Guesthouse vacation rentals in Montgomery County

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Top-rated guesthouse rentals in Montgomery County

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

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Guest favorite

Guesthouse in Collinsville

4.96 out of 5 average rating, 654 reviews

5 Star Apartment (1000sf) w/Garage(NoCleaningFees)

This 5 Star private guest suite located in Henry County, VA is separate from the main house. The apartment is 1000 square foot of living space. The new addition has beautiful granite countertops, ceiling fan, and a large bathroom with a ceramic walk-in shower. Great neighborhood, this in-law suite is about 40 miles from the Blue Ridge Parkway and 20 minutes from the Martinsville Speedway. Philpott Lake is 8 miles away. Industrial Park is less than 2 miles away. It is 8 minutes from SOVAH.

Guest favorite

Guesthouse in Dublin

4.98 out of 5 average rating, 42 reviews

Claytor Lake Pool House

Relax and unwind in our spacious guest house. Step out of the door onto the beautiful full size, in- ground pool deck, open late May to early September. Well appointed kitchen with everything you need to cook a full meal or just a quick snack. About 3 minutes to Claytor Lake State Park for hiking, swimming or boating with Mountain View's. We have parking for your boat on the property. We live in a log home on the property and are usually available by text or in person. Easy access to I-81.

Guest favorite

Guesthouse in New Castle

4.94 out of 5 average rating, 121 reviews

Waterfront Cottage Retreat with Hot Tub

"Refined with a Touch of Wild". Enjoy our country retreat minutes away from the East Coast's famous Blue Ridge Appalachian Trail & the Roanoke Valley's finest dining spots; or stay home for a home cooked meal adjacent to our unique waterfall patio. The Stonebridge Cottage is a private guest house offering the perfect mix of cozy & country with a resort-like finish. This property is part of the Sak's House Creek Retreat and can be reserved with the main house which sleeps up to 14 (9 beds).

Guest favorite

Guesthouse in Blacksburg

4.94 out of 5 average rating, 551 reviews

*Guest Cottage, wooded, open and airy loft style !

*Open living, dining and lounge area! Smart TV and foosball! *Wooded setting in country neighborhood. *15 minutes to VT, 25 to RU. *Large kitchen equiped to host 8-10 guests. *Open loft area with sleeping for 8. Also additional room with full bed for extra space/privacy. *2 Full baths *Main house next door available to book. *Please Note! Although we treat for Pest Control, Clean up all crumbs as best as possible! Absolutely no smoking or recreational drugs on the property!

Guest favorite

Guesthouse in Roanoke

4.88 out of 5 average rating, 119 reviews

Boho Bungalow

Book a stay at the Boho Bungalow and enjoy the best of what Roanoke has to offer. This guesthouse is nestled in a private setting with trees and a privacy fence surrounding the house with a gravel driveway and parking space. Stay in and watch TV, play games, read books, enjoy the outdoor patio, or make a delicious meal with the fully stocked kitchen. If you want to explore the area, the Bungalow is less than 10 min from downtown Roanoke, as well as local shopping and restaurants.

Guest favorite

Guesthouse in Blacksburg

4.99 out of 5 average rating, 78 reviews

Little Red Farm: Two Bedroom Guest House-Mt Views

Relax with family and friends on Little Red Farm. Situated on 4 acres with beautiful mountain views on a private country road. Morning walks will be greeted with nature's beauty surrounded by working farms. 1 mile from Prices Fork Rd and only 3 miles from VT Campus. Centrally located for local events, Little Red Farm provides the perfect space to relax and unwind. Owner's residence on site gives you the peace of mind of that you will have everything you need during your stay.

Guest favorite

Guesthouse in Blacksburg

4.89 out of 5 average rating, 285 reviews

Cottage in Blacksburg, Virgini

Cottage with one bedroom with king size bed, full bathroom, fully furnished kitchen with stove, refrigerator, dishwasher, microwave, dishes, pots and pans, etc. Living room with queen sleeper sofa with flat screen tv. Huge (450 sq. ft.) deck overlooking Ellett Valley, Approximately 3 miles from Blacksburg No smoking. Cats and dogs OK. Cottage and loft can be rented as a combination or separate as they are on the same unit but have separate entrances. NO barking dogs!

Guest favorite

Guesthouse in Roanoke

4.93 out of 5 average rating, 979 reviews

The Gardener's Cabin at Bent Oaks Manor

The Gardener's Cabin is the perfect "pitstop" centrally located in Roanoke's historic Old Southwest District, approximately one mile from the center of Downtown Roanoke. It provides up to two guests with a safe, private and convenient place to spend a night or two while enjoying Roanoke. This 200 square foot bungalow is situated in a secluded courtyard behind Bent Oaks Manor and once housed the family's gardener when the property was built in 1910. Dog friendly, but no cats!

Guest favorite

Guesthouse in Riner

5 out of 5 average rating, 371 reviews

Travelers' Rest Guesthouse

Cozy, well appointed house is perfect for a get-away weekend in the mountains, a football weekend at Virginia Tech, graduation events at Radford University, or to use as a family retreat in the beautiful countryside of Virginia's New River Valley. This small 2 bedroom/1 bath guest house has a kitchen with full sized appliances. Queen sized bed in first bedroom, two twin sized beds in 2nd bedroom. Stacked washer & dryer in bathroom.

Guest favorite

Guesthouse in Woodlawn

4.93 out of 5 average rating, 120 reviews

Adorable 1-Bed Tiny House w/Outdoor Living Area

This 400 sq ft tiny house is nestled in between rolling hills and beside a small creek. Gorgeous views of pasture and hills behind the house. You'll be surprised at how open the living space feels. Extra high ceilings and plenty of windows provide a bright and spacious atmosphere. Our home was a finalist in Apartment Therapy's Tiny Space contest. We lived here for a year while we remodeled our main house, also on property.

Guest favorite

Guesthouse in Willis

4.91 out of 5 average rating, 151 reviews

Hog Mt Retreat by Buffalo Mountain Getaway

This cozy retreat is the perfect retreat for two or even three. Situated less than a minute from the Blue Ridge Parkway, it's the perfect location to relax and enjoy the area. Floyd, VA and Mt. Airy, NC are less than 30 miles away. Please note that AT&T has limited service in our area. We provide a landline for your convenience. We always offer fresh, clean, commercially washed linens for your stay.

Guest favorite

Guesthouse in Salem

4.9 out of 5 average rating, 21 reviews

Garage Apt 30 min VT/15 Roanoke College

30 minutes from Virginia Tech, 15 min from Roanoke College. INDEPENDENT entrance. 800 square feet. 2 QUEEN size beds, one being a nice pull out sofa bed. Extra mattress on floor available. Kitchen (with dishwasher), washer/dryer, full bathroom, cable TV. Carpet and tile. Secluded residence on 25 acres of woods. 8 minutes by car to Walmart. Message me for specific requests!