
Holiday houses in Monterey
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Top-rated holiday rentals in Monterey
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The Hogshead Cabin
Peaceful retreat nestled on a 118 acre farm! Authentic 1850's log cabin reconstructed with modern amenities (fiber internet!) for a dream vacation spot. Completed fall of 2023 - brand new elegance with rustic charm. Enjoy hiking/fishing nearby, visit charming towns of McDowell/Monterey or take a short ride to Snowshoe or The Homestead. Enjoy fires in the fire pit or fireplace, sunsets over Bear Mountain, and panaromic views. Escape regular life and relax! Owners nearby for anything you need.
5.0 out of 5 average rating, 77 reviews
Malcolm Place
Leave the day-to-day behind & enjoy the beautiful view, the wildlife and all the fun of Highland County! Malcolm Place offers a quaint retreat with three bedrooms and one and half bathrooms, situated along a serene mountain range. Experience the joy of fly fishing, hiking, and relaxation all available right in beautiful Highland County. Pet friendly. Check Out out FB and IG 20 mins to downtown Monterey 55 mins to Stanton 1 hour to Omni Homestead Resort and Spa 15 mins to Sounding Knob Fire Tower
5.0 out of 5 average rating, 10 reviews
Serenity by the Stream
Cabin in the Shenandoah Mountain surrounded by National Forest on 3 sides. Inside cozy atmosphere with warm lighting and local landscape art throughout. Bright and cheery in the bedrooms best suited for 2-4 adults or family with children. Wonderful sound of the river throughout the property. Step outside to hundreds of miles of biking and hiking trails, and stocked lakes and streams. Well maintained paved state road to cabin driveway. The house is 20 minutes West of Harrisonburg VA and JMU.
4.99 out of 5 average rating, 535 reviews
Blue View Lodge
Terrific mountain view with a short walk to the middle of town. Relax, refresh, explore the mountains, or, if you must, work in this town and country cottage with good fiber internet, WiFi, cell service. 3 bedrooms-- 1 w queen bed, 1 w double, and 1 w bunk bed w 2 doubles. Updated kitchen, 2 full baths one new with tub, one updated with large walk in shower. Bonus sunroom Roku TV; BluRay DVD Nearby hiking, fishing, hunting. 10 minute walk or 1 minute drive to shops and restaurants.
5.0 out of 5 average rating, 33 reviews
Retreat to entire home,hot tub, sauna, fish, hike
Bring the whole family to this entire home with lots of room for everyone. Outdoor ping pong, hot tub, and view of creek in the back yard. There is 155 acres for hiking. Stay connected still with Wi-Fi . Full kitchen, washer and dryer, large grill on deck. Cozy fire place inside and pool table. The master bath has large soaking tub and dry sauna. Home is 20 minutes from Monterey. Home is 42 miles from snow shoe ski resort and 32 miles from cass scenic railroad. Recreational area 17 miles.
4.89 out of 5 average rating, 73 reviews
Doe Hill Escape
Read this entire listing as Doe Hill is a very remote location. Please note this is an old farm house: No A/C, No Wifi, No Cell Service! Our home is one of 4 current family houses on an active working farm that has been in operation since the late 18th century. The home is rich in history but recent renovations make it quite comfortable. The large patio is perfect for watching the sunset over Jack Mountain or the moon rise over the Bullpasture. Clear nights are great for stargazing.
4.95 out of 5 average rating, 261 reviews
Brent's Cabin
Enjoy our cozy and comfortable cabin situated on 20 private wooded acres near several trout streams, George Washington National Forest, Virginia Game Commission, hiking trails, and caves. Brent's Cabin sleeps four, including a double bed and two twin beds in the loft. For skiing we are 1 hour and 30 minutes from snowshoe and 30 minutes from The Homestead. For fishing we are 5 minutes away from the Bullpasture, 10 minutes from the Cowpasture, and 25 minutes from the Jackson River.
