Extended Stay Hotels in Winchester, VA

Find 15 extended stay hotels in Winchester, VA with kitchens, free Wi-Fi, and pools. Check rates for stays near Shenandoah University and Downtown-book now for exclusive deals.

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1-15 out of 15
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  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
9.1
Perfect703 total reviews
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54 yd from City Center97 yd from Winchester Beauty School
Saltwater PoolWellness CenterFitness Center
  • Roman bathhouse-style indoor pool
  • Historic 1920s building charm
  • Full-service spa treatments
FromUS$ 109 /nightSelect
8.5
Great1257 total reviews
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4.8 mi from City Center171 yd from Alamo Drafthouse Cinema
Indoor PoolFitness CenterBusiness Center
  • Pet-friendly, two pets per room
  • Complimentary cookies and lemon water
  • Clean indoor pool praised by guests
FromUS$ 85 /nightSelect
8.7
Great1784 total reviews
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1.9 mi from City Center1073 yd from Apple Blossom Mall
Indoor PoolFitness CenterEvent Space
  • Indoor splash pool
  • Peloton bikes in fitness center
  • Pet-friendly with low fees
FromUS$ 107 /nightSelect
8.8
Great198 total reviews
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1.4 mi from City Center700 yd from Apple Blossom Mall
Heated PoolFitness CenterAmerican Restaurant
  • Executive Chef Marvin personal service
  • Pet-friendly first-floor rooms with outdoor access
  • Complimentary cookies at check-in
FromUS$ 142 /nightSelect
9.0
Perfect359 total reviews
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2.1 mi from City Center856 yd from Apple Blossom Mall
Indoor PoolFitness CenterKemp's Restaurant
  • Sit-down breakfast with menu ordering
  • Soundproof guest rooms for quiet sleep
  • Complimentary shuttle to local attractions
FromUS$ 94 /nightSelect
9.1
Perfect584 total reviews
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5.0 mi from City Center132 yd from Alamo Drafthouse Cinema
Fitness CenterBusiness CenterGolf Course
  • Near Cedar Creek National Historical Park
  • Gluten-free breakfast included daily
  • Pet-friendly policy for small dogs
FromUS$ 103 /nightSelect
9.1
Perfect213 total reviews
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1.9 mi from City Center228 yd from Sunnyside Plaza Shopping Center
Saltwater PoolHot TubFitness Center
  • Heated saltwater pool and jacuzzi
  • Free hot Express Start breakfast
  • Newly renovated fitness center
FromUS$ 136 /nightSelect
8.6
Great258 total reviews
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2.0 mi from City Center1382 yd from Rock Harbor Golf Course
Indoor PoolHot TubBistro
  • Steps from Winchester Medical Center
  • Bistro serving Starbucks coffee
  • Indoor pool and hot tub
FromUS$ 119 /nightSelect
7.0
Very good486 total reviews
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2.0 mi from City Center828 yd from Apple Blossom Mall
Indoor PoolBusiness CenterFitness Center
  • Indoor heated pool open all year
  • Personalized breakfast service
  • 12 PM checkout time
FromUS$ 80 /nightSelect
9.2
Perfect291 total reviews
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3.1 mi from City Center2.7 mi from Sunnyside Plaza Shopping Center
Heated PoolFitness CenterBusiness Center
  • Family suites with trundle beds
  • Year-round heated indoor pool
  • Gluten-free hot breakfast option
FromUS$ 133 /nightSelect
7.7
Very good158 total reviews
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2.0 mi from City Center1307 yd from Apple Blossom Mall
Fitness CenterBusiness CenterFull Kitchen
  • Full kitchen in every suite
  • On-site barbecue and picnic area
  • In-room DVD player and board games
FromUS$ 106 /nightSelect
8.9
Great221 total reviews
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1.4 mi from City Center342 yd from Lowry Tennis Courts
Saltwater PoolFitness CenterBusiness Center
  • Complimentary fresh cookies at check-in
  • Seasonal salt-water outdoor pool
  • Proximity to Shenandoah University
FromUS$ 118 /nightSelect
8.8
Great296 total reviews
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1.9 mi from City Center587 yd from Apple Blossom Mall
Indoor PoolFitness CenterBicycle Rental
  • Newly redesigned lobby and public spaces
  • Free bike rental available
  • Complimentary snacks on select nights
FromUS$ 113 /nightSelect
9.2
Perfect136 total reviews
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1.8 mi from City Center1359 yd from Jammin Gym
Bicycle RentalFitness Center24-Hour Market
  • Free bicycle rentals
  • Suites with full kitchens
  • 24-hour market for snacks
FromUS$ 126 /nightSelect
8.8
Great38 total reviews
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2.5 mi from City Center1540 yd from Apple Blossom Mall
Indoor PoolFitness CenterFull Kitchens
  • Full kitchens in every suite
  • Pet-friendly accommodations
  • Indoor pool open year-round
FromUS$ 112 /nightSelect

For travelers needing more than a single night in Winchester, extended stay hotels in the area offer practical suites with fully equipped kitchens, dedicated work areas, and reliable free Wi-Fi. These properties are concentrated near key corridors like I-81 and Shenandoah University, making them suitable for business trips, relocations, or longer family visits. The George Washington - A Wyndham Grand Hotel stands out with its spa and saltwater pool, while SpringHill Suites provides an outdoor fireplace and complimentary breakfast-both earning Superb guest scores.

Budget expectations range from $80 to $150 per night depending on the property and season. For extended stays, La Quinta By Wyndham Winchester and Comfort Inn & Suites Winchester offer free parking and fitness centers, trimming daily costs. Look for hotels in the Millwood Pike area for quick highway access, or closer to Old Town for walkable dining and historic sites. Always ask about weekly rates directly-many properties, including Sleep Inn & Suites Winchester Near University, provide discounts that aren't listed online. Book early to secure availability during peak fall foliage and university events.