Places to stay near Owl's Head

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Top-rated vacation rentals near Owl's Head

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Guest favorite

A spacious deck is shown overlooking the lake, featuring two lounge chairs and a shaded seating area beneath a parasol. Vibrant autumn leaves surround the scene, reflecting the season's colors against the calm waters of the lake.

Cottage in Newport

4.87 out of 5 average rating, 154 reviews

Lakefront Cabin | Boat Dock-Fireplace-Sunset Views

Nestled in the Rolling Hills of rural Vermont, our Pet Friendly 3BR/2.5BA Lake House has Tasteful Furnishings, Modern Conveniences, and an airy, open design. Enjoy your stay swimming, boating, or fishing on the lake in the summer or exploring the rich history of downtown Newport (15 min drive) and skiing at nearby Jay Peak (30 min drive) in the winter. You will be welcomed with Luxury White Bedding, a Fully Equipped Kitchen, a Beautiful Private Lake Front Dock, and all the Comforts of Home :-)

Top guest favorite

A bright bedroom features a spacious white bed with decorative pillows, accompanied by a small bedside table. A simple desk and chair are positioned in the corner, providing a workspace. Natural light filters in through a nearby window, illuminating the wood flooring and light area rug.

Home in Sherbrooke

5 out of 5 average rating, 32 reviews

Small Town Oasis

Reconnect with loved ones in this pet-friendly, family retreat. This spacious property features 3 bedrooms, workspace and finished basement. A large backyard opens up to a wooded area, perfect for both children and dogs. Close proximity to 2 Universities, our location offers the convenience of city amenities while maintaining the small-town charm you desire. A short drive to numerous lakes, golf courses, ski hills, hiking trails, ensuring your family has plenty of options for a memorable stay.

Guest favorite

A vibrant landscape captures the essence of autumn with colorful trees showcasing shades of red, orange, and yellow. The manicured lawn stretches towards distant mountains under a clear blue sky, inviting outdoor activities and relaxation.

Chalet in Montgomery

4.95 out of 5 average rating, 113 reviews

Montgomery Meadows Chalet near Jay Peak

Located on beautiful, historic Hazens Notch Road, Montgomery Center, Vermont. This “hidden gem” of a house sets back from the road in a private setting on 5 spectacular acres of cleared land, with views of Jay Peak Ski and Golf Resort. A perfect location for skiing, hiking, biking, golfing, etc. Only 15 minutes from the resort and all of the great amenities (water park, ice rink, movie theater, climbing wall, arcade). Only 3 miles from local amenities (grocery store, top rated restaurants).

Guest favorite

A lakefront deck is captured, featuring several striped chairs arranged for seating. Alongside, a round table is visible. Lush greenery surrounds the space, providing shade, while canoes are seen in the background, positioned nearby on the water.

Cottage in Newport

4.76 out of 5 average rating, 51 reviews

Delightful cottage steps from Lake Memphremagog

Cheerful cottage with access to Lake Memphremagog past main house. Large deck on lakefront shared with owner, as well as canoe and double kayak. Clean, sandy-bottomed lake is great for kids and shallow many feet from shore. Nature walks out front door, plus access to bicycle and mountain bike trails. Great fishing with easy motor boat input nearby. Half hour from Jay Peak's summer activities. Reliable WiFi. Cottage has loft with king bed. Living area has futon which converts to double bed.

Guest favorite

An outdoor patio area features two wooden lounge chairs facing a central table, surrounded by greenery. A cozy seating arrangement includes a modern sectional sofa and a distinctive round lounge chair. A barbecue grill is positioned nearby, with stone paving underfoot.

Cabin in Montgomery

4.94 out of 5 average rating, 112 reviews

Mountain Retreat On The Creek

The Jay Peak Retreat - Experience the Northeast Kingdom’s premier destination at Jay Resort, known for its record breaking snowfall and Vermont’s largest indoor waterpark. Upon arrival, welcomed by an open-concept layout perfect for intimate gatherings and après-ski relaxation. The cabin blends high-end resort luxury with tranquility and privacy. Inquire about our Speak Easy Cabin, 15 minutes away. Conveniently located 1 hour from Burlington, 2 hours from Montreal, and 3.5 hours from Boston.

Superhost

Condo in Magog

4.83 out of 5 average rating, 211 reviews

Magog Lovely Vacation Home

This is your lovely vacation home in the beautiful Eastern Townships area. It's a cozy condo with 1 bedroom of a queen bed and 1 floor mattress in the living room. Perfect for couples, solo travelers and families (with children). Only a couple of mins walking from Lake Memphremagog, and 5 mins driving from Mont Orford Ski Resort. Free WiFi and Free Parking. Wood floor, full kitchen, 1 bathroom/amenities, washer, dryer, dishwasher, wood burning fireplace, big terrace and BBQ.

