Vacation rentals in City of Winchester

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Top-rated vacation rentals in City of Winchester

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Guest favorite

Guesthouse in Winchester

4.95 out of 5 average rating, 260 reviews

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.

Jan 10 – 17

$109 per night

Guest favorite

Guesthouse in Hampshire

4.92 out of 5 average rating, 176 reviews

Beautiful Self Contained Annex in South Downs NP

This brick and flint barn has been converted to a smart modern annex separate to our house. Set in the beautiful village of Meonstoke in the heart of the Meon Valley and the South Downs National Park. Ideal for visitors wanting a little luxury at the end of a day of outdoor pursuits. A really comfortable bed with blackout blinds and ensuite shower room. A spacious living area, with kitchen, dining area & log burning stove. Free wifi. Coffee (Nespresso machine) and tea, bread and jams included.

Jul 16 – 23

$83 per night

Guest favorite

Condo in Hampshire

4.96 out of 5 average rating, 108 reviews

Lovely 1 bedroom apartment with private parking

Lovely 1st floor 1 bedroom apartment with private entrance and secure free parking. CCTV covering entrance. Only 200m from the railway station and a 10 minute walk to the City centre. Immaculately decorated throughout. A fully equipped kitchen with welcome pack. 200Mbit WiFi. SmartTV. Gas central heating. King size bed with 100% cotton duvet cover. The pillows and duvet are duck feather and down. White cotton towels. Hairdryer, Iron & board. 100m from coffee shops and a pizza restaurant.

Dec 27 – Jan 3

$130 per night

Guest favorite

Farm stay in Headbourne Worthy

5.0 out of 5 average rating, 235 reviews

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 30 – Feb 6

$185 per night

Guest favorite

Guest suite in Hampshire

4.97 out of 5 average rating, 281 reviews

Own Front Door

Welcome to the beautiful city of Winchester! I have self contained central accommodation comprising of a double bedroom with en-suite shower room, a lounge with fridge/tea/coffee making facilities and your own private front door accessed from the street at ground level. The accommodation has been part of a massive renovation of the main house, now fully completed. Dating from the 1850’s it still retains a Victorian feel with high ceilings and sash windows. It is a lovely light, airy space.

Jul 8 – 13

$93 per night

Guest favorite

Home in Meonstoke

5.0 out of 5 average rating, 114 reviews

The Piggery: with tennis court and games barn

The Piggery is a secluded flint built hideaway, with lots of period charm, set in the grounds of a manor house. Converted to a high standard it has it’s own private garden, access to the owners tennis court & a large barn with table tennis, table football & pool, wider house grounds including an island, surrounded by the river Meon. Numerous walks direct from The Piggery and a number of local vineyards are nearby. 5/10mins walk away are two super pubs and the very well stocked village shop.

Dec 12 – 19

$158 per night

Guest favorite

Home in Hampshire

4.96 out of 5 average rating, 544 reviews

Quiet Winchester One Bedroom Home with own parking

Welcome to your lovely detached one bedroom home in a quiet leafy private road on the edge of St Giles Hill - just above medieval Winchester and on the edge of beautiful the South Downs Way. Your self-contained home includes parking on the drive, a stylish double bedroom, shower room, living area (with full double-width sofa bed) incorpoating a full kitchen/washing machine. Its an easy 10 minute downhill stroll across the park (lovely for a sunset picnic) to historic Winchester.

May 12 – 17

$100 per night

Guest favorite

Apartment in Winchester

4.91 out of 5 average rating, 287 reviews

The Loft with free off road parking

A self-contained studio by apartment with kitchen facilities, double bed, sofa and TV. En-suite toilet and shower room. Free off street parking on the doorstep. Situated 5-10 minutes walk from Winchester's historic city centre and even closer to the widely renowned Black Boy pub. Within 150 metres of the South Downs Way. Just a few minutes walk from the Winchester Sports Centre. The apartment is accessed via an external staircase and so may not suit those with mobility issues.

Jul 9 – 16

$86 per night

Guest favorite

Apartment in Compton

4.98 out of 5 average rating, 228 reviews

The Annexe at Longacre, near Winchester

The Annexe is a bright and airy self contained house separate from our home. The accomodation is over two floors with wonderful views out to the Hampshire countryside. We are on a quiet private country road 2 miles from the vibrant city of Winchester, 6 miles from Southampton Airport and 3 miles from IBM Hursley. Excellent transport links to London (1 hour from Shawford Station) and to Southampton. We live in the main house. Follow us on Instagram @longacreannexe

Feb 12 – 19

$106 per night

Guest favorite

Farm stay in Hampshire

4.9 out of 5 average rating, 147 reviews

Room with a view

You’ll love sharing photos of this unique place with your friends. Room with a View is a cosy and bright studio room located in the outskirts of the rural village of Owslebury. Just a 5-mile drive from the medieval city of Winchester, Room with a View is situated in a prime location, perfect for a serene getaway or business stay. Secluded from the busy bustle of the city, yet a swift 10-minute drive, Room with a View is surrounded by acres of fields and beautiful views.

Oct 30 – Nov 6

$69 per night

Guest favorite

Home in Hampshire

4.88 out of 5 average rating, 211 reviews

City Centre Riverside Gem With Parking.

An amazing two bedroom period cottage that is superbly located for all of Winchester's amenities, adjacent to the city mill and just a few steps away from the High Street. The cottage offers city living in a delightful tucked away location backing onto the River Itchen and only seconds from all the city centre has to offer. The house suits all needs, a romantic weekend, a South Downs Way stop over, family break and equally a business trip.

Jan 9 – 16

$155 per night

Guest favorite

Apartment in Winchester

4.95 out of 5 average rating, 232 reviews

Central Winchester garden flat, permit parking

Winchester City Centre- Bijou, charming, characterful, homely, warm and cosy self contained one bedroom flat with free permit parking and luxuriously large bath tub with shower, private garden with patio for alfresco dining. Fully equipped galley kitchen for self - catering. Only a five minute level walk to the central High Street and Cathedral. Less than ten minutes walk from the Railway Station.

May 11 – 18

$102 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for City of Winchester vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near City of Winchester's top sights

Marwell Zoo176 locals recommend

Westquay Shopping Centre61 locals recommend

Southampton Common52 locals recommend

St Mary's Stadium19 locals recommend

Mayflower Theatre91 locals recommend

Royal Victoria Country Park49 locals recommend

Other great vacation rentals in City of Winchester

Guest favorite

Guesthouse in New Alresford

4.93 out of 5 average rating, 239 reviews

17th century cottage Georgian town

Aug 5 – 12

$119 per night

Guest favorite

Townhouse in Hampshire

4.99 out of 5 average rating, 166 reviews

Entire House Central Winchester 2bed private patio

Feb 22 – Mar 1

$187 per night

Guest favorite

Guest suite in Hampshire

4.95 out of 5 average rating, 130 reviews

Pretty self contained annexe

Aug 7 – 14

$64 per night

Guest favorite

Guesthouse in Winchester

4.97 out of 5 average rating, 462 reviews

Idyllic Hideaway Ham Green Cottage near Winchester

Nov 5 – 12

$132 per night

Guest favorite

Apartment in Hampshire

4.95 out of 5 average rating, 174 reviews

Romantic, artist’s flat, superb central location.

Aug 19 – 26

$155 per night

Guest favorite

Guesthouse in Sparsholt

4.96 out of 5 average rating, 464 reviews

Rural retreat very near Winchester

Jun 1 – 8

$111 per night

Guest favorite

Apartment in Corhampton

4.94 out of 5 average rating, 176 reviews

Beautiful 1 BR flat 5 min walk to South Downs Way

May 9 – 16

$90 per night

Guest favorite

Cottage in Bishop's Waltham

4.98 out of 5 average rating, 122 reviews

Beautiful garden house, edge of town & South Downs

Oct 10 – 17

$103 per night

Show all

Quick stats about vacation rentals in City of Winchester

Total rentals
2.4K properties
Rentals with dedicated workspaces
1.2K properties have a dedicated workspace
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
540 properties allow pets
Family-friendly rentals
920 properties are a good fit for families
Total number of reviews
90K reviews

Frequently Asked Questions

How much does it cost to stay in cabin rentals in City of Winchester?
Experience the best of City of Winchester with our cabin rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Where should I stay in City of Winchester?
Make yourself at home in City of Winchester by choosing from our most frequently booked neighborhoods. We have over 700 vacation rentals in Freemantle, over 1,130 vacation rentals in Ocean Village, over 420 vacation rentals in Netley, and over 700 vacation rentals in Marchwood.
Do apartment rentals in City of Winchester have air conditioning?
Absolutely! We offer over 20 apartment rentals with air conditioning in City of Winchester. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in City of Winchester?
Four-legged friends are welcome in City of Winchester. Choose from more than 540 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in City of Winchester?
Yes! Work meets play with ease at over 1,180 vacation rentals in City of Winchester featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for Tiny House Rentals in City of Winchester?
Enhance your stay in our Tiny House Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with wifi, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there City of Winchester vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in City of Winchester, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly vacation rentals in City of Winchester?
City of Winchester has more than 920 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do cabin rentals in City of Winchester have free parking?
Absolutely! We offer over 30 cabin rentals with free parking in City of Winchester. Enjoy a tailored experience with all the comforts you desire.
Do loft rentals in City of Winchester have a kitchen?
Absolutely! We offer over 10 loft rentals with a kitchen in City of Winchester. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in City of Winchester

Top-rated vacation rentals in City of Winchester

Vacation rentals for every style

Bungalows

Cabins

Houses

Popular amenities for City of Winchester vacation rentals

Stay near City of Winchester's top sights

Other great vacation rentals in City of Winchester

Guesthouse in New Alresford

Townhouse in Hampshire

Guest suite in Hampshire

Guesthouse in Winchester

Apartment in Hampshire

Guesthouse in Sparsholt

Apartment in Corhampton

Cottage in Bishop's Waltham

Quick stats about vacation rentals in City of Winchester

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

How much does it cost to stay in cabin rentals in City of Winchester?

Where should I stay in City of Winchester?

Do apartment rentals in City of Winchester have air conditioning?

Are there pet-friendly vacation rentals in City of Winchester?

Are there vacation rentals with a dedicated workspace in City of Winchester?

What are the most popular amenities for Tiny House Rentals in City of Winchester?

Are there City of Winchester vacation rentals on Airbnb with pools?

Are there family-friendly vacation rentals in City of Winchester?

Do cabin rentals in City of Winchester have free parking?

Do loft rentals in City of Winchester have a kitchen?

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