Airport Express Hotel - Vacation Rentals in Winchester

Wykeham Arms From US $260
         

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9.1 (1003 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • View
The Cricketers Inn From US $222
         

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9.8 (27 Reviews)
Hotel
  • Parking
  • Designated Smoking Area
  • Balcony/Terrace
The Black Hole From US $118
         

9.0 (1139 Reviews)
Hotel
  • Designated Smoking Area
  • Wheelchair Accessible
  • Balcony/Terrace
The Old Vine From US $240
         

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9.6 (230 Reviews)
Hotel
  • Parking
  • TV
  • Balcony/Terrace
The Plough Itchen Abbas From US $137
         

9.0 (964 Reviews)
Hotel
  • Parking
  • Designated Smoking Area
  • View
Wykeham Arms From US $206
         

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9.4 (416 Reviews)
Hotel
  • Parking
  • TV
  • Balcony/Terrace
The Old Vine From US $303
         

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9.0 (745 Reviews)
Hotel
  • Parking
  • Balcony/Terrace
  • Security/Safety
Kyoto Rooms From US $110
         

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9.2 (71 Reviews)
Hotel
  • Security/Safety
  • Restaurant
  • Bar

Luxury Places to Stay in Winchester

Over 298+ Luxury Places to Stay in or Near Winchester
Spitfire Lodge, Winchester From US $2,821
         

New
Cabin
  • Balcony/Terrace
  • Security/Safety
  • Wellness Facilities
Rivergem - Riverside Coach House From US $1,153
         

New
Cottage
  • Parking
  • Pet Friendly
  • Security/Safety
Birdsong House From US $1,075
         

10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • TV
The Kings Head From US $780
         

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8.8 (636 Reviews)
Bed & Breakfast
  • Parking
  • Pet Friendly
  • Balcony/Terrace
Fully renovated townhouse in heart of Winchester's cathedral streets From US $666
         

10.0 (4 Reviews)
House
  • Balcony/Terrace
  • Security/Safety
  • Bedding/Linens

Top-Rated Vacation Rentals with a Pool in Winchester

Over 12+ Top-Rated Vacation Rentals with a Pool in or Near Winchester
31 Queens Road From US $133
         

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9.0 (223 Reviews)
Bed & Breakfast
  • Parking
  • Pool
  • Balcony/Terrace
The Winchester Hotel & Spa From US $172
         

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8.6 (1005 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
The Winchester Hotel and Spa From US $171
         

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8.3 (2960 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Marwell Hotel Winchester South From US $107
         

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7.6 (1003 Reviews)
Hotel
  • Parking
  • Pool
  • TV
New
House
  • Parking
  • Pool
  • Designated Smoking Area

Pet-Friendly Vacation Rentals in Winchester

Over 85+ Pet-Friendly Vacation Rentals in or Near Winchester
Piping Green 5 bedroom House From US $465
         

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10.0 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • View
No. 32 Upper High Street WestgateCottage From US $210
         

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10.0 (1 Review)
Cottage
  • Parking
  • Pet Friendly
  • TV
2 bedroom accommodation in Winchester From US $234
         

10.0 (2 Reviews)
Cottage
  • Parking
  • Pet Friendly
  • TV
RIVERGEM - RIVERSIDE COACH HOUSE, pet friendly in Winchester From US $404
         

10.0 (1 Review)
Cottage
  • Parking
  • Pet Friendly
  • Balcony/Terrace

Large Vacation Homes & Villas in Winchester

Over 23+ Large Vacation Homes & Villas in or Near Winchester
House - Sleeps 8 - Parking - Garden From US $526
         

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10.0 (1 Review)
House
  • Parking
  • View
  • Security/Safety
Host & Stay | Combpyne From US $473
         

New
House
  • Balcony/Terrace
  • Security/Safety
  • Sports/Activities
4 Bedroom Gateway: Winchester - Town Centre 4 mins. From US $504
         

10.0 (2 Reviews)
House
  • Pet Friendly
  • Security/Safety
  • Bedding/Linens

Wheelchair Accessible Vacation Homes in Winchester

Over 15+ Wheelchair Accessible Vacation Homes in or Near Winchester
The Bugle Inn Twyford From US $154
         

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8.9 (215 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
The Sky Penthouse From US $335
         

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New
Apartment
  • Parking
  • Wheelchair Accessible
  • Balcony/Terrace
The Sky Penthouse, City Centre Luxury From US $265
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
Bull Farm Studios From US $81
         

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8.2 (7 Reviews)
Apartment
  • Parking
  • Wheelchair Accessible
  • Balcony/Terrace
voco Winchester Hotel & Spa by IHG From US $124
         

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8.8 (997 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Ideal city centre base for iconic sightseeing From US $200
         

New
Apartment
  • TV
  • Wheelchair Accessible
  • Bedding/Linens
Lainston House From US $612
         

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9.0 (264 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • View
Premier Inn Winchester From US $69
         

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8.8 (10 Reviews)
Hotel
  • Parking
  • Wheelchair Accessible
  • Accessibility

Winchester Vacation Rentals and Airbnb Places to Stay Under $200

Over 106+ Winchester Vacation Rentals and Airbnb Places to Stay Under $200
Aethelred Annexe - New Build with Full Amenities From US $106
         

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9.7 (50 Reviews)
Apartment
  • Parking
  • Security/Safety
  • Guest Services
The Fox From US $165
         

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10.0 (185 Reviews)
Bed & Breakfast
  • Parking
  • Designated Smoking Area
  • Balcony/Terrace
Aethelred Annexe - New Build with Full Amenities From US $115
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Security/Safety
31 Queens Road Rental - Self-contained Apartment From US $168
         

Lower Whiteflood Farm Cottage From US $167
         

New
Cottage
  • Parking
  • Pet Friendly
  • Balcony/Terrace
Garden room, central Winchester From US $155
         

New
Apartment
  • Parking
  • TV
  • Security/Safety
Contemporary apartment in central Winchester From US $128
         

9.4 (43 Reviews)
Apartment
  • Parking
  • TV
  • Balcony/Terrace

Instantly Bookable Vacation Homes in Winchester

Over 78+ Instantly Bookable Vacation Homes in or Near Winchester
Cosy A-Frame cabin nestled in the chalk steams of Hampshire From US $287
         

New
Cabin
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
Hang Your Hat - The Cottage From US $220
         

10.0 (30 Reviews)
Cottage
  • Parking
  • TV
  • Balcony/Terrace
2 bedroom accommodation in Winchester From US $295
         

10.0 (6 Reviews)
Cottage
  • Parking
  • TV
  • Balcony/Terrace
The Nestle House City Centre Luxury From US $300
         

10.0 (5 Reviews)
Cottage
  • TV
  • Balcony/Terrace
  • Security/Safety
Luxury 3 bedroom Scandinavian Lodge v(sleeps 6) From US $365
         

Stylish 3BD Townhouse in Central Winchester From US $482
         

10.0 (1 Review)
House
  • TV
  • Balcony/Terrace
  • Security/Safety

About Winchester Vacation Rentals

With more than 37 Winchester vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Airportexpresshotel 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 Airportexpresshotel 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 101.46 ft² on average, with prices averaging US $178 a night.

Airportexpresshotel 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
Hotels 37

Use these Quick Filters to Find a Vacation Rental in Winchester

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

Winchester Vacation Rental Frequently Asked Questions

Which vacation homes in Winchester are best for families?

If you are looking for a family-friendly vacation home in Winchester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winchester:

How many vacation rentals are available in Winchester?

Currently, the total number of properties listed in 2026 is over 37 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.