Apartment vacation rentals in Winchester

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Popular amenities for Winchester apartment rentals

Weekly apartment rentals

Guest favorite
Apartment in Hamilton
4.97 out of 5 average rating, 60 reviews

Goose Hill

JesseRating, 5 stars3 months ago
The place was charming, well stocked and very comfortable. The communication was great and we would definitely rent again.
Superhost
Apartment in Reston
4.86 out of 5 average rating, 28 reviews

King Size Bed - Reston Metro Apt

ErlinRating, 5 stars1 month ago
The apartment is everything you see. Close to Metro and Reston Town Center. Wegmans being in the same building is a short walk downstairs. Hassen is very responsive with any troubleshooting issues in the building.
Guest favorite
Apartment in Frederick
4.91 out of 5 average rating, 161 reviews

Your own "Tiny House"

ChristianRating, 5 stars1 week ago
Becky was wonderful from start to finish awesome little place to stay very clean and the area was beautiful thank you Becky for everything I will definitely be back!
Top guest favorite
Apartment in Downtown Frederick
4.98 out of 5 average rating, 134 reviews

Luxury Apt w/ King Bed; Market St Artists' Suite

DannieRating, 5 stars4 weeks ago
I had an amazing time at Ava’s place! The location is amazing, right on market street, with so many great restaurants/shops/bars all around! The Airbnb itself was very pleasant and super unique. Not only did it have great amenities, but the decor was really cool too. Ava was very responsive and helpful whenever I had a question, and the flexible checkout time was great after a long weekend out and about. Next time I’m looking for an Airbnb in Frederick, I’ll definitely be looking for this one. And I highly recommend this place to anybody looking for a place to stay in the area!
Guest favorite
Apartment in Downtown Frederick
4.93 out of 5 average rating, 97 reviews

Charming Historic Downtown Apartment…The Fox’s Den

DanaeRating, 5 stars2 months ago
We were in town for a wedding and the 3 of us college friends had a great stay. The place was spacious, comfortable and cute. Easy to walk around the area and see the town. Hosts were easy to work with an very accommodating.
Superhost
Apartment in Downtown Frederick
4.87 out of 5 average rating, 159 reviews

Trendy in The Heart of Downtown Frederick MD

AdamRating, 5 stars8 months ago
Misti's studio apartment here in Frederick is so great that I extended my stay multiple times. If you want privacy, comfort, cleanliness, and an incredible location in downtown Frederick I would recommend it to anyone. I could not have been more happy with my experience.
Superhost
Apartment in Waynesboro
4.69 out of 5 average rating, 26 reviews

Apt A, 3 bedrooms, Waynesboro, PA

DameyonRating, 5 stars5 months ago
Great host comfortable home.
Superhost
Apartment in Chantilly
4.9 out of 5 average rating, 41 reviews

Out of Africa

JamesRating, 5 stars6 months ago
This is my second review of the apartment and it couldn’t be more perfect for a short or long-term stay. Mary Kay and Brad are great hosts and quickly communicate for any question or need. The apartment has a nice separate layout with a comfortable bedroom, cozy living room and well-equipped kitchen. If I’m ever in the Northern Virginia area again I’ll happily stay here. Jim

Private apartment rentals

Top guest favorite
Apartment in Round Hill
5 out of 5 average rating, 59 reviews

Whole Garage Apartment with Blue Ridge Views

KatelinRating, 5 stars4 months ago
Cindy’s garage apartment was beautiful and well-stocked with all of the snacks and basics we could need. There’s even a dog washing station in the garage, and an electric car charger should you need. She provides a $25 gift certificate each night stayed to a local vineyard, brewery to restaurant, and there are many to choose from just a short 5-10 minute drive from the Airbnb! It was peak foliage when we went, and we had dinner at Magnolias at the Mill. We also checked out Bluemont Station Winery & Brewery, Bluemont Vineyard, Great Country Farms, Dirt Farm Brewing, and More Better (highly recommend!). All of these places were beautiful, dog-friendly and a short drive! If you are a light sleeper or want to sleep in, bring an eye mask as there is a large skylight right over the bed!
Guest favorite
Apartment in Front Royal
5 out of 5 average rating, 29 reviews

Mt. Apt. in wine country

EjRating, 5 stars4 weeks ago
Spectacular getaway in the Shenandoah area. Home was immaculately clean and well decorated. The electric fireplace is a nice touch. Location was private and quiet. Cindy was gracious host who helped us get checked-in when we arrived. Space was very comfortable. Location provides easy access to Front Royal, Skyline Drive, and Virginia wineries. We would stay again.
Top guest favorite
Apartment in Manassas
5 out of 5 average rating, 144 reviews

Manassas Luxe Stay - Aviation-Themed Modern Escape

LatrondaRating, 5 stars4 weeks ago
Our second time staying here and it was just as fun as the first time.
Superhost
Apartment in Frederick
4.87 out of 5 average rating, 15 reviews

