Search for vacation rentals in Winchester.

Whether it's vacation home rentals, apartments, condos, or cabins/cottages, we have you covered -- search for rental properties in the entire Winchester area to find the perfect spot for your vacay.

305 N Kent St
	305 N Kent St Winchester, 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
	103 Tudor Dr Winchester, 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
	100 Muse Dr Winchester, 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
	1705 Brandon Dr Winchester, 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
	420 S Kent St Winchester, 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
	104 W Southwerk St Winchester, 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
	3782 Wardensville Grade Winchester, 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
	678 National Ave Winchester, 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
	380 Fox Run Ln Winchester, 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
	103 Pebble Brook Ln Winchester, 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
	12 E Cecil St Winchester, 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
	302 Longview Ave Winchester, 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
	102 Ridge Ct Winchester, 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
	318 Highland Ave Winchester, 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
	309 S Cameron St Winchester, 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
	179 Rossum Ln Winchester, 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
	597 Front Royal Pike Winchester, 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
	320 Fairview Ave Winchester, 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
	103 Doe Ct Winchester, 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
	346 Saddleback Ln Winchester, 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
	365 Shenandoah Ave Winchester, 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
	396 Iris Ln Winchester, 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
	311 Walker St Winchester, 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
	113 Ash Hollow Dr Winchester, 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
	1116 Allen Dr Winchester, 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
	125 Copperfield Ln Winchester, 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
	112 Thornton Way Winchester, 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
	141 Country Park Dr Winchester, 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
	321 Fairview Ave Winchester, 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
	1 Butler Ave Winchester, 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
	135 Hill Valley Dr Winchester, 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
	132 Pyramid Dr Winchester, 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
	346 Bufflick Rd Winchester, 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
	109 W Cork St Winchester, 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
	108 Cannon Cir Winchester, 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
	1306 Vanceright Cir Winchester, 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
	202 Russelcroft Rd Winchester, 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
	224 Lake Sever Dr Winchester, 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
	1001 S Cameron St Winchester, 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......

110 Hunter Run Rd
	110 Hunter Run Rd Winchester, VA $1,600 Vacation Rentals, Unknown Immaculately remodeled 2 bed 1 1/2 bath townhome NOW READY FOR OCCUPANCY! Brand new kitchen with island and stainless steel appliances, freshly painted throughout, new flooring, new bathrooms, and......