Apartment holiday rentals in Winchester

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Popular amenities for Winchester apartment rentals

Weekly apartment rentals

Apartment in Downtown Frederick
4.79 out of 5 average rating, 203 reviews

Modern Condo In Downtown Frederick

JosephRating, 5 stars1 month ago
Spacious “condo” really the entire lower floor of a restored older home Fantastic location - easy walk to the restaurants and shops in the historic district
Apartment in Harpers Ferry
4.63 out of 5 average rating, 38 reviews

Memory Lane

DominicRating, 5 stars10 months ago
This AirBnb hosted by Julie was perfect! The space was just what we needed as a little home base as we explored Harper’s Ferry and the surrounding area. Julie provided great recommendations in terms of places to eat. Would love to go back!
Guest favourite
Apartment in Charles Town
5 out of 5 average rating, 19 reviews

Upscale Walkup Apartment

MichaelRating, 5 stars1 month ago
Nice, clean place. Good location for that area.
Superhost
Apartment in Culpeper
4.92 out of 5 average rating, 13 reviews

Private 2/2 full baths very bright basement home

KariRating, 5 stars7 months ago
We had a lovely stay at Lili's place. It was very peaceful! We would definitely book again if we were in the area. Lili was very responsive to any questions we had.
Guest favourite
Apartment in Cumberland
5 out of 5 average rating, 10 reviews

Cozy King Bed Suite With A Kitchen & ClawfootTub

AlanRating, 5 stars1 month ago
I was born and raised in Cumberland and have always been familiar with Washington St. Probably the single most beautiful street in Cumberland. Love did an amazing job describing the building and all the amenities and local attractions. We would definitely stay there again. What a beautiful building. Thanks so very much for sharing your home with us. Alan
Guest favourite
Apartment in Mount Jackson
4.94 out of 5 average rating, 90 reviews

Condo at Bryce Resort

LynnRating, 5 stars1 month ago
I wish I could have stayed longer to enjoy this condo and more of the area. Beautiful and peaceful place to relax, enjoyed a couple of wineries but didn’t try the restaurants. I don’t ski but I’d love to watch the skiers in wintertime because it’s a great view of the slopes. Next time I’ll play golf and check out the restaurants in the area
Guest favourite
Apartment in Charles Town
4.73 out of 5 average rating, 120 reviews

2 Bed Condo at Abolitionist Ale Works #300

TimothyRating, 5 stars2 months ago
Second time I have stayed and I enjoy the location and the close by food and drink options. Very quiet for a downtown location. While they do not offer parking, free parking is just two blocks away. The street parking in from of Abolitionist makes it easy to unload.
Superhost
Apartment in Massanutten
4.76 out of 5 average rating, 50 reviews

Massanutten Summit 2BR, 2BA

RickeyRating, 5 stars5 months ago
My family and I definitely enjoyed our stay. This was our 5 year anniversary Christmas at massunutten and the location did not disappoint anyone. We enjoyed being on the mountain watching the skiers go up and come down the slopes. The kids enjoyed being close to all the snow activities. We are looking forward to rebooking and going back during the summer once all the new add-ons are done. Thank you Daniel

Pet-friendly apartment rentals

Superhost
Apartment in Basye
4.67 out of 5 average rating, 6 reviews

Ski/MTB/Golf Condo (#122) - Mountain views!

DavidRating, 5 stars7 months ago
Great location for riding. Our stay was great
Guest favourite
Apartment in Mercersburg
4.82 out of 5 average rating, 65 reviews

Ski🎿 & hike from front steps—Mountainside getaway

MarkRating, 5 stars3 months ago
I think this is the best slope side ski condo at Whitetail. The slopes are right outside the door and the place is cute, clean, and comfortable. We will be going back!
Guest favourite
Apartment in Gaithersburg
5 out of 5 average rating, 11 reviews

1 Bed/1 Bath/1Pkg Space|Dogs-OK

AlashleRating, 5 stars1 month ago
Yue’s place is great and especially quiet. It is conveniently located near grocery, pharmacy, and banks. The most attractive though is a lake close by that is great for walks. Everything worked well and Yue was very responsive- always asking if there is more she can do. I will definitely come back again. One caution is the flight of stairs so if you are elderly or have a bad knee, that might be a problem.
Top guest favourite
Apartment in Mercersburg
4.91 out of 5 average rating, 46 reviews

Whitetail Resort Ski-in/Ski-out slope side condo.

