Luxury Cruises - Vacation Rentals in Winchester

Luxury Places to Stay in Winchester

Over 77+ Luxury Places to Stay in or Near Winchester
Cozy Up and Get Comfortable From US $869
         

10.0 (7 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
Tip Of The Town Fresh and New 3 Bedroom Nest From US $350
         

10.0 (26 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Thunder Hill Retreat - Spacious/Deck/Hot tub From US $350
         

10.0 (16 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Balcony/Terrace
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 $115
         

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 $98
         

8.6 (758 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 (537 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Express Hotel & Suites-North East by IHG From US $188
         

Pet-Friendly Vacation Rentals in Winchester

Over 17+ Pet-Friendly Vacation Rentals in or Near Winchester
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 $106
         

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9.0 (1003 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio From US $196
         

9.8 (44 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Summer Rustic Camping with AC and King Bed From US $158
         

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

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 $112
         

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9.0 (541 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 $98
         

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 25+ Winchester Varoom and Airbnb Places to Stay Under $200
Cozy 1-bedroom apartment with WiFi, AC in enjoyable Newark From US $126
         

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 (183 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Cozy Cottage on the North East River in Town! From US $191
         

10.0 (2 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Fair Hill Cabin-10 mins to Newark/UD From US $168
         

9.8 (10 Reviews)
Cabin
  • 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
Room #4 in Elkton, MD – Easy Access to I-95 From US $126
         

New
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Instantly Bookable Vacation Homes in Winchester

Over 15+ Instantly Bookable Vacation Homes in or Near Winchester
Modern cozy get-away* game room-amish country From US $290
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
apartment in Elkton Maryland From US $211
         

6.8 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
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
         

Lovely 2 bedroom unit with free parking in front. No steps From US $81
         

4.9 (9 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace

About Winchester Vacation Rentals

With more than 77 Winchester vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Luxurycruises 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 Luxurycruises 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

Luxurycruises 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.

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