Holiday rentals in Woodstock

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Quick stats about holiday rentals in Woodstock

  • Total holiday rentals

    Explore 100 holiday rentals in Woodstock

  • Nightly prices starting at

    Woodstock holiday rentals start at £75 per night before taxes and fees

  • Verified guest reviews

    Over 4,910 verified reviews to help you choose

  • Family-friendly holiday rentals

    90 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    90 of Woodstock holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Woodstock rentals

  • 4.9 Average rating

    Woodstock stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated holiday rentals in Woodstock

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A private hot tub is situated outdoors, surrounded by greenery and offering views of the lake and mountains in the background. Two glasses of sparkling wine are placed on the tub's edge, reflecting the natural scenery under a clear blue sky.
Home in Woodstock
4.99 out of 5 average rating, 150 reviews

Sunset & Lake View, Theater, HTub, Xbox, Mini Golf

Welcome to the Sunday River retreat in our luxury chalet with the best views in Maine. Our sanctuary can comfortably sleep 12 and boasts Lake Christopher panoramic views with Mt. Abram sights. Minutes from Sunday River Resort, a public boat launch and other area attractions. Private hot tub, fire pit, wood stove and deck await your arrival. Enjoy arcade games, Xbox, a movie theatre room, BBQ grill and speakeasy theme bar setup. Don't forget to take a picture in the gondola and to catch a sunset!

Top guest favourite
Cabin in Chesterville
5 out of 5 average rating, 200 reviews

Off-Grid Cabin with Wood Fired Hot Tub. 4 Kayaks

Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- beautiful swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

Top guest favourite
Cabin in Norway
5 out of 5 average rating, 95 reviews

Secluded Cabin: View, Hot Tub, 10 min Walk to Lake

Architect-designed alpine cabin with panoramic White Mountain views, including Mount Washington Relax in the hot tub, watch the sunset over the mountains, and enjoy a peaceful forest setting close to lakes, hiking trails, and skiing. 4WD or AWD REQUIRED Nov 1st-April 15th Starting May–Fall 2026, there may occasionally be (weekday only) construction noise up the road (250ft) from neighbors building their home. Work would occur roughly 8am–4/5pm and not every day. Cannot see it from the house.

Top guest favourite
A private hot tub is surrounded by trees displaying vibrant autumn leaves, with a gentle stream flowing nearby. A fire pit sits beside the hot tub, offering a cozy gathering space. The cabin's exterior features wooden siding and large windows that invite natural light.
Tiny home in Norway
4.94 out of 5 average rating, 257 reviews

Glass Wall Waterfront Hot Tub Fireplace Tiny Home

Wake up to rushing waterfalls right outside your glass wall in this romantic waterfront tiny home in Norway, Maine! Private hot tub with river views, see-through gas fireplace, cozy raised queen bed overlooking the water, outdoor shower, hammocks, and direct access to hiking trails. Total privacy—no neighbors in sight. Modern kitchen, heated floors, fast WiFi, and thoughtful touches for couples or solo escapes. Romantic getaway near Sunday River skiing, golf & Maine adventures. Nature's oasis

Top guest favourite
Yurt in Woodstock
5 out of 5 average rating, 278 reviews

Luxury Romantic Yurt •Hot Tub •Mt Views •AC •WiFi

Escape to Birdsong Yurt, a romantic and luxurious retreat nestled in the mountains of Maine. Enjoy beautiful mountain views, serene privacy on 2 acres, and a cozy yurt experience you won’t forget. Perfect for couples, friends, or small families seeking a magical getaway. Whether sipping wine under the stars, relaxing sunsets in the hot tub, or cozying up by the fireplace, Birdsong Yurt is your perfect mountain escape. Book your unforgettable experience today! •Full Kitchen/Bathroom •WiFi/AC

Top guest favourite
A cozy cabin is nestled among snow-covered trees, showcasing a wooden exterior in warm tones. The entrance features a welcoming pathway lined with snow, while the nearby deck offers a glimpse into the winter landscape, creating a serene atmosphere in the snowy environment.
Cabin in Hanover
4.99 out of 5 average rating, 533 reviews

Cabin retreat just steps from adventure

Nestled on 80 acres in the woods alongside a stream, this cabin is the perfect retreat. Whether you are looking for a romantic getaway, a family vacation, or a gathering of your closest friends-this cabin is ideal. It is located on a private road and close to Howard Pond, Androscoggin River, and Sunday River skiing. No matter the season, opportunities await, whether you decide to stay close or venture out. There are plenty of trails nearby to explore, canoe rentals, skiing and so much more.

