Holiday houses in Frederick County

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Top-rated holiday rentals in Frederick County

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Guest favourite

Apartment in Capon Bridge

4.99 out of 5 average rating, 114 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.

29 Oct – 5 Nov

$1,087 AUD total

Guest favourite

Home in Winchester

4.97 out of 5 average rating, 166 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 !

5 – 12 Nov

$1,687 AUD total

Guest favourite

Apartment in Winchester

4.87 out of 5 average rating, 154 reviews

Downtown FUN! Personal Mid Century 2bd Apartment!

Welcome to Blossom! Your own, private pied-à-terre, located in Winchester's historic district, 1 block from the Old Town Walking Mall! Blossom's UBER-LUX upgrades include a fully-stocked custom kitchen, marble countertops, new stainless steel appliances, high speed internet, gleaming hardwood floors, queen size canopy beds, heavenly memory foam mattresses, 50' smart TV, all delivered with a Euro MCM flare! Blossom is ideal for a romantic getaway, smart business travel, or a quick City escape!

24 – 31 Aug

$1,597 AUD total

Guest favourite

Apartment in Winchester

5.0 out of 5 average rating, 138 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.

31 July – 7 Aug

$2,122 AUD total

Guest favourite

Apartment in Winchester

4.98 out of 5 average rating, 217 reviews

Downtowner

No hassle parking on premises and a private entrance. The "Downtowner" is a 1920's era restored home in a quiet residential section of Winchester's Historic District and just a short stroll to the downtown "pedestrian only" walking mall with restaurants, cafes, and shops. Clean and spacious, the apartment is complete with bed linens, towels, etc. and stocked with water in the fridge as well as a Keurig with coffee options, tea, hot chocolate, etc...Xfinity HDTV with voice remote control.

24 – 31 Aug

$1,414 AUD total

Guest favourite

Cottage in Winchester

4.9 out of 5 average rating, 99 reviews

Lockley Cottage at Historic Perry Farm

Peace and tranquility await you at a quaint cottage on historic Perry Farm, where the original 19th century farmhouse still stands today. Stroll several acres of land and enjoy pastoral views while you unwind at this peaceful historic property in the hills of northern Shenandoah Valley. This rural retreat is easily accessed from I-81 and located a short 10-minute drive from historic downtown Winchester. Enjoy local wineries, breweries, farm markets, and the renowned Apple Blossom Festival.

14 – 21 Sept

$1,065 AUD total

Guest favourite

Apartment in Winchester

4.94 out of 5 average rating, 272 reviews

Downtown 1920's Gas Station

Luxury 1920’s Refurbished Gas Station repurposed into a beautiful apartment. Private off-street parking/EV car charging station, full kitchen, custom shower with rain system, super high speed wifi, smart TV & Blu-Ray. Plenty of light with frosted garaged doors. AC/Heat, Washer/Dryer, Dish Washer, coffee nook, and open living design. Be a part of Old Town Winchester in this unique fun space in walking distance to breweries, neighborhood Pizzoco Pizza parlor and the downtown walking mall.

16 – 23 Aug

$1,933 AUD total

Guest favourite

Home in Inwood

4.89 out of 5 average rating, 549 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.

13 – 20 Dec

$1,022 AUD total

Guest favourite

Apartment in Winchester

4.8 out of 5 average rating, 287 reviews

Pretty Little Apt by the Train II

This little place is just plain charming. Lots of light and personality. Wonderful alternative to the typical hotel experience. Fabulous for short term rental needs. Come enjoy Downtown Flat screen TV/ Record Player FREE PARKING/WIFI Near Piccadillys Pub, the Walking Mall, our beautiful and historic library, Shenandoah Univ. -5 minute Winchester Med Center -5 min DC. -1.5 hr Skyline Drive -30 min Free Parking too ! Reach out on social media if you need more. Michele Bouve Hoffman

19 – 26 Apr

$1,301 AUD total

Guest favourite

Home in Winchester

4.97 out of 5 average rating, 213 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.

21 – 28 Jan

$1,365 AUD total

Guest favourite

Cottage in Winchester

4.97 out of 5 average rating, 424 reviews

Emma's Stone Cottage

Relax and unwind in the privacy of this wonderful stone cottage, which sits on 15 beautiful acres. In addition, it is located only 2.5 miles from I-81 and 14 minutes from Winchester Medical Center, Old Town Winchester, Shenandoah University and much more. Our cottage is fully furnished with all the comforts of home. From the full kitchen, central air, water softener, HD smart televisions, Wifi, outdoor firepit and more. It has everything you need for a peaceful and enjoyable stay.

11 – 18 Apr

$1,559 AUD total

Superhost

Cabin in Capon Bridge

4.78 out of 5 average rating, 313 reviews

WV Mountain cabin

Beautiful cabin with perfect mountain views and private setting. This is a great cabin for reconnecting with your friends and family or a romantic getaway. The cabin is located on 5 acres of woods for you to explore.Has parking for up to 3 vehicles. A 4-wheel (SUV, pickup Truck) is required in winter months & in snow for access to this mountain ridge cabin! Sparkling clean, well maintained space. Maximum 5 guests, 2 queen beds plus a futon. Dog friendly w pet fee.

9 – 16 June

$1,352 AUD total