Winchester

Winchester Homestays

Enter your dates to find homestays in Winchester for a cozy, local feel.

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Popular Homestays in Winchester

Check out the best homestays in Winchester for a home-like stay.
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Cozy English Basement Apt quiet but close to downtown
Cozy English Basement Apt quiet but close to downtownCozy English Basement Apt quiet but close to downtownCozy English Basement Apt quiet but close to downtownCozy English Basement Apt quiet but close to downtownCozy English Basement Apt quiet but close to downtownCozy English Basement Apt quiet but close to downtown
15
Hotels in Winchester
Your Cozy English basement studio apt is 4 blocks to the walking mall and other great downtown attractions. Ivy covered stone steps line the climb to your small home away from home. Perfect for a single or couple in need of a convenient place to stay in the town of Winchester. Close to the hospital/ shopping. D. C- 1.5 hr. Baltimore -1.5 hr. Skyline Drive 30 min Looking for more space? I have two larger houses in downtown Winchester. Find me: Michele Bouve Hoffman on social media. Happy Travels!The spaceThis basement apt has a living room with TV and DVD player, the bedroom is separated from the living area by glass french doors. Down the hall, you will find your own washer/dryer and a modest but cute kitchen(with everything one needs for cooking but no stove- but electric surface hot pads(2) )toaster oven and microwave. Then a full bath with shower. Outside your private entrance there is plenty of on street parking. The apt is not dark as there are small windows and good lighting. There are approx. 6 steps once inside to reach the apt. Like a typical basement, ceilings are not that high, so if you are over 6 feet tall -you may feel like you are in a Hobit house!Overall charming feel and also has a cozy gas fireplace. Great little spot !About pets:Pets allowed: dogs and cats (limit 1 total).About checkOut:Check out before 12:00 PM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.
Amazing
4 reviews
9.4/10
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WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
WonderClock House downtown vintage duplex w/ porches, steps to Handley LibraryWonderClock House downtown vintage duplex w/ porches, steps to Handley LibraryWonderClock House downtown vintage duplex w/ porches, steps to Handley LibraryWonderClock House downtown vintage duplex w/ porches, steps to Handley LibraryWonderClock House downtown vintage duplex w/ porches, steps to Handley LibraryWonderClock House downtown vintage duplex w/ porches, steps to Handley Library
19
Very Good
4 reviews
8.6/10
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Morocco Loft 2BR overlooking city walking mall
Morocco Loft 2BR overlooking city walking mallMorocco Loft 2BR overlooking city walking mallMorocco Loft 2BR overlooking city walking mallMorocco Loft 2BR overlooking city walking mallMorocco Loft 2BR overlooking city walking mallMorocco Loft 2BR overlooking city walking mall
9
Hotels in Winchester
Welcome to Morocco Loft ~ this is a large loft on the third floor of a vintage tudor style building high up overlooking the downtown cityscape with lots of character and charm. You will love the trendy decor and unique layout just steps from the downtown walking mall, discovery museum and the many unique shops and restaurants of Winchester.About pets:No pets allowed.About children:Children allowed: ages 0-17.About smoking:Smoking is not permitted.About events:No events allowed.
Outstanding
2 reviews
10.0/10
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Winchester
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Yellow Submarine trendy basement apt and courtyard
Yellow Submarine trendy basement apt and courtyardYellow Submarine trendy basement apt and courtyardYellow Submarine trendy basement apt and courtyardYellow Submarine trendy basement apt and courtyardYellow Submarine trendy basement apt and courtyardYellow Submarine trendy basement apt and courtyard
21
Hotels in Winchester
Featured facilities: Clothes Dryer
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The Stock Exchange downtown 3rd floor studio apt
The Stock Exchange downtown 3rd floor studio aptThe Stock Exchange downtown 3rd floor studio aptThe Stock Exchange downtown 3rd floor studio aptThe Stock Exchange downtown 3rd floor studio aptThe Stock Exchange downtown 3rd floor studio aptThe Stock Exchange downtown 3rd floor studio apt
8
Hotels in Winchester
Featured facilities: Kitchen, Washing Machine
6.0/10
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Rosamond nice downtown studio apt
