Here are Winchester listings for rentals and roommates -- find yourself a whole new living arrangement by choosing from apartments, homes for rent, and other rooms for rent.
Also, if you're only passing through Winchester for a brief period of time, find short term rentals or vacation rentals.
105 Green Park Dr |
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105 Green Park DrWinchester, VA$1,595
Vacation Rentals, Unknown
3 bedroom, 1 bathroom ranch-style house. Recently replaced kitchen cabinets, countertops, and appliances. Recently replaced windows & doors. New carpet. Fenced-in backyard with storage shed. Washer...... |
305 N Kent St |
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305 N Kent StWinchester, VA$2,300
Vacation Rentals, Unknown
Fully renovated home just a few houses away from the historic downtown walking mall with much desired off street parking. This fully detached house has a complete kitchen with eat in dining room...... |
103 Tudor Dr |
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103 Tudor DrWinchester, VA$1,700
Vacation Rentals, Unknown
This 3 level townhome has 2 bedrooms & 3 1/2 full baths. Located in a convenient location and offering a fireplace in the living room.... |
100 Muse Dr |
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100 Muse DrWinchester, VA$1,795
Vacation Rentals, Unknown
Updated Pictures Coming Make this charming rancher three bedroom your new place to call home! The list of upgrades will take your breathe away! All new floors, hardwood floors sanded and re-stained...... |
1705 Brandon Dr |
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1705 Brandon DrWinchester, VA$1,850
Vacation Rentals, Unknown
Discover the allure of this 3-bed, 2-bath oasis boasting sleek finishes, an attached garage, and a spacious driveway. Indulge your inner chef in the gourmet kitchen, then unwind in the serene...... |
420 S Kent St |
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420 S Kent StWinchester, VA$1,300
Vacation Rentals, Unknown
Coming Soon This one is for all the Rustic Charm lovers! Freshly updated 3 Bedroom 1.5 Bath Off street parking Fenced backyard Washer and dryer hookups Pet friendly Oil heat 3 Bedroom 1.5 Bath... |
104 W Southwerk St |
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104 W Southwerk StWinchester, VA$1,095
Vacation Rentals, Unknown
2 Bedroom 1 Bath Washer and dryer hookups Oil and electric heat Hardwood floors Pet friendly 2 Bedroom 1 Bath... |
3782 Wardensville Grade |
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3782 Wardensville GradeWinchester, VA$3,300
Vacation Rentals, Unknown
Very large ranch-style house with a full basement. Up to 6 different rooms for bedrooms and 4 full bathrooms. Main floor contains 5 bedrooms and 3 full bathrooms. Basement contains 1 bedroom and 1...... |
678 National Ave |
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678 National AveWinchester, VA$2,879
Vacation Rentals, Unknown
Charming 99 year old colonial recently renovated with refinished floors, newer SS appliances, counters, island, windows, and energy efficient heat pump mini-splits with independent heat/air...... |
380 Fox Run Ln |
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380 Fox Run LnWinchester, VA$2,000
Vacation Rentals, Unknown
Charming 3 bedroom 2 bathroom one-level home, with cabin style appeal, beautifully remodeled to include a large master suite, hardwood floors throughout, central heat/air, and modern kitchen. The...... |
103 Pebble Brook Ln |
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103 Pebble Brook LnWinchester, VA$2,300
Vacation Rentals, Unknown
Everything has been remodeled and it is move-in ready for you! This 3 bedroom/2.5 bath single family home in great commuting location with easy and fast access to route 7 and 81 is now available...... |
12 E Cecil St |
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12 E Cecil StWinchester, VA$2,750
Vacation Rentals, Unknown
4 Bedroom completely remodeled new everything. Heat pumps. Outbuilding. Basement. Walk up partially finished attic. Walk to old town restaurants and shopping.... |
302 Longview Ave |
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302 Longview AveWinchester, VA$3,000
Vacation Rentals, Unknown
Brand new Ryan Homes model house in Wea Villa NOW FOR RENT! This specular home features 4 bedrooms 2 1/2 baths, full unfinished walk out basement, Stainless steal appliances, washer/dryer in second...... |
102 Ridge Ct |
