Vacation rentals in Gainesboro

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Top-rated vacation rentals in Gainesboro

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

Guest favorite

Apartment in Capon Bridge

4.99 out of 5 average rating, 111 reviews

Paw Paw Suite ~ 1 of 5 Unique Stays at Basswood

For those seeking to step away from the bustle of the city and slow down in a friendly, charming town. Basswood is a historic home that has been lovingly remodeled to include five private suites each with their own unique style. The Paw Paw Suite is an inviting space with a queen size bed, double shower bathroom, and kitchenette. Located in the heart of Capon Bridge, you'll find it easy to walk to everything. For a relaxing stay in a friendly, artsy community, this is a great place to enjoy.

Jan 14 – 21

€ 94 per night
Guest favorite

Apartment in Winchester

5.0 out of 5 average rating, 134 reviews

Old Town Loft In Highly Desirable Area Downtown

Location, Location! A completely renovated apartment in the highly desirable center Winchester. You’ll still be able to see some of its original character throughout this historic building. The apartment has a fully stocked custom kitchen with reclaimed wood and quartz counters, coffee nook with Keurig, large tile shower with glass doors, hardwood floors, queen memory foam mattress, high speed Wi-Fi, 50’ smart TV, Xfinity HDTV with voice remote control, AC/Heat, Washer/Dryer, and dishwasher.

Aug 6 – 13

€ 166 per night
Guest favorite

Home in Inwood

4.89 out of 5 average rating, 539 reviews

Arden House, Inwood WV

Ground level studio apartment. No steps. Completely separate entrance from main house. Private entrance and parking. There is an entrance room with a double bed, twin bed and sofa. In a separate living area, there is a queen bed, TV, private bath, desk, table, microwave, convection oven, air fryer, refrigerator Outside there is a large area to use outdoor gas grill, picnic table and fire pit. Dogs allowed and must be kept on a leash when outside. Please NO CATS. The owner is allergic.

Nov 23 – 30

€ 89 per night

Popular amenities for Gainesboro vacation rentals

Other great vacation rentals in Gainesboro

Guest favorite

Home in Winchester

4.97 out of 5 average rating, 210 reviews

City Charmer minutes from Old Town

Aug 20 – 27

€ 136 per night
Superhost

Cottage in Gerrardstown

4.85 out of 5 average rating, 279 reviews

Wooded Mountain Retreat near Creek

May 26 – Jun 2

€ 105 per night
Guest favorite

Guest suite in Winchester

4.79 out of 5 average rating, 272 reviews

Safe, cozy oasis with private living & bath.

May 30 – Jun 6

€ 86 per night
Guest favorite

Apartment in Winchester

4.98 out of 5 average rating, 214 reviews

Downtowner

Sep 3 – 10

€ 122 per night
Guest favorite

Tiny home in Linville

4.99 out of 5 average rating, 593 reviews

The spring house at Thistle Hollow

Jul 25 – Aug 1

€ 127 per night
Guest favorite

Apartment in Winchester

4.89 out of 5 average rating, 101 reviews

Modern Twist in Old Town! Rock n' Roll FUN!

Jul 22 – 29

€ 149 per night
Superhost

Cabin in Berkeley Springs

4.87 out of 5 average rating, 131 reviews

Magical quiet cabin nestled in the woods

Sep 6 – 13

€ 159 per night
Guest favorite

Home in Winchester

4.91 out of 5 average rating, 23 reviews

Misty Meadow has quite setting in the country.

May 17 – 24

€ 97 per night
Guest favorite

Cottage in Winchester

4.89 out of 5 average rating, 95 reviews

Lockley Cottage at Historic Perry Farm

Sep 7 – 14

€ 90 per night
Guest favorite

Apartment in Winchester

4.96 out of 5 average rating, 45 reviews

Newly repurposed Historic Home in Winchester VA!

Jul 14 – 21

€ 111 per night
Guest favorite

Guest suite in Clear Brook

5.0 out of 5 average rating, 37 reviews

Bluebird Bungalow

Apr 30 – May 7

€ 116 per night
Guest favorite

Cabin in Winchester

4.89 out of 5 average rating, 55 reviews

Kona's Cabin — Pet Friendly, King Bed, Fireplace

Sep 2 – 9

€ 181 per night

Destinations to explore

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