4.96 out of 5 average rating, 295 reviews
Best views in Highland County !
Located in the pristine Mill Gap Valley. At night you can reach out and touch the stars. National Forrest is close by too. Enjoy the peace and tranquility that can only be offered in Highland county. The farm along with our Maple Syrup is certified Organic. From our apple trees to our hay and pastures. We are Organic! If you would like a tour of our farm or maple operation, let us know! By September 2020, there will be a new outdoor living area with a hot tub and dining.
4.99 out of 5 average rating, 569 reviews
Big Spring Bed & Breakfast
Ranch style house on 300 acre farm where the Cowpasture river runs through it. Nestled beside a Big Spring. Farm is bordered on the east by the George Washington National Forest. Short walking distance to the Shaw's Ridge Trail.Short driving distance to Shenandoah mountain and the Confederate breastworks. A few miles from historical McDowell and Monterey,Highland County,Virginia. Enjoy outdoor activities such as fishing hunting hiking biking kayaking in the area.
4.92 out of 5 average rating, 161 reviews
YEAGER HOUSE - On a Civil War Battlefield
Yeager House is a charming 3-bedroom cottage in Bartow, WV. Located on the site of a Civil War battlefield, Yeager House is close to the Green Bank Observatory, the Durbin & Greenbrier Valley Railroad, Cass Scenic Railroad in the historic town of Cass, Monongahela National Forest and Snowshoe Mountain Resort. Enjoy hiking, biking, fishing and the unsurpassed beauty of the Allegheny Mountains.
4.84 out of 5 average rating, 152 reviews
Craftsman Cottage - 45 minutes to Snowshoe
A century-old home in the small town of Durbin WV, the Craftsman Cottage is fully renovated with authentic bourbon barrel staves and stylish features throughout. You'll find the location of our house to be the perfect launchpad for every adventure around. Pocahontas County is well known for its hiking, biking, skiing, fishing, kayaking, history, train rides, and more.
5.0 out of 5 average rating, 140 reviews
Historical 1800s Cottage
Historical cozy cottage built in the mid 1800s conveniently located near the Green Bank Observatory, Snowshoe Mountain Resort, the National Forest and loads of hiking and biking trails. From the back yard, you can access hiking trails which connect to the Observatory's many hiking and biking trails. Cass Scenic Railroad and the Greenbrier River are only 6 miles away.
4.94 out of 5 average rating, 268 reviewsPopular amenities for Monterey holiday rentals
Other great holiday rentals in Monterey

Blue Grass Chestnut Cottage
4.96 out of 5 average rating, 79 reviews
Thorn Creek Cottage
4.98 out of 5 average rating, 47 reviews
Log Cabin | Hot Tub, Big Views, Dark Skies
5.0 out of 5 average rating, 8 reviews
The Turkey Roost ~ a peaceful mountain cabin
4.98 out of 5 average rating, 80 reviews
Tuckerman Retreat
4.86 out of 5 average rating, 65 reviews
The Boyer Camp House
5.0 out of 5 average rating, 32 reviews
The Farmhouse at Storybook Farm
5.0 out of 5 average rating, 3 reviews
Log Cabin Tiny Home
4.88 out of 5 average rating, 40 reviewsDestinations to explore
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- Timberline Mountain
- Snowshoe Mountain Resort
- Blackwater Falls State Park
- Canaan Valley Resort & Conference Center
- Wintergreen Resort
- James Madison University
- Canaan Valley Ski Resort
- White Grass
- Virginia Horse Center
- White Oak Lavender Farm & The Purple WOLF Vineyard
- Allegheny Springs
- Frontier Culture Museum
- Cass Scenic Railroad State Park
- Grand Caverns
- Massanutten Indoor WaterPark
- The Plunge Snow Tubing Park
- Douthat State Park
- Silver Creek
- Smoke Hole Caverns
- Gypsy Hill Park
- Family Adventure Park