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102 Ridge CtWinchester, VA$1,950
Vacation Rentals, Unknown
Bright & Spacious 2 Bedroom 2.5 Bath Town House With 1 Car Garage. Fresh Paint, New Carpets Throughout The Property. Eat In Kitchen With Corian Counters Opens To New Trex Deck. Bright And Cozy...... |
318 Highland Ave |
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318 Highland AveWinchester, VA$1,900
Vacation Rentals, Unknown
Recently Renovated large Single family home in historic area* Spacious Upgraded Kitchen w/Granite counter tops, Stainless Steel appliances with Dining room off kitchen* Inviting front porch*...... |
309 S Cameron St |
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309 S Cameron StWinchester, VA$1,800
Vacation Rentals, Unknown
Large duplex just a couple of blocks off the Old Town walking mall! This two bedroom, one bath home has been freshly painted inside, with thoughtful additions like coat and shoe storage at the...... |
179 Rossum Ln |
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179 Rossum LnWinchester, VA$2,999
Vacation Rentals, Unknown
FOR RENT**BRAND NEW NEVER LIVED Single Family ** DESCRIPTION: THIS TO HOUSE HAS 2 LEVELS, A 2-CAR GARAGE, AND AN OPEN FLOOR PLAN. 2064 FINISHED SQUARE FEET!! THE MAIN LEVELS WILL HAVE LUXURY VINYL...... |
597 Front Royal Pike |
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597 Front Royal PikeWinchester, VA$2,500
Vacation Rentals, Unknown
OPEN HOUSE, OPEN HOUSE, OPEN HOUSE March 9th, 11am - 2pm Exquisitely Renovated 4-Bedroom Home with Modern Amenities and Outdoor Retreat Relax in this beautiful fully renovated 4-bedroom home,...... |
320 Fairview Ave |
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320 Fairview AveWinchester, VA$1,700
Vacation Rentals, Unknown
3 BEDROOM, 1 BATH HOME LOCATED VERY CLOSE TO ROUTE 7, I-81 AND DOWNTOWN and minutes from the park and shopping!! Cute colonial home with big fenced in backyard for kids and/or pets. Wood floors,...... |
103 Doe Ct |
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103 Doe CtWinchester, VA$1,200
Vacation Rentals, Unknown
This home is a part of the Wilde Acres/Mountain Falls community and is owned by the Wilde Acres Property Owner's Association (WAPOA). The location of the home is at the front of the community,...... |
346 Saddleback Ln |
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346 Saddleback LnWinchester, VA$2,495
Vacation Rentals, Unknown
Colonial on 5 acres. Beautiful layout features 4 generous bedrooms, 2.5 baths, roomy eat-in kitchen with breakfast counter, living room with brick fireplace, sunny formal dining room with bay...... |
365 Shenandoah Ave |
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365 Shenandoah AveWinchester, VA$2,900
Vacation Rentals, Unknown
Enjoy this completely renovated home! 5 bedrooms, 3 full baths! Open and contemporary full of light! Main level features gourmet kitchen with new cabinets & quartz counters. All new stainless...... |
396 Iris Ln |
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396 Iris LnWinchester, VA$1,295
Vacation Rentals, Unknown
2 Bedroom 1 Bath Beautiful wooded lot. Frederick County residence. Well & septic Large front porch. Newly painted exterior and interior. 2 Bedroom 1 Bath... |
311 Walker St |
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311 Walker StWinchester, VA$2,700
Vacation Rentals, Unknown
Beautifully remodeled home in quiet neighborhood close to hospital and downtown. Upgrades include granite counters, custom tile, and hardwood floors. Main floor features open concept kitchen with...... |
113 Ash Hollow Dr |
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113 Ash Hollow DrWinchester, VA$1,650
Vacation Rentals, Unknown
Open and bright 3 bedroom 1 1/2 bath townhome now available for rent. Freshly painted and new flooring throughout with brand new stainless steel appliances. Animals considered on a case by case basis.... |
1116 Allen Dr |
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1116 Allen DrWinchester, VA$1,200
Vacation Rentals, Unknown
Welcome to the epitome of convenience at 1116 Allen Dr.! If you're searching for a place that offers proximity to everything, look no further. This apartment is just minutes away from Rt. 7 and 81,...... |
125 Copperfield Ln |
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125 Copperfield LnWinchester, VA$1,650
Vacation Rentals, Unknown