Luxury Basement Apartment Suite

AlexRating, 5 stars8 months ago
Stay was exactly as described. Home was clean and had everything needed for a home base for work and camp for the kids. Jorge and John we very communicative and friendly. 100% would reccomend.
Top guest favorite
Apartment in Leesburg
4.99 out of 5 average rating, 185 reviews

The Quarters at Belgrove

BenRating, 5 stars3 months ago
We stayed 7 nights and really enjoyed our time at Kristy and Byron's property. The home and grounds were absolutely lovely. Kristy was very responsive to all my messages. Byron was prompt to address a problem in the bathroom (as in, fixed within the day). They provided a lovely assortment of snacks and their DVD selection was top-notch. I wish the weather had been warmer so that we could have made more use of the porch. Long story short, if you're looking to stay in the area, then this is the place for you. Thank you so much Kristy and Byron! We hope to come back soon!
Guest favorite
Apartment in Harrisonburg
4.92 out of 5 average rating, 37 reviews

Private, Pet-Friendly Apartment

GennaRating, 5 stars2 days ago
Fantastic experience! The area is peaceful and relaxing with gorgeous scenery! My dog enjoyed the expansive outdoor space, and I loved how quiet and private the apartment was. I highly recommend this spot!
Guest favorite
Apartment in Centreville
4.76 out of 5 average rating, 51 reviews

Luxurious Guest Apartment with Steam Room Shower

SooRating, 5 stars3 months ago
David & Lynn are wonderful hosts! My plans had changed, and I was happy to book their place again. It was one of the few bookings that felt like home. Thank you both very much for hosting me for my second stay. The In-Law Suite is great. Everything you need is there. My only recommendation is to have your own network cable to connect to the router if you are particular about the cable type and speed.
Guest favorite
Apartment in Warrenton
4.95 out of 5 average rating, 264 reviews

Entire Spacious Apartment with Private Entrance

CindyRating, 5 stars2 months ago
This was our second stay in this lovely apartment, and just as great as the first! Such a lovely place to be while we visited our family over the holidays. The pool table is a fun addition! Thanks, Carl!

Apartment rentals with a hot tub

Apartment in McGaheysville
4.84 out of 5 average rating, 250 reviews

Massanutten Cozy Condo with Hot Tub & Jacuzzi

VictoriaRating, 5 stars1 month ago
We really enjoyed Maya's place! She was so sweet and gave us a beautiful valentine's gift basket and ballon. I cannot wait to return to her beautiful home again! Thank you Maya for everything!
Guest favorite
Apartment in Shepherdstown
4.94 out of 5 average rating, 16 reviews

West Virginia Gold (lower unit)

KatieRating, 5 stars4 weeks ago
We had a lovely stay and will definitely return. The home is directly on the Potomac river with beautiful river views. The home is a split duplex and you have an adorable apartment all to yourself with a wood fireplace, 2 bedrooms, walk in shower, and direct access to the hot tub overlooking the water. You barely notice the upstairs apartment other than the occasional sounds of footsteps above. All tvs are smart tvs with steaming capability. The hosts are very friendly and have excellent restaurant recommendations! This is a hidden gem and a great deal!
Top guest favorite
Apartment in Mercersburg
5 out of 5 average rating, 19 reviews

Rockwell Suite #201 at the Inns at Whitetail

PeterRating, 5 stars3 weeks ago
I really liked it. You can walk to the slope in about 2 minutes, put your skis on and ride. Place was spacious and clean. Bed was comfy. And there is a huge 86” tv so you can lay in bed and be at the cinema! WiFi works. Ac and heat works. Great place!
Top guest favorite
Apartment in Grantsville
4.97 out of 5 average rating, 116 reviews

Yoder School Guest House with wifi and hot tub

JulieRating, 5 stars2 months ago
A much needed time for R and R after the holiday hooplah and Rhoda delivers. The little details allowed us to fully focus on relaxing. Meticulously clean, no noise, amd majes you ferl right at home. We will be bavk as soon as we can. The hot tub in the cold felt amazing.
Superhost
Apartment in Berkeley Springs
4.78 out of 5 average rating, 82 reviews

The Parlor Suite

MichaelRating, 5 stars4 weeks ago
The room was great, very cozy and homey while really feeling like a B&B experience. The jetted tub was very nice and being right across the street from Berkely Springs park was wonderful. Would definitely stay again when we’re back!
Guest favorite
Apartment in Nokesville
4.95 out of 5 average rating, 21 reviews

Couples countryside escape

KayleeRating, 5 stars3 weeks ago
Lovely place, beautiful views and very nice space. Good for a vacation.
Guest favorite
Apartment in La Vale
4.9 out of 5 average rating, 63 reviews

Sweet 68

DrewRating, 5 stars1 week ago
it was quick and easy. Kimberly has made sure checking in is fast and painless. and me and my wife had our 4 year old with us who we thought was pretty loud and Kimberly assured us that she was ok. nice little place. Will stay again if I'm in the area again.

Quick stats about apartment rentals in Winchester

  • Total rentals

    40 properties

  • Nightly prices starting at

    $30 before taxes and fees

  • Total number of reviews

    3.5K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

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