Vacation Home Lettings - Vacation Rentals in Winchester

Property Image From $312
         

9.0 (4 Reviews)
House
  • Parking
  • Internet
Property Image From $177
         

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10.0 (172 Reviews)
Bed & Breakfast
  • Parking
  • Balcony/Terrace
  • Bedding/Linens
Property Image From $180
         

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8.8 (53 Reviews)
Apartment
  • Child Friendly
  • Internet
Property Image From $335
         

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10.0 (3 Reviews)
Cottage
  • Parking
  • Balcony/Terrace
  • Security/Safety
Property Image From $154
         

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8.9 (215 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Property Image From $160
         

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10.0 (3 Reviews)
Bed & Breakfast
  • Parking
  • TV
  • Balcony/Terrace
Property Image From $381
         

New
Villa
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  • Pet Friendly
  • Balcony/Terrace
Property Image From $124
         

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10.0 (2 Reviews)
Apartment
  • Parking
  • View
  • Security/Safety

Luxury Places to Stay in Winchester

Over 146+ Luxury Places to Stay in or Near Winchester
Property Image From $923
         

9.3 (251 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $780
         

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7.8 (633 Reviews)
Bed & Breakfast
  • Parking
  • Pet Friendly
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Property Image From $741
         

New
Cottage
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Property Image From $635
         

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New
Cottage
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  • Pet Friendly
  • Balcony/Terrace
Property Image From $612
         

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8.8 (257 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • View

Top-Rated Vacation Rentals with a Pool in Winchester

Over 4+ Top-Rated Vacation Rentals with a Pool in or Near Winchester
Property Image From $449
         

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8.4 (1022 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Property Image From $171
         

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8.2 (2367 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $90
         

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6.9 (3138 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • Pool
Property Image From $192
         

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New
House
  • Parking
  • Pet Friendly
  • Pool

Pet-Friendly Vacation Rentals in Winchester

Over 32+ Pet-Friendly Vacation Rentals in or Near Winchester
Property Image From $185
         

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10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • View
Property Image From $210
         

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10.0 (1 Review)
Cottage
  • Parking
  • Pet Friendly
  • TV
Property Image From $422
         

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9.3 (6 Reviews)
House
  • Parking
  • Pet Friendly
  • View
Property Image From $239
         

9.3 (4 Reviews)
Apartment
  • Pet Friendly
  • Balcony/Terrace
  • Security/Safety
Property Image From $180
         

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9.2 (46 Reviews)
Bed & Breakfast
  • Pet Friendly
  • View
  • Balcony/Terrace
Property Image From $170
         

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9.0 (49 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • View
Property Image From $152
         

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9.0 (9 Reviews)
House
  • Parking
  • Pet Friendly
  • View

Large Vacation Homes & Villas in Winchester

Over 11+ Large Vacation Homes & Villas in or Near Winchester
Property Image From $368
         

9.7 (28 Reviews)
House
  • Parking
  • View
  • Ocean View
Property Image From $173
         

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9.6 (426 Reviews)
Bed & Breakfast
  • Parking
  • Balcony/Terrace
  • Accessibility
Property Image From $158
         

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8.3 (114 Reviews)
Apartment
  • TV
  • Security/Safety
  • Guest Services
Property Image From $127
         

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7.8 (493 Reviews)
Apartment
  • Parking
  • Balcony/Terrace
  • Security/Safety
Property Image From $84
         

7.3 (16 Reviews)
Hostel
  • Accessibility
  • Security/Safety
  • Fireplace/Heating
Property Image From $363
         

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7.3 (15 Reviews)
Apartment
  • View
  • Accessibility
  • Security/Safety

Wheelchair Accessible Vacation Homes in Winchester

Over 10+ Wheelchair Accessible Vacation Homes in or Near Winchester
Property Image From $81
         

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8.4 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Property Image From $335
         

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New
Apartment
  • Parking
  • Wheelchair Accessible
  • Balcony/Terrace
Property Image From $213
         

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7.2 (147 Reviews)
House
  • Parking
  • Pet Friendly
  • View
Property Image From $113
         

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8.8 (899 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Property Image From $118
         

8.9 (1517 Reviews)
Hotel
  • Wheelchair Accessible
  • Balcony/Terrace
  • Accessibility
Property Image From $70
         

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8.8 (3 Reviews)
Hotel
  • Parking
  • Wheelchair Accessible
  • Accessibility
Property Image From $150
         

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8.4 (2103 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $231
         

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8.1 (1063 Reviews)
Hotel
  • Parking
  • View
  • Wheelchair Accessible

Winchester Varoom and Airbnb Places to Stay Under $200

Over 59+ Winchester Varoom and Airbnb Places to Stay Under $200
Property Image From $167
         

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10.0 (1 Review)
Apartment
  • Parking
  • Security/Safety
  • Internet
Property Image From $119
         

10.0 (3 Reviews)
House
  • Parking
  • Balcony/Terrace
  • Security/Safety
Property Image From $170
         

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9.7 (3 Reviews)
Apartment
  • Security/Safety
  • Guest Services
  • Child Friendly
Property Image From $177
         

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9.6 (331 Reviews)
Bed & Breakfast
  • Parking
  • TV
  • Balcony/Terrace
Property Image From $175
         

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9.6 (120 Reviews)
Apartment
  • Parking
  • Security/Safety
  • Sports/Activities
Property Image From $137
         

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9.6 (38 Reviews)
Cabin
  • Parking
  • TV
  • Balcony/Terrace
Property Image From $184
         

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9.6 (80 Reviews)
House
  • Parking
  • View
  • Balcony/Terrace
Property Image From $165
         

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9.4 (23 Reviews)
House
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  • View
  • Balcony/Terrace

Instantly Bookable Vacation Homes in Winchester

Over 1+ Instantly Bookable Vacation Homes in or Near Winchester
Property Image From $287
         

New
Cabin
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities

About Winchester Vacation Rentals

With more than 155 Winchester vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Vacationhomelettings 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 Vacationhomelettings 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 500.24 ft² on average, with prices averaging $247 a night.

Vacationhomelettings 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
Holiday Apartments 49
Vacation Homes 49
Hotels with Suites 32
B&B 12
Cottages 5
Cabin Rentals 3
Others 3
Hostels 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Winchester

Pro Tip: Vacationhomelettings makes it easy to compare the best listings on Vacationhomelettings homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Vacationhomelettings 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 43°F       Low 32°F
March - May
High 61°F       Low 36°F
June - August
High 63°F       Low 48°F
September - November
High 58°F       Low 35°F