Winchester vacation rentals

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Top-rated vacation rentals in Winchester

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite
Guesthouse in Winchester
Water Meadows Lodge beside Winchester South Downs
"Riverside" Garden Lodge is separate, secure and sunny with a private garden and free parking in St Cross village Winchester, beside the Water Meadows and South Downs. Only 15 minutes walk from the centre via the famous Water Meadow paths or road's celebrated inns you have an ideal location to enjoy this historic city. Finished to high standards, the double bedroom, spacious living / dining room, kitchen, shower / loo have the essential luxuries. Plus Fast WiFi, 42" Smart TV and Laundry service.
Nov 5 – 12
G$19,525 GYD per night
4.95 out of 5 average rating, 260 reviews
Guest favorite
Farm stay in Headbourne Worthy
A Unique Farm Retreat
There’s something magical about The Granary. Set in acres of farmland with spectacular sunrises and sunsets, The Granary brims with rustic charm. A dreamy hideaway with an outdoor copper bath and wood fired hot tub. An idyllic get-away-from-it-all yet only 3 miles to historic Winchester. Soak amid hot water, steam and fresh air surrounded by nature and birdsong, enjoy magnificent sunsets from the ‘Sundowner’ or cosy up toasting marshmallows over the fire pit - a perfect escape to unwind.
Jan 22 – 29
G$39,568 GYD per night
5.0 out of 5 average rating, 224 reviews
Guest favorite
Apartment in Hampshire
Romantic, artist’s flat, superb central location.
Romantic, bow-fronted, ground floor Regency property with lots of character. Well-appointed but down to earth. Directly opposite the famous King Alfred's statue in the centre of town: 1 minute walk to the river, 1 minute to city centre shops, 3 mins to Winchester Cathedral, 15 mins to train station. Kitchen opens into small pretty garden, then onto quiet cul-de sac for parking (permit provided- parking in the cul-de-sac not guaranteed but there are plenty of streets within the permit zones).
Jun 13 – 20
G$30,369 GYD per night
4.95 out of 5 average rating, 170 reviews

Popular amenities for Winchester vacation rentals

Stay near Winchester's top sights

The Great Hall55 locals recommend
Sainsbury's7 locals recommend
Winchester Christmas Market11 locals recommend
St Catherine's Hill55 locals recommend
Theatre Royal Winchester41 locals recommend
The Old Vine21 locals recommend

Other great vacation rentals in Winchester

Guest favorite
Loft in Charlecote
Beautiful Apartment in Centre of Winchester
Dec 6 – 13
G$30,077 GYD per night
4.92 out of 5 average rating, 157 reviews
Guest favorite
Guesthouse in Hampshire
The Lodge Winchester
Jul 22 – 29
G$31,893 GYD per night
4.97 out of 5 average rating, 145 reviews
Guest favorite
Shepherd’s hut in Winchester
Shepherd's Hut with Hot Tub near Winchester
Jul 27 – Aug 3
G$26,815 GYD per night
4.96 out of 5 average rating, 323 reviews
Guest favorite
Cottage in Winchester
Beggar's Lane Cottage-3 beds in Central Winchester
Aug 15 – 22
G$34,374 GYD per night
4.82 out of 5 average rating, 244 reviews
Guest favorite
Guesthouse in Hampshire
Cosy Annexe in a beautiful part of Winchester
Jun 14 – 21
G$17,912 GYD per night
4.9 out of 5 average rating, 303 reviews
Guest favorite
Apartment in Compton
The Annexe at Longacre, near Winchester
Feb 10 – 17
G$22,412 GYD per night
4.98 out of 5 average rating, 223 reviews
Guest favorite
Hut in Winchester
The Pigsty
Aug 23 – 30
G$42,776 GYD per night
4.97 out of 5 average rating, 452 reviews
Guest favorite
Home in Winchester
Martyr Worthy Home with a View
Nov 7 – 14
G$31,280 GYD per night
4.99 out of 5 average rating, 241 reviews
Guest favorite
Guest suite in Hampshire
Pretty self contained annexe
Aug 31 – Sep 7
G$14,093 GYD per night
4.95 out of 5 average rating, 123 reviews
Guest favorite
Apartment in Winchester
City Apartment
Jul 28 – Aug 4
G$36,436 GYD per night
4.99 out of 5 average rating, 116 reviews
Guest favorite
Condo in Hampshire
Lovely 2 Bedroom Flat
Jun 16 – 23
G$22,137 GYD per night
4.95 out of 5 average rating, 187 reviews
Guest favorite
Farm stay in Hampshire
Room with a view
Nov 25 – Dec 2
G$14,704 GYD per night
4.9 out of 5 average rating, 142 reviews

