38.1°F (3.4°C)Light RainMostly CloudyAverageAverage
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 SunnySlightly HighAverage
August64.4°F (18.0°C)Light RainMostly SunnyAverageAverage
September57.4°F (14.1°C)Light RainMostly SunnyAverageSlightly Low
October45.9°F (7.7°C)Light RainMostly SunnyAverageSlightly Low
November33.3°F (0.7°C)Light RainMostly SunnySlightly LowAverage
December23.5°F (-4.7°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming travels? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking an extended stay to enjoy even greater savings. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Save more with One Key

When you reserve an eligible Vrbo for your group getaway, you'll earn OneKeyCash on the full booking amount. Being the organizer has its perks. Become a member of our One Key rewards program to unlock exclusive savings and earn OneKeyCash on qualifying stays. Sign up today and start reaping the benefits.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers an easy-to-use platform for organizing your travel plans. You can effortlessly create new trips, continue from where you last left off, or review and arrange your existing itineraries. Your saved or booked properties will be neatly organized into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Welcome to Woodstock - no, not that Woodstock

Any town whose main highlight is a small pond is bound to be charming. That’s the story in Woodstock, a delightful, rural area that shares a name with the famous concert site. This Woodstock, however, is known as the home of the very last crank phone in existence. It’s a dream for anyone who loves and appreciates all things—and we do mean all things—winter. Booking a Woodstock vacation rental is likely to put you in the center of a snow mound, a ski slope, or a snowmobile trail. If you arrive in the summer, you can languish pond-side and soak up the sunshine.

Home of the world's last hand-crank phone

Add this to your quirky attractions file. Those who appreciate the unusual may book a Woodstock vacation rental solely to see the sculpture of the 14-foot candlestick phone located in Remembrance Park. It was designed in honor of the old-school hand-crank phone system, which locals used until 1983. You can also delve into the area’s history thanks to the Woodstock Historical Society, which runs the Woodstock Museum. It’s filled with everything from ancient signs and vintage bicycles to old town photographs and artifacts.

And the sky is a hazy shade of winter

There are definitely 4 distinctive seasons in Woodstock. The predominant 1 is winter, only because snow falls with such ferocity every year. The city’s average snowfall is a whopping 76 inches. That said, you can enjoy your Woodstock vacation rental on a sunny day, too—it shines year round, and summer offers pleasant highs of at least 77 degrees. Those temperatures drop quickly in late September, providing that typical early evening breeze. Springtime is a considerably rainy period, with averages of around 44 inches.

In the north, the black bear beckons

Bryant Pond is the sparkling gem of Woodstock. It feeds into the Little Androscoggin River, but the beauty of this sweet spot is in its quiet tranquility. At the northwest end of town is the aptly named North Pond, where breathtaking views of Moody Mountain can be seen for miles. There are other mountains in Woodstock, too—smaller, humbler hills like Mollyockett, Whitman, and Spruce. Part of the county is home to Umbagog National Wildlife Refuge, about an hour north, where an intriguing mix of marine life and wildlife reside. Keep your eyes open for those black bears.

Transportation to and around Woodstock

The nearest airport is in Auburn, ME (LEW-Auburn - Lewiston Municipal), located 28.8 mi (46.4 km) from the city center. If you can't find a flight that works for your travel itinerary, you might consider flying into Fryeburg, ME (FRY-Eastern Slopes Regional), which is 33.3 mi (53.6 km) away.

Frequently asked questions

What is the best area to stay in Woodstock when booking a vacation rental?
When planning a vacation in Woodstock, Maine, one of the best areas to consider for your stay is the village center. This charming area offers a delightful blend of local culture and convenience, making it an ideal base for your explorations. Here, you'll find a variety of vacation rentals that cater to different needs, from cozy cabins to spacious homes. The village center is known for its picturesque landscapes and warm community vibe, with numerous properties available for booking.

Staying in the village center puts you in close proximity to great attractions such as the stunning Kancamagus Highway, renowned for its breathtaking views and outdoor activities. Additionally, the nearby White Mountain National Forest offers excellent hiking trails and opportunities for nature enthusiasts to immerse themselves in the beauty of the area. Exploring these natural attractions can easily fill your days with adventure.

Another appealing neighborhood is the area around the Bethel region, which is just a short drive from Woodstock. This location features a range of vacation rentals located among scenic surroundings. It provides easy access to local ski resorts, such as Sunday River, making it superb for winter sports enthusiasts.
How much does it cost to rent a vacation home in Woodstock?
Prices for vacation rentals in Woodstock 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Woodstock to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Woodstock vacation house rentals?
You can find great discounts on house rentals in Woodstock on Vrbo, 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 find long-stay vacation rentals in Woodstock?
A long-stay vacation rental in Woodstock is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any Woodstock vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Woodstock with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo 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.
When is the best time to visit Woodstock for a vacation rental?
The best time to visit Woodstock for a vacation rental is during the vibrant summer months of June to August, with July being the most popular time. This peak season attracts travelers eager to embrace the outdoors, as the warm weather creates the superb backdrop for hiking, biking, and enjoying the stunning natural beauty of the area.

During this time, you can expect average temperatures in the high 70s to low 80s Fahrenheit, ideal for exploring the picturesque landscapes and indulging in various outdoor activities. The lush greenery and vibrant wildflowers enhance the charm of Woodstock, making it a delightful destination for both adventure seekers and those looking to unwind in nature.

If you're considering a more budget-friendly option, visiting in December can be a hidden gem. Although it's the low season, December offers a magical winter wonderland experience, complete with snow-covered landscapes superb for cozy holiday getaways. The serene ambiance allows for peaceful hikes and the opportunity to enjoy the local culture without the summer crowds.

Ultimately, your choice of when to visit Woodstock will depend on your preferences for outdoor activities and the atmosphere you wish to experience.
How early should I book a Woodstock vacation rental?
Book your Woodstock vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Woodstock?
In Woodstock, Maine, visitors can discover a variety of attractions that highlight the area's natural beauty and outdoor activities. The town is near the stunning White Mountain National Forest, which offers excellent opportunities for hiking, mountain biking, and scenic drives. The nearby Bethel area features ski resorts like Sunday River, appealing to winter sports enthusiasts.

For those interested in local culture, the quaint downtown area of Woodstock showcases charming shops, local art galleries, and cozy cafes. The historic East Bethel Baptist Church is another point of interest, reflecting the area's rich history.
Can I change or cancel my Woodstock home rental booking on Vrbo?
To find Woodstock vacation rentals with free cancellation, just use Vrbo'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". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Woodstock vacation rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

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