3 bedroom 1 1/2 bath townhome in Copperfield Townhome community. Water/sewer included in the rent. Pets considered case by case basis. Fenced rear yard and storage building.... |
112 Thornton Way |
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112 Thornton WayWinchester, VA$2,500
Vacation Rentals, Unknown
Brand New House available for rent. This is a one floor, ranch style home with no stairs. Wide Open Spaces. Situated off the foyer is a bedroom, bathroom, laundry room, home office or third...... |
141 Country Park Dr |
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141 Country Park DrWinchester, VA$1,595
Vacation Rentals, Unknown
Newly remodeled 3 bedroom, 1 bathroom ranch house. New kitchen cabinets, new granite countertops, and new stainless steel appliances. New flooring throughout. New bathroom fixtures. New light...... |
321 Fairview Ave |
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321 Fairview AveWinchester, VA$1,900
Vacation Rentals, Unknown
Fully renovated home in a great location! This adorable historic charmer is totally ready for you. Completely renovated from top to bottom, with lots of special touches. The large covered front...... |
1 Butler Ave |
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1 Butler AveWinchester, VA$2,000
Vacation Rentals, Unknown
HOME DOES NOT HAVE BASEMENT HOME AVAILABLE UNTIL May 15, 2024 1.5 Bathrooms 3 bedrooms Ranch style home, one floor with a large fenced backyard. Beautiful home looking for the next tenant tha would...... |
135 Hill Valley Dr |
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135 Hill Valley DrWinchester, VA$2,291
Vacation Rentals, Unknown
This beautiful raised rancher with Front Porch and Fenced is MOVE IN READY Boast 3 bedrooms, with another potential 4th bedroom downstairs as well. High vaulted ceilings, beautiful white cabinetry,...... |
132 Pyramid Dr |
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132 Pyramid DrWinchester, VA$1,500
Vacation Rentals, Unknown
This is a trailer for rent in the Regency Lakes community. It has a brand new HVAC system, fresh paint and updated bathroom. It has 2 bedrooms and 1 full bath with a smaller room that can serve as...... |
346 Bufflick Rd |
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346 Bufflick RdWinchester, VA$2,500
Vacation Rentals, Unknown
Newly renovated property. Stainless steal appliances, granite countertops. A spa like bathroom with a huge walk in closet. A must see. A pilots dream. Sit on the balcony drinking coffee as the...... |
109 W Cork St |
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109 W Cork StWinchester, VA$1,850
Vacation Rentals, Unknown
This 1250 square foot single family home has 2 bedrooms, 1.5 bathrooms and sun room. Excellence downtown location within walking distance shops, restaurants, and many other businesses. Brick house...... |
108 Cannon Cir |
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108 Cannon CirWinchester, VA$2,900
Vacation Rentals, Unknown
Lovely 4 BR 3.5 BA SFH with 2 car attached garage, fenced yard, on quiet cul-de-sac. Master on main floor with walk in closet. Finished walk out basement with full bath. Top floor with bonus room,...... |
1306 Vanceright Cir |
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1306 Vanceright CirWinchester, VA$2,400
Vacation Rentals, Unknown
Available March 2, 2024 Charming cape cod close to Handley High School on a quiet cul de sac in a family-oriented neighborhood in town! Four bedrooms, two full baths, and over 2,200 sq feet....... |
202 Russelcroft Rd |
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202 Russelcroft RdWinchester, VA$2,200
Vacation Rentals, Unknown
Near shopping, restaurants, and Frederick Douglass elementary school, this beautiful well-maintained brick ranch home is in a well established neighborhood. This is single-level living has new...... |
224 Lake Sever Dr |
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224 Lake Sever DrWinchester, VA$1,895
Vacation Rentals, Unknown
This Split Foyer has been completely renovated. All new flooring ,finishes and freshly painted throughout. Located on cul-de-sac. Great commuter location, easy access to Route 7. Home features 4...... |
1001 S Cameron St |
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1001 S Cameron StWinchester, VA$1,595
Vacation Rentals, Unknown
**COMING SOON** Built in 1930. 3 Bedroom - 1 Bath Duplex. Convenient in-town location. Close to Valley Ave, Pleasant Valley Rd., Rt.522 S. and I-81. Refrigerator / Stove. Re-finished Hardwood...... |