Sonoma Villas - Vacation Rentals in Winchester

Lakeview home 6 mins drive to University of Delaware From US $342
         

Luxury Places to Stay in Winchester

Over 77+ Luxury Places to Stay in or Near Winchester
Luxury Retreat Meets Maximum Comfort From US $909
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Rustic Chic Cabin In Southern Chester County PA From US $473
         

9.8 (81 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Thunder Hill Retreat - Spacious/Deck/Hot tub From US $446
         

10.0 (17 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Spacious 4-bedroom house with AC in Elkton.
New
From US $324
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • TV

Top-Rated Vacation Rentals with a Pool in Winchester

Over 9+ Top-Rated Vacation Rentals with a Pool in or Near Winchester
Holiday Inn Express & Suites Elkton - University Area by IHG From US $110
         

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

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8.8 (221 Reviews)
Hotel
  • Air Conditioner
  • Pool
  • Wheelchair Accessible
Hampton Inn Elkton From US $93
         

8.6 (790 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
La Quinta by Wyndham Newark - Elkton From US $138
         

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8.6 (506 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Courtyard by Marriott Newark-University of Delaware From US $189
         

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8.6 (66 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Holiday Inn Express North East by IHG From US $100
         

8.4 (548 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express Hotel & Suites-North East by IHG From US $188
         

Comfort Inn & Suites North East From US $89
         

7.8 (653 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Winchester

Over 16+ Pet-Friendly Vacation Rentals in or Near Winchester
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio From US $196
         

9.8 (45 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Sutton Inn From US $169
         

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8.9 (153 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
La Quinta Inn & Suites by Wyndham Newark - Elkton From US $108
         

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9.0 (1002 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Summer Rustic Camping with AC and King Bed From US $153
         

9.6 (5 Reviews)
House
  • Pet Friendly
  • Balcony/Terrace
  • Security/Safety
2bed 2bath first floor unit with deck
New
From US $97
         

New
Condo
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Lovely 2 bedroom unit with free parking in front From US $123
         

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

Large Vacation Homes & Villas in Winchester

Over 3+ 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
Elk Forge Bed and Breakfast From US $129
         

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8.0 (88 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • View
Villa with hot tub on Ash Lane From US $423
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Winchester

Over 7+ Wheelchair Accessible Vacation Homes in or Near Winchester
Elkton Lodge - Newark - Elkton University Gateway From US $89
         

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9.1 (8 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • View
Courtyard by Marriott Newark-University of Delaware From US $129
         

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9.0 (546 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Wingate by Wyndham North East From US $109
         

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8.3 (121 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Homewood Suites by Hilton Newark-Wilmington South Area From US $85
         

Hampton Inn Elkton From US $172
         

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7.9 (113 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Motel 6-Elkton, MD From US $70
         

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5.8 (195 Reviews)
Hotel
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
Travelodge by Wyndham Elkton University Area From US $63
         

5.1 (89 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • Wheelchair Accessible

Winchester Varoom and Airbnb Places to Stay Under $200

Over 24+ Winchester Varoom and Airbnb Places to Stay Under $200
Fair Hill Cabin-10 mins to Newark/UD From US $147
         

10.0 (12 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Comfort Inn & Suites North East From US $107
         

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7.6 (207 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Elk Forge B&B Inn & Day Spa From US $137
         

8.8 (185 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Cozy 1-bedroom apartment with WiFi, AC in enjoyable Newark From US $125
         

Cozy Cottage on the North East River in Town! From US $192
         

10.0 (2 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
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 15+ Instantly Bookable Vacation Homes in or Near Winchester
Tip Of The Town Fresh and New 3 Bedroom Nest From US $288
         

10.0 (26 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Modern cozy get-away* game room-amish country From US $290
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Room #2 in Elkton, MD – Easy Access to I-95 From US $104
         

New
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Charming riverside home From US $219
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
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
Cozy home near UD Campus and Main Street. Quiet neighborhood, has a fireplace! From US $180
         

About Winchester Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Sonomavillas 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 2572.57 ft² on average, with prices averaging $342 a night.

Sonomavillas 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
Villas 1

Use these Quick Filters to Find a Vacation Rental in Winchester

Pro Tip: Sonomavillas makes it easy to compare the best listings on Sonomavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Sonomavillas 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