Karen's Country Cottage - Vacation Rentals in City of Winchester

Hang Your Hat - The Cottage From US $220
         

10.0 (30 Reviews)
Cottage
  • Parking
  • TV
  • Balcony/Terrace
Woodlands Cottage Farm From US $178
         

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9.8 (136 Reviews)
Bed & Breakfast
  • Parking
  • View
  • Wheelchair Accessible
The Nestle House From US $335
         

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10.0 (4 Reviews)
Cottage
  • Parking
  • Balcony/Terrace
  • Security/Safety
2 bedroom accommodation in Cheriton From US $434
         

10.0 (9 Reviews)
Cottage
  • Parking
  • Pet Friendly
  • Balcony/Terrace
2 bedroom accommodation in Winchester From US $276
         

10.0 (6 Reviews)
Cottage
  • Parking
  • TV
  • Balcony/Terrace
The Nestle House City Centre Luxury From US $260
         

10.0 (5 Reviews)
Cottage
  • TV
  • Balcony/Terrace
  • Security/Safety
2 bedroom accommodation in Winchester From US $232
         

10.0 (2 Reviews)
Cottage
  • Parking
  • Pet Friendly
  • TV

Luxury Places to Stay in City of Winchester

Over 412+ Luxury Places to Stay in or Near City of Winchester
Spitfire Lodge, Winchester From US $2,821
         

New
Cabin
  • Balcony/Terrace
  • Security/Safety
  • Wellness Facilities
Coppice Hill House From US $1,693
         

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New
Cottage
  • Parking
  • Pet Friendly
  • Balcony/Terrace
Barley Cottage From US $1,179
         

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New
Cottage
  • Parking
  • Pet Friendly
  • TV
Rivergem - Riverside Coach House From US $1,153
         

New
Cottage
  • Parking
  • Pet Friendly
  • Security/Safety
Birdsong House From US $1,066
         

10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • TV

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

Over 20+ Top-Rated Vacation Rentals with a Pool in or Near City of 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
Solent Hotel and Spa From US $140
         

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8.6 (971 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
New Place From US $90
         

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8.4 (1000 Reviews)
Hotel
  • Parking
  • Pool
  • TV
The Winchester Hotel and Spa From US $171
         

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8.3 (2960 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Solent Hotel and Spa From US $135
         

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

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7.8 (1944 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • Pool
Marwell Hotel Winchester South From US $107
         

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7.6 (1003 Reviews)
Hotel
  • Parking
  • Pool
  • TV

Pet-Friendly Vacation Rentals in City of Winchester

Over 122+ Pet-Friendly Vacation Rentals in or Near City of Winchester
Piping Green 5 bedroom House From US $465
         

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10.0 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • View
Squirrel's Leap From US $665
         

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New
Cottage
  • Parking
  • Pet Friendly
  • Balcony/Terrace
*New* Beautiful Meon Valley Family Home *Sleeps6* From US $423
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
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 City of Winchester

Over 38+ Large Vacation Homes & Villas in or Near City of Winchester
Lavender Folly - Cosy Accommodation Alresford From US $199
         

10.0 (1 Review)
Villa
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
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 City of Winchester

Over 22+ Wheelchair Accessible Vacation Homes in or Near City of Winchester
The Sky Penthouse, City Centre Luxury From US $266
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
Fairlawn From US $97
         

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9.4 (63 Reviews)
Bed & Breakfast
  • Parking
  • Wheelchair Accessible
  • Child Friendly
The Sky Penthouse From US $335
         

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New
Apartment
  • Parking
  • Wheelchair Accessible
  • Balcony/Terrace
Ideal city centre base for iconic sightseeing From US $200
         

New
Apartment
  • TV
  • Wheelchair Accessible
  • Bedding/Linens
The Bugle Inn Twyford From US $154
         

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8.9 (215 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Lodge at Solent From US $96
         

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9.0 (981 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Cosy Georgian Bijou near Cathedral with Parking From US $187
         

5.0 (1 Review)
Apartment
  • Pet Friendly
  • Wheelchair Accessible
  • Balcony/Terrace
Bright, modern & close to historic town From US $164
         

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9.8 (24 Reviews)
House
  • Parking
  • Designated Smoking Area
  • View

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

Over 160+ City of Winchester Vacation Rentals and Airbnb Places to Stay Under $200
Luxury flat in the beautiful village of Botley From US $128
         

10.0 (1 Review)
Apartment
  • Parking
  • Security/Safety
  • Child Friendly
The Fox From US $159
         

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10.0 (192 Reviews)
Bed & Breakfast
  • Parking
  • Designated Smoking Area
  • Balcony/Terrace
NEW! Cosy house, a train spotter's delight From US $195
         

10.0 (5 Reviews)
House
  • Parking
  • TV
  • Balcony/Terrace
Luxury apartment in the beautiful village of Botley From US $198
         

10.0 (1 Review)
Apartment
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
Aethelred Annexe - New Build with Full Amenities From US $115
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Security/Safety
1 bedroom accommodation in Alresford From US $182
         

New
Ski Chalet
  • TV
  • Security/Safety
  • Fireplace/Heating
Lower Whiteflood Farm Cottage From US $165
         

New
Cottage
  • Parking
  • Pet Friendly
  • Balcony/Terrace

Instantly Bookable Vacation Homes in City of Winchester

Over 114+ Instantly Bookable Vacation Homes in or Near City of Winchester
Cosy A-Frame cabin nestled in the chalk steams of Hampshire From US $287
         

New
Cabin
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
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
Calm 1 Bed Apartment with Parking, Winchester by At Hem From US $205
         

About City of Winchester Vacation Rentals

With more than 63 City of Winchester vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Karenscountrycottage 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 Karenscountrycottage 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 311.95 ft² on average, with prices averaging US $405 a night.

Karenscountrycottage 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
Cottages 48
Vacation Homes 13
Holiday Apartments 1
B&B 1

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

Pro Tip: Karenscountrycottage makes it easy to compare the best listings on Karenscountrycottage homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Karenscountrycottage 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?
How many vacation rentals are available in City of Winchester?

Currently, the total number of properties listed in 2026 is over 63 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.