Holiday houses in Fairplay

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Top-rated holiday rentals in Fairplay

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

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Top Guest favourite

Place to stay in Berkeley Springs

5 out of 5 average rating, 45 reviews

Unique A Frame - Hot Tub, Fire Pit, Cold Plunge

AlineRating, 5 stars2 weeks ago

This is a dream place. Everything was well designed with good taste on appliances, decor, furnitures, linens… You have the feeling of being in a magazine model house. You have everything you need and more! I stayed in contact with Danielle who didn’t measured efforts to quickly give any extra support that we needed. Thank you! The window view was stunning, the bathtub well cleaned, and all the kitchen utensils in great condition. We will definitely come back!

Guest favourite

Cottage in Middletown

4.9 out of 5 average rating, 273 reviews

Charming "Cream of the Crop" Cape ~❤️of Middletown

JesseRating, 5 stars1 week ago

Heather was amazing. Very responsive and answer all questions I had right away. Her home was amazing it was like home away from home. I would recommend heather anytime. Best air bnb host yet. I would highly recommend people to check this property out you will fall in love. Thanks heather for everything. Your home was very clean and welcoming.

Guest favourite

Cottage in Leesburg

4.92 out of 5 average rating, 406 reviews

Romantic Stone Cottage Circa 1869-75 acres to Hike

DawnRating, 5 stars3 days ago

We went for our anniversary desiring a quiet getaway and just as in the past, Reagan and Donnie delivered with the Stone Cottage! Such a peaceful place tucked away in the hills and yet so close to civilization. This house has character with history that you can see. Thank you again!

Guest favourite

Cabin in Great Cacapon

4.9 out of 5 average rating, 203 reviews

Cabin Getaway: Hot Tub ☆ Privacy ☆ Views

AshleyRating, 5 stars2 weeks ago

Such a peaceful location. We had a wonderful stay. The place was clean. We didn’t have any issues with check in or check out. The hot tub was great to relax at night. The space Is a good size for 2 couples looking to get away. The kitchen was stocked with pots and pans for cooking breakfast, lunch, and dinner. It’s only a short drive into town which has shops, restaurants, and the springs. Make sure to visit Charlottes Cafe. Best breakfast i’ve had in a long time. My son and family can’t wait to go back. When we pulled out the drive way to take the trip back home my son said he missed the house already.

Superhost

Guesthouse in Middletown

4.9 out of 5 average rating, 39 reviews

Riverfront Oasis with Mountain Views, Near Town

KimberlyRating, 5 stars2 weeks ago

Loved our stay! We were here from DC mainly to hike and relax and the space was perfect for both! Location is close to the north entrance of Shenandoah National Park which was wonderful. We cooked most meals in the unit and it was well equipped for basic meals. Beds were comfy, AC/heaters worked great, and the views were spectacular. Host was lovely and quick to respond. Would definitely stay again!

Superhost

Cabin in Berkeley Springs

4.87 out of 5 average rating, 159 reviews

Magical quiet cabin nestled in the woods

HeatherRating, 5 stars1 month ago

We loved the home and thoroughly enjoyed our stay. Aram was very responsive. There are lovely bird feeders on the deck that can be filled with provided birdseed and we observed many beautiful birds attending the feeders! The kitchen has everything you'll need and was clean and spacious. The firepit was peaceful and there is a path to do a 5-8 minute hike that starts right out the back door and goes around their property to observe nature. We visited the Himalayan Salt Cave in town and found it very relaxing and unique! There are many unique and fun shops to visit for souvenirs and other gifts. The only drawback we noted about the entire stay was having to drive 12-15 minutes to get out to the main road if we needed to run out to grab something - but that was listed in the property description, so we tried to plan ahead and get everything we needed in advance to avoid side trips.

Top Guest favourite

Cottage in Capon Bridge

5 out of 5 average rating, 26 reviews

*New* River Front Retreat *HotTub-FirePit-Kayak*

AllisonRating, 5 stars1 week ago

We loved our stay at Hummingbird Hideaway. The easy river access from the backyard is the best part. The yard is awesome for playing with the dog (or kids) and the property has so many amenities not even mentioned in the listing. We loved the locking gate on the deck to keep our dog contained. The home itself is very clean and well organized. It also had so many details we rarely see at other homes we have rented, such as extra hooks in all the places you'd need them (front door, restrooms, hot tub area, shower, etc), toiletries, extra soft throw blankets and pillows, and a welcome pack of snacks/treats/toys for both humans and dogs! The kitchen is very well equipped as well. The (very friendly) neighbors are within shouting distance but the property is spacious. Although the house isn't secluded it still feels private & cozy. Stephanie was an excellent host. Very friendly, proactive and accommodating. We're already planning a (longer) future visit!

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Other great holiday rentals in Fairplay

Guest favourite

Apartment in Georgetown

4.87 out of 5 average rating, 119 reviews

Cozy Modern Apt. In G-Town

Line And BenjaminRating, 5 stars2 days ago

We had a great stay! Perfect location in Georgetown, and excellent communication with the hosts!

Guest favourite

Home in Mercersburg

4.93 out of 5 average rating, 40 reviews

Gorgeous Mountain Home at Whitetail Resort

AlviraRating, 5 stars3 months ago

Went on a trip with our family after many years and was so glad to choose this place as our getaway — we loved the home and can’t wait to get back. The hosts were extremely kind and helpful, their home was comfortable for all ages.

Top Guest favourite

Home in Gettysburg

4.96 out of 5 average rating, 114 reviews

East Cavalry Red House

MikaylaRating, 5 starstoday

We were in town for a wedding, the house was very nice and clean. Our only issue was we wish there was at least 1 more TV somewhere in the house. There is only 1 provided down in the basement and we had to use that room as a bedroom so no one else was able to watch tv. Other than that we enjoyed everything!

Guest favourite

Home in Cross Junction

4.87 out of 5 average rating, 125 reviews

The Little Red Schoolhouse

CatharineRating, 5 stars1 week ago

SUCH a cute place! Super clean inside and out! The hot tub was perfect and ready to go when I got there. It's also an easy commute to Winchester and farmers markets. Perfect for a girls night or a couples get away.

Guest favourite

Cabin in Berkeley Springs

5 out of 5 average rating, 24 reviews

Gorgeous Log Chalet/Cabin with Hot Tub

ScottRating, 5 stars6 months ago

Great stay at a wonderful cabin nestled back into the woods. Well furnished and maintained with a phenomenal deck and screened patio.

Superhost

Home in Harpers Ferry

4.83 out of 5 average rating, 248 reviews

Larger Families, Hot tub, Campfire Ring, Rural

AdrienRating, 5 stars1 month ago

Home was clean and as described. It was large and roomy. Outside had a nice yard to play in. Harper’s Ferry town and the national historic park are amazing places to visit. Lots to do and see even in March. I would visit again and stay at this home again.

Guest favourite

Condo in Bethesda

4.89 out of 5 average rating, 190 reviews

Bright 2br w amazing loc and view

NeilRating, 5 stars2 weeks ago

Great location, everything clean, Mark is incredibly responsive, and he clearly pays a lot of attention to keeping the apartment stocked with everything a guest needs. For example, when we used the stove top, there was a great selection of pans, there was a potholder right there, all the cooking utensils we needed, dish soap, a drying rack, etc. It may seem like a little thing, but it’s representative of the entire apartment. If there’s something you need and hope is there, it’s there. Great stay.

Top Guest favourite