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Browse Select Gainesboro Apartments

Berryville Bliss: Basement Apartment in welcoming Berryville
Outdoor dining

Berryville Bliss: Basement Apartment in welcoming Berryville

10.0 out of 10, Exceptional, (3)
"Clean, comfortable and close to Historic Rosemont! Pool was incredible!"
The price is CA $279
CA $663 total
includes taxes & fees
Aug 11 - Aug 12
Berryville Bliss: Basement Apartment in welcoming Berryville
Cozy English Basement Apt quiet but close to downtown
Stunning two-story home with a charming front entrance and a beautiful view of the sky.

Cozy English Basement Apt quiet but close to downtown

9.6 out of 10, Exceptional, (7)
"Downtown Winchester is charming, and the property was an easy walk from downtown (though in a safe suburban neighborhood). The property itself was just as advertised. I was able to cook meals there; the bed was comfortable; it was much nicer and more varied than a hotel room."
Cozy English Basement Apt quiet but close to downtown
Nostalgia Lane in the heart of the city
Cozy retreat with a large bed, bedside tables, and artwork adorns the walls.

Nostalgia Lane in the heart of the city

8.8 out of 10, Excellent, (10)
"Great location in the heart of Winchester. Walking distance to everything. "
The price is CA $274
CA $483 total
includes taxes & fees
Aug 5 - Aug 6
Nostalgia Lane in the heart of the city
The Blue Door steps from Handley Library
Stairs lead to the entrance of this residential building, flanked by black iron railings and a small mailbox.

The Blue Door steps from Handley Library

2.0 star property
7.0 out of 10, Good, (2)
"Perfect. Met all expectations. Small but Great."
The price is CA $110
CA $211 total
includes taxes & fees
Aug 5 - Aug 6
The Blue Door steps from Handley Library
Luxe Dome w Hot Tub, King Bed, Full Bath & FirePit
Relax in a serene hot tub surrounded by a deck and tranquil surroundings.

Luxe Dome w Hot Tub, King Bed, Full Bath & FirePit

9.4 out of 10, Exceptional, (3)
"This property was really cool to stay at. Nice and cozy with everything needed for a comfortable stay. "
The price is CA $311
CA $529 total
includes taxes & fees
Aug 25 - Aug 26
Luxe Dome w Hot Tub, King Bed, Full Bath & FirePit
The Neat Nest- 1 bedroom apartment
Enjoy cooking in this well-equipped kitchen with a dishwasher, microwave, and oven.

The Neat Nest- 1 bedroom apartment

2.0 out of 10, (1)
"This was supposed to have been an anniversary stay. It was not cozy, clean or anything I expected. While the manager was easy to contact. He refused to see the problems with the property. He acknowledged knowing some of the issued and said they could have had maintenance take care of them had I elected to stay. I felt as if that should have been addressed before my stay. I tried to get a partial refund. They refused. We stayed no nights!! When I advised I was going to leave a negative review....
The Neat Nest- 1 bedroom apartment
Morocco Loft 2BR overlooking city walking mall
Relax in this inviting living space with a plush sofa, ottoman, and warm ambiance.

Morocco Loft 2BR overlooking city walking mall

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great property with all the comforts of home"
The price is CA $245
CA $436 total
includes taxes & fees
Sep 1 - Sep 2
Morocco Loft 2BR overlooking city walking mall
Luxe Dome w/ Hot Tub, Full Bath & Mountain View!
Relax in this stylish bedroom with a large bed, wall-mounted lights, and a unique tent-like ceiling.

Luxe Dome w/ Hot Tub, Full Bath & Mountain View!

10.0 out of 10, Exceptional, (4)
"Fabulous, will visit again"
The price is CA $302
CA $469 total
includes taxes & fees
Aug 12 - Aug 13
Luxe Dome w/ Hot Tub, Full Bath & Mountain View!
Charming Loft In Winchester Va, Furnished and all Inclusive
Living area

Charming Loft In Winchester Va, Furnished and all Inclusive

6.0 out of 10, (2)
"I believe we stayed at the apartment too soon after a recent fire.It was not ready for renters quite yet so our experience was not a good one."
Charming Loft In Winchester Va, Furnished and all Inclusive
The "Drop-in" Downtowner
Distinctive green door with white architectural details and large windows, offering a glimpse into the vibrant Downtown Jinedown area.

The "Drop-in" Downtowner

10.0 out of 10, Exceptional, (1)
"excellent stay! drew delivered on all aspects. will be back."
The "Drop-in" Downtowner
The Nashville Experience
Relax in a spacious bedroom with a large bed, TV, and potted plant, surrounded by a clean and minimalistic design.