Rosamond nice downtown studio aptRosamond nice downtown studio aptRosamond nice downtown studio aptRosamond nice downtown studio aptRosamond nice downtown studio aptRosamond nice downtown studio apt
10
Hotels in Winchester
Featured facilities: Kitchen
Very Good
2 reviews
8.0/10
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Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mallDreamweaver — 1BR 1BA just two blocks from the downtown walking mallDreamweaver — 1BR 1BA just two blocks from the downtown walking mallDreamweaver — 1BR 1BA just two blocks from the downtown walking mallDreamweaver — 1BR 1BA just two blocks from the downtown walking mallDreamweaver — 1BR 1BA just two blocks from the downtown walking mall
14
Hotels in Winchester
Featured facilities: Clothes Dryer
Very Good
2 reviews
8.0/10
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Lofts for weekly rentals! 2 miles from historic downtown.
Lofts for weekly rentals! 2 miles from historic downtown.Lofts for weekly rentals! 2 miles from historic downtown.Lofts for weekly rentals! 2 miles from historic downtown.Lofts for weekly rentals! 2 miles from historic downtown.Lofts for weekly rentals! 2 miles from historic downtown.Lofts for weekly rentals! 2 miles from historic downtown.
8
Hotels in Winchester
Individual loft apartments with front patios. Walk in to a living area and connected kitchenette with refrigerator. We supply dishware, silverware, toaster, coffee maker and pots and pans to use on the 2 burner stove top. Large shower and loft bedroom with a second TV. A home away from home.About pets:Pets allowed: dogs and cats less than 50 lbs per pet (limit one pet total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 17.About events:No events allowed.
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New Charming 3-Bedroom  2 Full Bath and 1 Half Bedrooms Single Family  House
New Charming 3-Bedroom  2 Full Bath and 1 Half Bedrooms Single Family  HouseNew Charming 3-Bedroom  2 Full Bath and 1 Half Bedrooms Single Family  HouseNew Charming 3-Bedroom  2 Full Bath and 1 Half Bedrooms Single Family  HouseNew Charming 3-Bedroom  2 Full Bath and 1 Half Bedrooms Single Family  House
7
Hotels in Winchester
Featured facilities: Kitchen, Washing Machine
Very Good
5 reviews
8.0/10
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Scarborough Fair walk to downtown two story apt
Scarborough Fair walk to downtown two story aptScarborough Fair walk to downtown two story aptScarborough Fair walk to downtown two story aptScarborough Fair walk to downtown two story aptScarborough Fair walk to downtown two story aptScarborough Fair walk to downtown two story apt
12
Hotels in Winchester
Come to downtown Winchester get the true feel of the city. Walk to beautiful Handley Library, take a stroll to the walking mall to the many shops & restaurants. Scarborough Fair is the place to enjoy the time w/family and friends. Three large bedrooms, two levels, three porches, and a completely fenced rear yard. Scarborough Fair is eclectic & comfortable you will love your stay in this wonderful spot downtown. Looking for more space? I have several spots in downtown Winchester. Find me: Michele Bouve Hoffman on social media. Happy Travels!The spaceThere is a living room with sofa bed and comfortable seating for 6-8 that opens into a dining area with mid century table to gather around, desk work space and fold out futon for additional guests. The modern kitchen is fully equipped with all the amenities you will need for your stay including large pantry with washer and dryer. Up the staircase to second floor is the full bath with tub and three spacious bedrooms: back bedroom has bunk bed ( twin over full) , and 2nd flat screen tv ( ROKU) middle bedroom has queen bed and is a walk thru (each bedroom has own door for privacy). Front bedroom has a queen bed and sitting area.The upper, rear and front porches are great for relaxing. Enjoy the porch rocker and listen to the sounds of the church bells ring, walk across the street and grab a book from the library or order a delicious coffee or chai tea from the Expresso Bar on the walking mall. You will love this spot ! See listing photos for wifi info. PLEASE NOTE: All major holidays ( Local: Apple Blossom National: Christmas/ Thanksgiving/ New years/4th of July /Memorial and Labor Day ) will include an additional $100 fee. This fee will be requested prior to guests arrival.Please NOTE: Stays over 3 weeks will incur an additional double cleaning fee.Quiet Hours: 10pm to 7am.About pets:Pets allowed: dogs (limit 2 total).About checkOut:Check out before 12:00 PM.About children:Children allowed: ages 0-17.The property has not been child proofed.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.
Amazing
4 reviews
9.4/10
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See all Homestays in Winchester

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