Other great vacation rentals in Winchester

Guest favorite
Barn in Broughton
The Barn in Broughton
May 9 – 16
G$23,527 GYD per night
4.99 out of 5 average rating, 166 reviews
Guest favorite
Hut in Winchester
Nature’s Nook Cosy Couples Woodland Cabin Hursley
Apr 9 – 16
G$37,582 GYD per night
5.0 out of 5 average rating, 151 reviews
Guest favorite
Cottage in Privett
The Barn @ North Lodge -Soho Farmhouse-esque Cabin
Nov 29 – Dec 6
G$24,511 GYD per night
4.97 out of 5 average rating, 402 reviews
Guest favorite
Home in Crawley
Secluded and peaceful home in beautiful village
Jun 11 – 18
G$23,112 GYD per night
4.96 out of 5 average rating, 265 reviews
Guest favorite
Guesthouse in Hampshire
Beautiful Self Contained Annex in South Downs NP
May 5 – 12
G$17,541 GYD per night
4.92 out of 5 average rating, 170 reviews
Guest favorite
Guest suite in Hampshire
The Oaks, Twyford Moors, South Downs National Park
Aug 10 – 17
G$22,595 GYD per night
4.96 out of 5 average rating, 242 reviews
Guest favorite
Apartment in Alresford
Stunning apartment in the heart of New Alresford
Nov 14 – 21
G$21,947 GYD per night
4.93 out of 5 average rating, 106 reviews
Guest favorite
Apartment in Hampshire
Flat in central Winchester
Jul 24 – 31
G$24,778 GYD per night
4.86 out of 5 average rating, 22 reviews
Guest favorite
Condo in Hampshire
Bright Bijou Studio in Central Winchester
Apr 28 – May 5
G$22,152 GYD per night
4.93 out of 5 average rating, 89 reviews
Guest favorite
Condo in Hampshire
Spacious Central Winchester 1 Bedroom Flat
Dec 31 – Jan 7
G$20,452 GYD per night
5.0 out of 5 average rating, 26 reviews
Guest favorite
Apartment in Hampshire
Stylish, comfortable flat in central Winchester
Sep 20 – 27
G$29,409 GYD per night
4.91 out of 5 average rating, 44 reviews
Guest favorite
Condo in Winchester
Lovely 1 bedroom flat in Winchester with parking
Aug 19 – 26
G$20,681 GYD per night
4.92 out of 5 average rating, 73 reviews

Quick stats about vacation rentals in Winchester

Total rentals

310 properties

Wifi availability

300 properties include access to wifi

Rentals with dedicated workspaces

120 properties have a dedicated workspace

Pet-friendly rentals

80 properties allow pets

Family-friendly rentals

150 properties are a good fit for families

Total number of reviews

16K reviews

Frequently Asked Questions

  • What are some of the best things to do in Winchester?

    Take a walk through the vibrant Winchester Farmers Market, visit Winchester Science Centre for interactive exhibits, or explore Winchester College, one of the oldest schools in the country. For a touch of culture, visit the Theatre Royal Winchester for a performance.

  • What is the best time of year to visit Winchester?

    Many visitors explore Winchester from June to August when there's plenty of sunshine and the Winchester Hat Fair, a free outdoor arts festival, enlivens the city. Another popular time is during the Winchester Christmas Market in late November to December.

  • What are the best places to stay in Winchester?

    The city centre, with its proximity to historical sites and vibrant eateries, is a favourite amongst visitors. St. Cross, known for its peaceful ambiance, and Hyde, within walking distance of the city centre, are also popular. For a rural retreat, consider the surrounding Hampshire countryside.

  • What are the best places to visit in Winchester?

    Winchester Cathedral, one of the largest cathedrals in Europe, is often recommended. Other frequently suggested places include Winchester City Mill, a working watermill, and the Great Hall, home to King Arthur's Round Table. For history lovers, the Winchester City Museum is a must.

  • What are some hiking trails in Winchester?

    Explore the South Downs Way, a long-distance footpath spanning 100 miles (160 km), or the shorter but equally enjoyable St. Catherine's Hill, offering spectacular views of the city. Alternatively, immerse yourself in the natural beauty of the Itchen Navigation Heritage Trail, a serene walk along the Itchen River.

  • What are some family activities to do in Winchester?

    Families can enjoy a fun-filled day at Marwell Zoo, home to hundreds of exotic and endangered animals, or learn about the natural world at Winchester Science Centre. The interactive Winchester City Museum and the Military Museums are also popular with families.

  • What are some of the best day trip ideas in Winchester?

    Consider a day trip to the ancient Stonehenge, located about 40 miles (64 km) from Winchester. Another frequently suggested trip is to the beautiful New Forest National Park, just 23 miles (37 km) away. The historic city of Bath, known for its Roman-built baths, is also within reach at 54 miles (87 km).

  • Are there vacation rentals with a dedicated workspace in Winchester?

    Yes! Work meets play with ease at over 120 vacation rentals in Winchester featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Winchester?

    Four-legged friends are welcome in Winchester. Choose from more than 80 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in chalet rentals in Winchester?

    Experience the best of Winchester with our chalet rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Destinations to explore

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