Guest favourite
The chalet-style cabin is surrounded by lush greenery and features a wooden exterior with large windows. A quaint balcony adorns the front, allowing for natural light to fill the space. A gravel pathway leads to the inviting red front door.
Cabin in Woodstock
4.97 out of 5 average rating, 175 reviews

Sunday River & Lake Chalet, 2 Kitchens, Hot Tub

Family-friendly Chalet-Style cabin on three acres. Minutes away from world class skiing and across the street from Glover's Marsh Wildlife Sanctuary and beautiful North Pond, with lake access minutes away. Kayaks available for rent during summer months! Updated recently with upgrades including luxurious Egyptian cotton sheets, memory foam mattress toppers, & plush down alternative comforters. Hot Tub with Pavilion next to new stone firepit! Come relax and enjoy the beautiful Maine landscape!

Top guest favourite
A wooden dock extends into a calm lake, flanked by lush greenery and colorful foliage. Two Adirondack chairs are positioned invitingly at the end of the dock, with a brightly colored blanket draped over one. Reflections of clouds and trees are visible on the water's surface.
Cabin in Woodstock
4.96 out of 5 average rating, 169 reviews

Private Lakefront Cabin in Woods near Sunday River

Private waterfront Cabin in woods, nestled off private dirt road near Mt. Abrams and Sunday River. Kayak, swim & fish in pristine lake in Summer. Skate, XC Ski, Ice Fish, Snowshoe, Hike in Winter. Fireplace and Fire Pit. Excellent wifi - Private, quiet remote workspace. Rustic modern cozy decor: fully-equipped stainless steel kitchen with dishes, utensils, pots, pans, coffee maker & espresso machine. Organic linens. Pristine bathroom-large hot shower area, heat lamp, soaking tub.

Guest favourite
Chalet in Bryant Pond
4.93 out of 5 average rating, 185 reviews

Sunday River | Mt Views | Dog Fndly | 20% Off 3+

Luxury mountain retreat minutes from Sunday River slopes. Designed for discerning guests, this upscale estate features breathtaking panoramic views, a private hot tub, a gourmet chef’s kitchen, and an open living space with a cozy fireplace. Whether you're here for world-class skiing, hiking, or a premium alpine getaway, enjoy high-end finishes and ultimate comfort. Perfect year-round Maine escape for families and groups seeking outdoor adventure and relaxation. Book your stay!

Top guest favourite
Treehouse in Woodstock
4.98 out of 5 average rating, 315 reviews

LuxuryTreehouse w/ Hot Tub Near Sunday River

Escape to an authentic luxury treehouse designed by B’Fer Roth of DIY Network’s Treehouse Guys and built by The Treehouse Guys. Hidden on a private wooded road with no neighbors in sight, this unique retreat borders 626 acres of Bucks Ledge Community Forest with 7 miles of trails right outside your door. Enjoy peaceful seclusion just 15 minutes to Sunday River, 5 minutes to Mt. Abram, and 10 minutes to Bethel for the perfect mix of adventure and relaxation.

Guest favourite
Home in Greenwood
4.96 out of 5 average rating, 131 reviews

Lakefront summer getaway for 6

Restored lakefront home on Main Street with a private dock, canoes, and kayaks steps from your door. Summer means paddling, swimming, and evenings on the lake. Winter means ice skating in the front yard and skiing at Mt. Abrams (5 min) or Sunday River (20 min). Custom kitchen, cozy modern finishes, smart TV, and fast WiFi. One of Bethel/Greenwood's most charming addresses — book before it's gone. Summer will sell out. We newly allow pets!

Top guest favourite
Chalet in Woodstock
4.94 out of 5 average rating, 52 reviews

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

Escape to this spacious 3BR/3.5BA Woodstock retreat, where resort-style amenities meet the comforts of home. Designed to sleep up to 11, the home blends comfort with luxury amenities. You'll find great restaurants, breweries, and outdoor adventures down the road in Bethel. Just minutes from Bryant Pond, Mt. Abram and Sunday River for endless outdoor activities. Make this your perfect getaway for creating lasting memories in every season.

