Taos Valley Accommodations - Vacation Rentals in City of Winchester

Fairlawn From US $97
         

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9.4 (63 Reviews)
Bed & Breakfast
  • Parking
  • Wheelchair Accessible
  • Child Friendly
The Bugle Inn Twyford From US $154
         

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8.9 (215 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Hygge hideaway From US $157
         

10.0 (4 Reviews)
House
  • Parking
  • Accessibility
  • Security/Safety
Piping Green 5 bedroom House From US $465
         

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10.0 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • View
Lovington Barn From US $553
         

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10.0 (2 Reviews)
House
  • Parking
  • View
  • Security/Safety
The Stables, Wickham From US $319
         

10.0 (2 Reviews)
House
  • Parking
  • View
  • Security/Safety
Meon Boscage From US $536
         

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10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • View
House - Sleeps 8 - Parking - Garden From US $526
         

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10.0 (1 Review)
House
  • Parking
  • View
  • Security/Safety

Luxury Places to Stay in City of Winchester

Over 149+ Luxury Places to Stay in or Near City of Winchester
Coppice Hill House From US $833
         

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9.7 (4 Reviews)
House
  • Parking
  • Pet Friendly
  • View
The Kings Head From US $780
         

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8.8 (636 Reviews)
Bed & Breakfast
  • Parking
  • Pet Friendly
  • Balcony/Terrace
Lainston House From US $612
         

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9.0 (264 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • View
The Bakehouse - central townhouse sleeps 8 people From US $583
         

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6.6 (9 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Security/Safety
The Cart House From US $581
         

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9.4 (8 Reviews)
House
  • Parking
  • View
  • Accessibility

Top-Rated Vacation Rentals with a Pool in City of Winchester

Over 4+ Top-Rated Vacation Rentals with a Pool in or Near City of Winchester
The Winchester Hotel and Spa From US $148
         

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8.3 (2960 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Solent Hotel and Spa From US $181
         

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8.0 (1109 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
New Place From US $159
         

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7.8 (1925 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • Pool
Meon Valley Hotel, Spa & Golf From US $119
         

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6.9 (3125 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • Pool

Pet-Friendly Vacation Rentals in City of Winchester

Over 56+ Pet-Friendly Vacation Rentals in or Near City of Winchester
Peppercorn Cottage From US $463
         

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9.8 (11 Reviews)
House
  • Parking
  • Pet Friendly
  • View
The Old Cook House From US $152
         

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9.7 (4 Reviews)
House
  • Parking
  • Pet Friendly
  • View
Luxury City Centre Apartment, Winchester From US $289
         

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9.6 (11 Reviews)
Apartment
  • Pet Friendly
  • Accessibility
  • Security/Safety
The Shed @ Stares Farm Cottage From US $148
         

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9.5 (64 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • View
Nettlebed Farm Holiday Lets Barn3 From US $158
         

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9.5 (18 Reviews)
House
  • Parking
  • Pet Friendly
  • View
The Penthouse, Winchester From US $289
         

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9.5 (17 Reviews)
Apartment
  • Pet Friendly
  • Balcony/Terrace
  • Accessibility
Saskia's Rooms From US $180
         

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9.4 (71 Reviews)
Bed & Breakfast
  • Pet Friendly
  • View
  • Balcony/Terrace
Gorgeous Apartment in the centre of Winchester From US $191
         

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9.4 (19 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Security/Safety

Large Vacation Homes & Villas in City of Winchester

Over 12+ Large Vacation Homes & Villas in or Near City of Winchester
The Fox From US $173
         

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9.6 (426 Reviews)
Bed & Breakfast
  • Parking
  • Designated Smoking Area
  • Balcony/Terrace
South Winchester Lodges From US $340
         

9.2 (299 Reviews)
Cabin
  • Parking
  • Pet Friendly
  • View
The Lavender Folly - Cosy Accommodation Alresford From US $234
         

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8.8 (16 Reviews)
Villa
  • Security/Safety
  • Fireplace/Heating
  • Internet
Royal Swan, Ashley Manor - B&B From US $125
         

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8.5 (242 Reviews)
Bed & Breakfast
  • Parking
  • Pet Friendly
  • TV
Settle in Winchester - Stylish Self Check-In Rooms From US $195
         