Guest favorite

A winding gravel path leads through lush greenery, bordered by natural stone. Tall trees provide shade while a grassy area is visible in the distance. The scene is peaceful, inviting guests to explore the outdoor surroundings.

Guest suite in Newport

4.83 out of 5 average rating, 241 reviews

Lake View Studio

Cozy studio apartment with patio and yard that has a beautiful view of the international Lake Memphremagog. Dog & cat friendly. It is close to the Kingdom Trails, Burke Mountain, Jay Peak Resort and just a 10 minute drive to Canada (30 minutes to Magog, Quebec). Lots of opportunity for outdoor activities such as hiking, kayaking, mountain biking, fishing, sailing, skiing/snowboarding and more. Welcome to use the patio and fire pit (Please bring your own wood and buy local).

Guest favorite

The exterior of a two-story condo is surrounded by snow, showcasing a sloped roof and a welcoming red door. Bare trees provide a natural backdrop, with a glimpse of the mountain visible in the distance. Soft snow blankets the ground, creating a serene atmosphere.

Apartment in Jay

5 out of 5 average rating, 7 reviews

Absolute best ski on/off at Jay.

Location, location, location. This 2br Slopeside condo is position A on the snowiest mountain in the east. Inside, you'll find 2 bedrooms featuring a queen bed and a twin over full bunk. The kitchen comes fully equipped to make meal prep a breeze. The cozy living room has a gas fireplace to warm up or relax and enjoy an après drink. Our condos always feature complete linens, towels, and essential sundries because no one wants to lug that stuff to their vacation.

Top guest favorite

A spacious living area features a large area rug with nature-inspired patterns. Two comfortable sofas offer ample seating, complemented by a wooden coffee table in the center. Warm lighting is provided by a floor lamp, and a view of the kitchen and staircase is visible in the background.

Home in Jay

5 out of 5 average rating, 34 reviews

Location! Newly Renovated Ski-in/Out by Waterpark

Completely remodeled in 2024. Ski-in / Ski-out. Cannot beat the location! Steps to the water park, ice rink, tram, restaurants, and bars. Enjoy an upscale two story, 3 bed, 2 bath family-friendly luxury condo with a private back deck & small yard. You do not have to use your car at all. Quiet corner unit with no one above or below you. Each guest will be given a unique door code prior to check-in. Kitchen & linens are very well stocked. Well behaved dogs welcomed.

Guest favorite

Home in Lowell

4.93 out of 5 average rating, 122 reviews

Tranquility Lodge Vermont

Luxury awaits in this custom crafted 4000’ log-home, offering 5 bedrooms 4 bathrooms. 360 views of the Jay Peak valley. This gem of a rental is just 12 miles from Jay Peak Resort. Need more space? Inquire about additional on site Treehouse and Cabin rental. Pets welcome with collection of pet fee prior to arrival. All guests required to be in compliance with Vermont state guidelines related to travel during COVID-19.

Guest favorite

Two Adirondack chairs are positioned beside a serene pond, providing a peaceful spot to enjoy the view. Lush green grass surrounds the water, with rolling hills and mountains visible in the background under a clear sky.

Apartment in Troy

4.98 out of 5 average rating, 176 reviews

Jay Peak Getaway

Clean and cozy apartment with private entrance and parking space. Located minutes from Jay peak ski lifts, local biking & hiking, Newport shopping and Canada. Located on a 10 acre parcel with spectacular views of Jay Peak mountain range. Outdoor enthusiasts will love the many activities available in Winter or Summer. Easily accessible off route 100 on a paved road. Owners are on site and available if needed.

Top guest favorite

A cozy cottage exterior is set among lush greenery, featuring a wooden deck that wraps around two sides. Large windows are visible, allowing natural light into the inviting interior. Surrounding trees create a tranquil atmosphere in the well-maintained front yard.

Cabin in Brome

4.98 out of 5 average rating, 110 reviews

"Le Shac" a bit of paradise awaits you

WINTER or SUMMER...... well-insulated with a gas fireplace & electric back up, this is a perfect cottage for nature lovers! 20-30 min. to Sutton, Bromont or Owls Head ski areas.Enjoy this unique and tranquil country get-away with close proximity to the villages of Sutton & Knowlton. We offer a beautiful view, toboggan hills:) , snowshoeing, & x- country skiing space! Nature at its finest!