House vacation rentals in Winchester

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Top-rated house rentals in Winchester

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Guest favorite

Home in Inwood

4.88 out of 5 average rating, 603 reviews

Arden House, Inwood WV

Ground level two room unit. No steps. Separate entrance from main house. Private entrance and parking. There is an entrance room with a double bed, twin bed, sofa and full refrig.. In a separate living area, there is a queen bed, TV, bathroom, desk, table, microwave, convection oven, air fryer, gas fireplace. No oven. 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.

Guest favorite

Home in Inwood

4.97 out of 5 average rating, 129 reviews

Lindas Country Cottage

Come and relax in our Little County Charmer If needed for extended t. Under 2 miles from Interstate. 15 min from Charlestown Casino and horse racing. JD’s Fun Center with pool for children. ..2 hrs from Massanuttan . Take a ride to Historic Berkley Springs Or Harpers ferry.. Home is in a quite neighborhood. Tv Wi-Fi. Home is close to dining and fast foods delivery. So if you wanna feel right at home while visiting or town stop by and pay a visit at our small home with a little country charm

Guest favorite

Home in Bolivar

4.96 out of 5 average rating, 236 reviews

Newly renovated - Walk to Harpers Ferry NP

This stylish apt with fenced yard is located just mins to the HFNP Park. 24/7 convenient store just 1 block away; library across the street; a corner lot in a very quiet neighborhood. Perfect place to start your hikes or just to rest for the weekend. The home has 1 BR, kitchen, full bath and coffee bar - Keurig; coffee pot; coffee press; pour over coffee; beans and grinder; teas bags w/ water pot and private parking for our guests. Please note that the living area for this home is upstairs.

Guest favorite

Home in Winchester

4.97 out of 5 average rating, 190 reviews

Cameron Charmer pristine w/double master suites

Take a step into pure luxury in this newly renovated 1930's charmer in up and coming downtown area of Winchester. Owners have spared no expense to make this the kind of place where guests can come & forget about the rest of the world ! Incredible top of the line centralized dine in kitchen, wide open & inviting living areas, two master suites each with walk in closets & baths up lovely custom pine staircase. Come spoil yourself a bit at the Cameron Charmer, you are sure to enjoy your stay !

Guest favorite

Home in Edinburg

4.98 out of 5 average rating, 367 reviews

The Burrow ~ Our guest reviews say it all!

Indulge in a serene retreat at this charming countryside residence, perfect for a delightful getaway or a quick overnight stay. Just a 4-minute drive with two easy turns from I-81, this cozy home promises tranquility and relaxation. Begin your day on the inviting porch, soaking in the sunrise, setting the tone for a peaceful escape. Explore attractions such as hiking trails, enchanting caverns, or indulge in the local offerings of nearby wineries. A short stroll reveals Dee and Kenn's home.

Guest favorite

Home in Edinburg

4.98 out of 5 average rating, 437 reviews

Jay Birds Nest - Pet Friendly

Welcome to Jay Birds nest, located in the historic town of Edinburg, Virginia. Just 1.5 miles from I-81. Fully equipped with all the comforts of home and gorgeous mountain views. Enjoy having the entire house to yourself with sleeping for 6 with 2 queen bedrooms and 1 full bedroom and one full bath. Plenty of parking with room for two cars, one under a car port. Have your morning coffee in the relaxing sunroom or in the outdoor seating area. Just a quick walk away from the Shenandoah River.

Guest favorite

Home in Winchester

4.97 out of 5 average rating, 236 reviews

City Charmer minutes from Old Town

Renovated 1950's cottage style home. Enjoy a small house with a great front porch and large backyard with patio. Just minutes to drive and about 10-15 minutes to walk to Historic Old Town Winchester which includes numerous restaurants, bars, shopping, and often some kind of event like the Shenandoah Apple Blossom Festival! Our house is located about 65 miles West of Washington D.C. if you're looking for a day trip to the big city or just sit back and relax right here in our small town.

Guest favorite

Home in Winchester

4.94 out of 5 average rating, 140 reviews

Historic District Charm On Cameron Street

Charming home located in the historic district of Winchester. A short walk to the walking mall,restaurants, shopping, farmer's markets,breweries and more. Convenient to Shenandoah University, Winchester Medical Center, many museums including the Museum of the Shenandoah Valley, George Washington Hotel, Skyline Drive, 81 and more. Big deck and a half court basketball in the back yard. We have added a work/office area with a desk and chair ideal for working or schooling from home.

Guest favorite

Home in Edinburg

4.95 out of 5 average rating, 173 reviews

Charming, Parkview Cottage, King bed, 1 mi to I-81

Welcome to Parkview Cottage you will love this Cozy, 1940's home for a quiet fun getaway or quick overnight stay located in small rural town with an easy 1 mile from I-81. Enjoy quiet mornings on the porch watching the sunrise and a few neighbors stroll by out on morning walks and then venture off for the neighboring park, a hike, canoe trip, trip to the caverns or wineries close by. Enjoy the sunset from the sunroom over Edinburg Park. Park under the oversized "2 car" carport.

Guest favorite

Home in Winchester

4.94 out of 5 average rating, 167 reviews

Indigo Blue modern open vibe on tree lined street

Come stay in this lovely spacious downtown home located on a beautiful tree lined street. Enjoy its open mid century modern style and relaxing outdoor areas! This 3BR 2BA home w/ sunroom w/ gas fireplace & rear fully fenced courtyard is the perfect place get away to & explore downtown Winchester. Walking distance to everything. Park & walk & enjoy nearby John Handley HS /walking mall /shopping/live music /art galleries/ walk to the iconic Handley Library, You will LOVE it!

Guest favorite

Home in Strasburg

4.9 out of 5 average rating, 239 reviews

Shenandoah Siesta

PET FRIENDLY! Located in downtown Strasburg, just 15 minutes away from Front Royal and Skyline Drive, the Shenandoah Siesta House is a great get away for anyone looking to go hiking in the mountains, visit local Virginian wineries, or visit historical sites. It's a quiet house walking distance from restaurants and shops downtown. Great screened in porch makes you feel like you're staying in a treehouse. Beautiful view of sunsets at night.

Guest favorite

Home in Winchester

4.96 out of 5 average rating, 108 reviews

Aunt Tim's Farmhouse

Our farmhouse is located approximately 5 miles west of Historic Winchester, VA. The house is situated on 106 acres of an operational farm. You may see family members and friends tending honey bee hives, working in the detached garage, gardening, and completing other farm chores. The house is solely occupied by our guests. Come on out to enjoy some peace and quiet and take advantage of all Mother Nature has to offer!