Popular amenities for Woodstock holiday rentals

When is the best time to visit Woodstock?

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Frequently Asked Questions

  • What are the best places to stay in Woodstock?

    Stays in Woodstock are often centered around cozy cabins, lakeside homes, and rentals with mountain views. Properties near Bryant Pond and rural areas are frequently suggested for a peaceful retreat.

  • What are the best things to do in Woodstock with kids?

    Families enjoy lakeside activities at Bryant Pond, hiking local trails, and visiting small community parks. Seasonal nature programs and outdoor adventures are often recommended for kids.

  • What are some of the best things to do in Woodstock?

    Explore scenic lakes like Bryant Pond, hike trails around Mount Pisgah, and join local community events. Boating, fishing, and experiencing the area’s outdoor beauty are frequently suggested.

  • How is the weather in Woodstock?

    Winters in Woodstock are cold, with temperatures around 2–32°F (-16–0°C), while summers bring highs near 75–80°F (24–27°C) and moderate rainfall. Prepare for variable conditions, as spring and fall can be cool and rainy.

  • When is the best time to visit Woodstock?

    Late spring through early autumn is often recommended for milder weather and outdoor festivals. Autumn brings vibrant foliage, while winter has opportunities for snow activities in rural areas.

  • What are the best places to visit in Woodstock?

    Bryant Pond is often recommended for its lakeside charm, while Mount Pisgah draws visitors for scenic hikes. The village center has local shops and gathering spaces rooted in Woodstock’s culture.

  • What are some hiking trails in Woodstock?

    Mount Pisgah is a frequently suggested hike with scenic views, and local trails wind around Bryant Pond and forested areas. Many paths are suitable for families looking for gentle walks.

  • What are some family activities we can do in Woodstock?

    Families can explore lakeside beaches, paddle or kayak near Bryant Pond, and join nature-themed programs. Community parks and hiking trails are also popular for group outings.

  • What are some of the best day trip ideas from Woodstock?

    Day trips often include exploring nearby mountain trails, visiting local farms, or enjoying lakes in the surrounding region. Guests frequently suggest venturing to small towns for crafts, seasonal markets, and nature experiences.

  • Are there any pet friendly accommodations available in Woodstock?

    Woodstock has a range of vacation rentals that welcome pets, especially cabins and homes near forested areas. Many listings specify pet-friendly amenities, so travelers can enjoy outdoor adventures with their companions.

  • What are some local tips for visiting Woodstock?

    Locals recommend connecting with community events, exploring outdoor spaces early in the day, and trying regional produce from markets. Bringing bug spray and layered clothing is suggested for both summer and fall.

  • What is Woodstock known for?

    Woodstock is known for its scenic lakes, outdoor recreation, and vibrant seasonal community events. The area has a history of rural traditions and locally rooted culture.

  • What are the best hidden gems to explore in Woodstock?

    Woodstock has quiet forest trails, small nature preserves, and locally owned shops around the village. Some travelers enjoy peaceful spots by lesser-known ponds and community gardens.

  • What are the best foods to try in Woodstock?

    Woodstock’s dining features locally rooted flavors such as Maine blueberries, maple syrup, and traditional country breakfasts. Small restaurants often highlight homemade baked goods and regional produce.

  • What should I bring for a trip to Woodstock?

    Pack for changing weather with layers, waterproof outerwear, and sturdy shoes for hiking. In warmer months, bring swimwear, sun protection, and insect repellent for lakeside and outdoor activities.

  • What is the nightlife in Woodstock like?

    Woodstock has a quiet, laid-back nightlife with local taverns and community gathering spots. Guests often find live music events and casual venues around the village center, especially on weekends.

  • What are the most popular events or festivals in Woodstock?

    Seasonal festivals are frequently suggested, including autumn harvest celebrations and summer fairs around Bryant Pond. Local events often feature crafts, music, and community gatherings, especially in late summer and early fall.

  • Are there family friendly vacation rentals in Woodstock?

    Many vacation rentals in Woodstock are oriented toward families, offering amenities like outdoor spaces, lakeside access, and board games. Rural homes and cabins are often recommended for group stays.

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  2. United States
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  4. Oxford County
  5. Woodstock