KayleeRating, 5 stars3 months ago
This air bnb was perfect for a weekend getaway to Whitetail resort. The unit is steps away from the slopes, and Renee was not only responsive and extremely helpful, but able to accommodate schedule changes to make our trip happen.
Guest favourite
Apartment in Mount Jackson
4.87 out of 5 average rating, 97 reviews

Bike,Hike,Relax in Lux! at Bryce Resort

DanRating, 5 stars3 weeks ago
This place is fantastic. It's comfortable in every way, charming, beautifully decorated, spacious, and spotlessly clean. It's even nicer than the photos suggest. The location right at the base of the slopes at Bryce is perfect. I'll definitely stay here again someday!
Superhost
Apartment in Downtown Frederick
4.78 out of 5 average rating, 9 reviews

Lark's Nest on Market

KathleenRating, 5 stars14 months ago
We very much enjoyed our stay and appreciated being able to bring our dog. It’s a great layout, well decorated, and the deck has a terrific view of the sunsets. Easy walking distance to the restaurants and Baker Park. We will be glad to return.
Guest favourite
Apartment in Manassas
4.85 out of 5 average rating, 66 reviews

Perfect Location Old town / walk to the metro

DorisRating, 5 stars1 week ago
This was my first Airbnb experience and it was exceptional! The host communicated very well and was very responsive. The condo was very clean and the location was great as it was super close to great restaurants and local shops. I would definitely rent again!
Guest favourite
Apartment in Basye
4.85 out of 5 average rating, 33 reviews

Mountain View’s, pet friendly, walk to Lake Laura

StephanieRating, 5 stars5 days ago
This was exactly what my husband and I needed to get out of the busy shuffle of the cities. Peaceful. Great breweries nearby! The house was very clean, but still had that cabin feel. Porch was a great place to sit and drink coffee or hang out with beautiful views.

Apartment rentals with a pool

Superhost
Apartment in Syria
4.82 out of 5 average rating, 17 reviews

Redwood 2 Condo Graves Mountain Farm in Blue Ridge

LindaRating, 5 stars25 months ago
We wanted a quiet place away to enjoy nature. This was perfect. A few miles from great waterfall hiking…white Oak Canyon in SNP. We enjoy birding and found there was a great variety of birds to be heard. The leaves were pretty full on the trees, so viewing them was the challenge. We enjoyed the deck for birding right at the rental! We had three couples, a fourth invited but unable to come, so every couple had their own space. We prepared all our food, and the kitchen had a lot of space, and modestly stocked with utensils, etc. Being older our caloric needs were not much, so we did not feel we could eat our moneys worth at the restaurant. We really enjoyed the live music in the serene setting on Fri eve. We enjoyed watching the storm pass through Sat eve and the rainbow that formed.
Apartment in Massanutten
4.67 out of 5 average rating, 3 reviews

Summit Hillside at Massanutten

KristaRating, 5 stars19 months ago
Stayed here for a weekend getaway and loved every minute. Beautiful location, comfy beds, excellent bathtub. Make sure to spend some time sitting on the covered porch off the living room.
Apartment in Mercersburg
4.56 out of 5 average rating, 34 reviews

The Music Room at Ski Whitetail!

KendraRating, 5 stars4 months ago
This studio apartment-room was a great stay! It was the closest building to the top of the Double lift, 8-10 minutes from line to the apt door. Everything was as described for me, sans a guitar and a table or two. The wifi was fine for work, not great for gaming on my pc, though. Overall, my pet and I enjoyed every second of our 2+ weeks, on and off the slopes (just me), and look forward to staying again. Thanks!
Superhost
Apartment in Massanutten

Eagle Trace Condo at Massanutten 1br/1ba hottub

DivyaRating, 5 stars54 months ago
We had a great time at Ann’s place! She was very communicative and easy/quick to reach whenever we had a question. The place was was so comfortable and we really enjoyed relaxing in the jacuzzi after our long days on the slopes. Would definitely recommend!
Apartment in Massanutten
4.51 out of 5 average rating, 94 reviews

Massanutten Woodstone 1 Bedroom Standard Condo

AshleyRating, 5 stars3 weeks ago
Great little weekend getaway! The one bedroom Condo with partial kitchen was perfect! Tons of activities to do around the resort! We will return!
Apartment in Massanutten
4.92 out of 5 average rating, 12 reviews

Luxury 2BR 2BA w Hot Tub bath at Massanutten

AmitRating, 5 stars29 months ago
Great place and responsive host.
Superhost
Apartment in Alexandria
4.86 out of 5 average rating, 14 reviews

The Fountains condo one bedroom 2 level apartment

MaybelleRating, 5 stars4 months ago
The host was more than accommodating and the condo Is exactly as pictured . Great stay
Superhost
Apartment in Mount Jackson
4.63 out of 5 average rating, 16 reviews

Aspen East 313/314 -- SKI-IN/SKI-OUT!

DanielRating, 5 stars4 months ago
The place was dated (as noted) but also roomy and cozy. You certainly can’t beat the price and location for skiing. Solid value I’d say.

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