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8.5 (230 Reviews)
Apartment
  • TV
  • Security/Safety
  • Guest Services
The Bucks Head From US $137
         

8.5 (88 Reviews)
Bed & Breakfast
  • Parking
  • TV
  • View
Winchester Apartments From US $127
         

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7.8 (346 Reviews)
Apartment
  • Parking
  • Balcony/Terrace
  • Security/Safety
For Students Only Cathedral Point in Winchester From US $84
         

7.3 (23 Reviews)
Hostel
  • Accessibility
  • Security/Safety
  • Fireplace/Heating

Wheelchair Accessible Vacation Homes in City of Winchester

Over 12+ Wheelchair Accessible Vacation Homes in or Near City of Winchester
Woodlands Cottage Farm From US $178
         

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9.8 (136 Reviews)
Bed & Breakfast
  • Parking
  • View
  • Wheelchair Accessible
Bright, modern & close to historic town From US $164
         

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9.8 (24 Reviews)
House
  • Parking
  • Designated Smoking Area
  • View
Bull Farm Studios From US $81
         

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8.2 (7 Reviews)
Apartment
  • Parking
  • Wheelchair Accessible
  • Balcony/Terrace
The Black Hole From US $118
         

9.0 (1139 Reviews)
Hotel
  • Designated Smoking Area
  • Wheelchair Accessible
  • Balcony/Terrace
voco Winchester Hotel & Spa by IHG From US $153
         

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8.5 (1881 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
The Swan Hotel, Alresford From US $159
         

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8.5 (659 Reviews)
Hotel
  • Designated Smoking Area
  • Wheelchair Accessible
  • Balcony/Terrace
Lodge at Solent From US $101
         

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8.2 (1455 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • View
Hotel du Vin Winchester From US $338
         

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8.2 (918 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • View

City of Winchester Vacation Rentals and Airbnb Places to Stay Under $200

Over 51+ City of Winchester Vacation Rentals and Airbnb Places to Stay Under $200
Holly Hill Apartments From US $127
         

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9.9 (26 Reviews)
Apartment
  • Parking
  • View
  • Balcony/Terrace
Aethelred Annexe - New Build with Full Amenities From US $106
         

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9.7 (66 Reviews)
Apartment
  • Parking
  • View
  • Security/Safety
Little Hawthorns From US $123
         

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9.7 (36 Reviews)
Apartment
  • View
  • Balcony/Terrace
  • Security/Safety
Kiln Cottage From US $152
         

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9.6 (48 Reviews)
House
  • Parking
  • View
  • Balcony/Terrace
Hang Your Hat From US $184
         

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9.5 (67 Reviews)
House
  • Parking
  • View
  • Balcony/Terrace
Writer's Retreat From US $129
         

9.5 (4 Reviews)
Apartment
  • Parking
  • View
  • Balcony/Terrace
The Apartment, 24 West End Terrace, Winchester From US $66
         

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9.4 (95 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Designated Smoking Area

About City of Winchester Vacation Rentals

With more than 158 City of Winchester vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Taos Valley 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 City of Winchester.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Taos Valley City of 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 City of Winchester. Places to stay near City of Winchester are 578.11 ft² on average, with prices averaging US $257 a night.

Taos Valley makes it easy and safe to find and compare vacation rentals in City of 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 City of Winchester

Type Count
Vacation Homes 58
Holiday Apartments 49
Hotels 29
B&B 11
Others 4
Cabin Rentals 2
Villas 2
Hostels 1
Resorts 1
Ski Chalet Rentals 1

Use these Quick Filters to Find a Vacation Rental in City of Winchester

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

Weather in City of Winchester

View the weather forecast for City of Winchester before booking your City of 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

City of Winchester Vacation Rental Frequently Asked Questions

What are the top vacation rentals in City of Winchester?

There are a lot of options in City of Winchester. If you plan on staying in the City of Winchester area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in City of Winchester:

Which vacation homes in City of Winchester are best for families?

If you are looking for a family-friendly vacation home in City of 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 City of Winchester:

How many vacation rentals are available in City of Winchester?

Currently, the total number of properties listed in 2026 is over 158 in the City of Winchester area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in City of Winchester.