The Nashville Experience

The price is CA $116
CA $256 total
includes taxes & fees
Aug 10 - Aug 11
The Nashville Experience
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Enjoy meals in this dining area with a table and benches, surrounded by a simple, clean design.

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

9.0 out of 10, Wonderful, (6)
"Lots of stairs to the bedroom and the tub shower was hard to get into for someone with knee problems. The washer dryer was off premises around to the back to the back of the house. wish they had left written instructions about how to get there , had to text her. Location was great!"
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
The Speakeasy Listening Room
Cozy retreat with a large bed, wooden beams, and a chandelier.

The Speakeasy Listening Room

10.0 out of 10, Exceptional, (1)
"Me and my girlfriend throughly enjoyed every bit of this place. Everything was set up perfectly and we had no troubles getting in. This spot is beautiful and set up very nicely We definitely plan to stay here again in the future no complaints "
The price is CA $136
CA $282 total
includes taxes & fees
Aug 10 - Aug 11
The Speakeasy Listening Room
The Soho Cooler Vibe
Welcome to a classic building with a charming entrance, featuring a covered porch and a large window offering a glimpse inside.

The Soho Cooler Vibe

The Soho Cooler Vibe
The Little Red Schoolhouse
Enjoy cooking in this well-lit kitchen with an oven, sleek stove, and stainless steel sink.

The Little Red Schoolhouse

9.8 out of 10, Exceptional, (8)
"We loved the overall school house theme. Very comfortable accommodations! "
The price is CA $121
CA $286 total
includes taxes & fees
Aug 14 - Aug 15
The Little Red Schoolhouse
Rosamond nice downtown studio apt
Relax in this serene space with a dining table for two, a bookshelf filled with personal treasures, and a large window for a peaceful view.

Rosamond nice downtown studio apt

8.0 out of 10, Very good, (2)
"Small but appropriately priced."
The price is CA $152
CA $266 total
includes taxes & fees
Aug 5 - Aug 6
Rosamond nice downtown studio apt
Charming 1-bedroom apartment with AC, WiFi in pleasant Winchester pet-friendly
Relax in this stylish living space with a tufted sofa, wooden coffee table, and abstract art on the walls.

Charming 1-bedroom apartment with AC, WiFi in pleasant Winchester pet-friendly

2.0 out of 10, (1)
"For a new listing to VRBO, the property did not meet our expectations. Check in time on app was incorrect delaying our activities. Communication with owner was delay and resulted in conversation with VRBO. Pictures of apartment were not accurate to the unit. The property is in a "Corporate Apartment" complex but apartment is nowhere near the standards of a corporate apartment. The cable remote didn't work. TV in bedroom was plugged in but no cable hook up. Windowsill and door frame damaged by...
Charming 1-bedroom apartment with AC, WiFi in pleasant Winchester pet-friendly
Cameron Grace Brand New 1BR 1BA apt downtown Winchester
Enjoy cooking in this well-equipped kitchen with a gas stove, oven, and granite countertop.

Cameron Grace Brand New 1BR 1BA apt downtown Winchester

2.0 star property
10.0 out of 10, Exceptional, (4)
"The apartment is beautiful, comfortable and private. We enjoyed our quick getaway to Winchester."
Cameron Grace Brand New 1BR 1BA apt downtown Winchester
Luxe 2 Bed Dome w Hot Tub, Deck, Fire Pit & Bath
Relax in a spacious bedroom with a large bed, nightstands, and a sofa, surrounded by abstract artworks and a wooden ladder.

Luxe 2 Bed Dome w Hot Tub, Deck, Fire Pit & Bath

1.0 star property
6.0 out of 10, (2)
"When we arrived we were a little disappointed in how close the neighboring places were but it turned out not to be a problem. There are lots of trees but they didn’t have very many leaves so no shade. Small refrigerator but other than that we enjoyed it. It was a very unique place, it felt like you were sleeping outside."
The price is CA $223
CA $386 total
includes taxes & fees
Aug 13 - Aug 14
Luxe 2 Bed Dome w Hot Tub, Deck, Fire Pit & Bath
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Enjoy cooking in this fully equipped kitchen with a stove, kettle, coffee maker, and sink.

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

2.0 star property
8.0 out of 10, Very good, (3)
"Clean property. Convenient to Old Town Winchester. All and all good property. Needs new bedroom pillows. Best."
The price is CA $190
CA $320 total
includes taxes & fees
Aug 5 - Aug 6
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Gainesboro Hotel Reviews

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"Friendly staff. Good location. Lots of places to eat. Within walking distance. Property was clean. And well maintained. "
Frank 1-night trip
Posted 1 day ago
Comfort Inn & Suites Winchester