Guesthouse vacation rentals in Jefferson County
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Jefferson County
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Jefferson County guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Smithsburg
4.97 out of 5 average rating, 645 reviewsJewel Vinsota Artist's Guesthouse
Nov 16 – 23
Guesthouse in Keedysville
4.98 out of 5 average rating, 190 reviewsCity Dog Farm
Jul 9 – 16
Guesthouse in Middletown
4.95 out of 5 average rating, 246 reviewsIndulge, Fresh Flowers, Frederick County Haven
Oct 23 – 30
Guesthouse in Frederick
4.97 out of 5 average rating, 316 reviewsThe Shady Bear Cabin
Feb 14 – 21
Guesthouse in Front Royal
4.88 out of 5 average rating, 253 reviews"Cabbin" at Mountain Home B&B
Aug 10 – 17
Guesthouse in The Plains
4.87 out of 5 average rating, 79 reviewsStylish 1 Bedroom Studio Middleburg
Oct 17 – 24
Guesthouse in Berkeley Springs
4.83 out of 5 average rating, 288 reviewsTerrapin Cabin. A sunny, quiet cabin in the woods.
Jun 14 – 21
Guesthouse in Hagerstown
4.87 out of 5 average rating, 23 reviewsValentia farm guest cottage
Feb 10 – 17
Guest house rentals with a patio
Guesthouse in Lovettsville
4.94 out of 5 average rating, 122 reviewsThe Patent House
Dec 27 – Jan 3
Guesthouse in Myersville
4.93 out of 5 average rating, 192 reviewsSpruce Run Cottage, Farm stay on Catoctin Mountain
Jul 14 – 21
Guesthouse in Bluemont
4.97 out of 5 average rating, 102 reviewsBlueridge Mountain Guest Cabin- Amongst the Trees
Jan 10 – 17
Guesthouse in Front Royal
4.9 out of 5 average rating, 78 reviewsCozy Shenandoah River Cabin (10min to Nat’l Park!)
Mar 19 – 26
Guesthouse in Stephens City
5.0 out of 5 average rating, 6 reviewsVentura Cottage: 360-views/HotTub/4 acres/Gym
Nov 24 – Dec 1
Guesthouse in Middleburg
5.0 out of 5 average rating, 41 reviews18th Century Middleburg Cottage
Mar 30 – Apr 6
Guesthouse in Middletown
5.0 out of 5 average rating, 92 reviewsCottage, Pool, & Breakfast on 100ac Horse Estate
Jul 15 – 20
Guesthouse in The Plains
4.98 out of 5 average rating, 40 reviewsA lovely cottage in The Plains, Virginia
Nov 13 – 20
Guest house rentals with a washer and dryer
Guesthouse in Bluemont
5.0 out of 5 average rating, 309 reviewsSkyhorse Retreat Guest House
Oct 29 – Nov 5
Guesthouse in Berkeley Springs
4.97 out of 5 average rating, 288 reviewsPond Hill Guesthouse- 2 Bedroom w/Hot Tub & WiFi!!
Dec 17 – 24
Guesthouse in Hamilton
4.98 out of 5 average rating, 116 reviewsTrailside Chalet (A storybook chalet with hot tub)
Oct 5 – 12
Guesthouse in Waterford
4.92 out of 5 average rating, 121 reviewsCabin On The Creekside
Jul 26 – Aug 2
Guesthouse in Purcellville
4.94 out of 5 average rating, 72 reviewsThe Nest on Nixon Road
Nov 5 – 12
Guesthouse in Bluemont
5.0 out of 5 average rating, 56 reviewsBluemont Escape:Walk to Bears Den; Bear Chase Brew
Jul 8 – 15
Guesthouse in Leesburg
4.99 out of 5 average rating, 82 reviewsPrivate 2 BR, 1 Bath Carriage House Near Wineries!
Jun 8 – 15
Guesthouse in Frederick
4.97 out of 5 average rating, 31 reviewsBoutique space at Marble Ridge
Apr 15 – 22
Destinations to explore
- House rentals United States
- Guesthouse rentals United States
- Guesthouse rentals Washington
- House rentals Washington
- House rentals Deep Creek Lake
- Guesthouse rentals Baltimore
- House rentals Baltimore
- House rentals West Virginia
- Guesthouse rentals West Virginia
- Rentals with an EV charger Jefferson County
- Rentals with breakfast Jefferson County
- Rentals with lake access Jefferson County
- Apartment rentals Jefferson County
- Cottage rentals Jefferson County
- Kid-friendly rentals Jefferson County
- Cabin rentals Jefferson County
- Rentals with a hot tub Jefferson County
- Private suite rentals Jefferson County
- Fitness-friendly rentals Jefferson County
- Rentals with outdoor seating Jefferson County
- Rentals with a patio Jefferson County
- Pet-friendly rentals Jefferson County
- Bed and breakfasts Jefferson County
- Family-friendly rentals Jefferson County
- Rentals with a washer and dryer Jefferson County
- Rentals with a fireplace Jefferson County
- Rentals with pools Jefferson County
- Waterfront rentals Jefferson County
- Farmstay rentals Jefferson County
- Monthly Rentals Jefferson County
- Rentals with a fire pit Jefferson County
- Rentals with a kayak Jefferson County
- House rentals Jefferson County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes