Villas Mykonos - Vacation Rentals in Winchester

Tip Of The Town Fresh and New 3 Bedroom Nest From US $411
         

10.0 (27 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Elk Forge Bed and Breakfast From US $149
         

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8.4 (54 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Elk Forge B&B Inn & Day Spa From US $137
         

8.8 (200 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Thunder Hill Retreat - Spacious/Deck/Hot tub From US $468
         

10.0 (20 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Modern cozy get-away* game room-amish country From US $432
         

10.0 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Spring has Sprung, Visit Woodland Retreat Today! From US $1,164
         

10.0 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy 1-bedroom apartment with WiFi, AC in enjoyable Newark From US $136
         

Luxury Places to Stay in Winchester

Over 75+ Luxury Places to Stay in or Near Winchester
Lux Family Retreat, Sauna, Hot Tub Games, Swingset From US $1,388
         

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New
House
  • Security/Safety
  • Wellness Facilities
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Kid-Friendly Near UD, 1st-Floor Master + Office From US $825
         

The Modern Getaway, Amish Country, Game Room From US $645
         

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New
House
  • View
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Secluded Log Cabin Escape on Private Pond & Acres From US $527
         

9.8 (81 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Your Home Away from Home: The Waverly From US $517
         

New
Apartment
  • Air Conditioner
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  • Pet Friendly
Lakeview home 6 mins drive to University of Delaware From US $342
         

Top-Rated Vacation Rentals with a Pool in Winchester

Over 10+ Top-Rated Vacation Rentals with a Pool in or Near Winchester
Holiday Inn Express & Suites Elkton - University Area by IHG From US $134
         

Holiday Inn Express & Suites Elkton - University Area by IHG From US $167
         

Hampton Inn Elkton From US $114
         

8.6 (849 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
La Quinta by Wyndham Newark - Elkton From US $204
         

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8.6 (443 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Holiday Inn Express Hotel & Suites-North East by IHG From US $191
         

Holiday Inn Express North East by IHG From US $137
         

8.4 (576 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hampton Inn Elkton From US $172
         

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8.1 (111 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Winchester

Over 19+ Pet-Friendly Vacation Rentals in or Near Winchester
Summer Rustic Camping with AC and King Bed From US $163
         

9.8 (6 Reviews)
House
  • Pet Friendly
  • Balcony/Terrace
  • Security/Safety
Sutton Inn From US $149
         

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8.9 (149 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
La Quinta Inn & Suites by Wyndham Newark - Elkton From US $129
         

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9.0 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio From US $206
         

9.6 (50 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Lovely 2 bedroom unit with free parking in front From US $139
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Charming 3-bedroom house with WiFi, AC in Newark DE, walking distance to UDEL From US $459
         

Large Vacation Homes & Villas in Winchester

Over 2+ Large Vacation Homes & Villas in or Near Winchester
Villa with hot tub on Ash Lane From US $443
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Villa with hot tub on Ash Lane From US $423
         

New
House
  • Air Conditioner
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  • Pet Friendly

Wheelchair Accessible Vacation Homes in Winchester

Over 6+ Wheelchair Accessible Vacation Homes in or Near Winchester
Elkton Lodge - Newark - Elkton University Gateway From US $131
         

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8.8 (29 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Courtyard by Marriott Newark-University of Delaware From US $131
         

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9.0 (569 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Wingate by Wyndham North East From US $109
         

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8.4 (150 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Homewood Suites by Hilton Newark-Wilmington South Area From US $108
         

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8.0 (963 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Motel 6-Elkton, MD From US $97
         

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6.0 (177 Reviews)
Hotel
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
Travelodge by Wyndham Elkton University Area From US $63
         

4.7 (89 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • Wheelchair Accessible

Winchester Vacation Rentals and Airbnb Places to Stay Under $200

Over 26+ Winchester Vacation Rentals and Airbnb Places to Stay Under $200
Comfort Inn & Suites North East From US $148
         

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7.7 (241 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Elkton Lodge - Newark - Elkton - University Gateway From US $132
         

8.6 (37 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Inviting, comfortable & private suite near Univ. From US $116
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Fair Hill Cabin-10 mins to Newark/UD From US $147
         

10.0 (12 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Cozy home near UD Campus and Main Street. Quiet neighborhood, has a fireplace! From US $180
         

apartment in Elkton Maryland From US $157
         

6.8 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Room #3 in Elkton, MD – Easy Access to I-95 From US $125
         

5.0 (2 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Instantly Bookable Vacation Homes in Winchester

Over 13+ Instantly Bookable Vacation Homes in or Near Winchester
Sweet Little Home Away From Home, North East, MD From US $327
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety
Modern and Spacious townhome minutes from UDel From US $398
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Sweet Little Home Away From Home From US $525
         

New
House
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  • Parking
  • Balcony/Terrace
Charming 3rd floor Large bedroom inside townhome From US $341
         

About Winchester Vacation Rentals

With more than 84 Winchester vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Villas Mykonos and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Winchester.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Villas Mykonos Winchester, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Winchester. Places to stay near Winchester are 1597.05 ft² on average, with prices averaging US $260 a night.

Villas Mykonos makes it easy and safe to find and compare vacation rentals in Winchester with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Winchester

Type Count
Vacation Homes 37
Hotels 27
Holiday Apartments 11
B&B 2
Cabin Rentals 2
Cottages 2
Others 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Winchester

Pro Tip: Villas Mykonos makes it easy to compare the best listings on Villas Mykonos homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Villas Mykonos homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Winchester.

Weather in Winchester

View the weather forecast for Winchester before booking your Winchester Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Winchester Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Winchester?
How many vacation rentals are available in Winchester?

Currently, the total number of properties listed in 2026 is over 84 in the Winchester area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Winchester.