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.

Dec 28 – Jan 4

G$26,616 GYD per night

Guest favorite

Guesthouse in Hampshire

4.92 out of 5 average rating, 177 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 21 – 28

G$19,658 GYD per night

Guest favorite

Condo in Hampshire

4.96 out of 5 average rating, 111 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.

Sep 4 – 11

G$33,434 GYD per night

Guest favorite

Apartment in Hampshire

4.95 out of 5 average rating, 174 reviews

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).

Aug 1 – 8

G$33,268 GYD per night

Guest favorite

Guest suite in Hampshire

4.97 out of 5 average rating, 282 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.

G$17,317 GYD per night

Guest favorite

Home in Hampshire

4.96 out of 5 average rating, 547 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.

Aug 19 – 26

G$24,702 GYD per night

Guest favorite

Apartment in Winchester

4.91 out of 5 average rating, 290 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 28 – Aug 4

G$20,569 GYD per night

Guest favorite

Guesthouse in Winchester

4.97 out of 5 average rating, 463 reviews

Idyllic Hideaway Ham Green Cottage near Winchester

The Orchard Studio at Ham Green Cottage is a pretty brick and flint building tucked away in a corner of our truly English country garden. You are completely private. We are family-friendly and you can expect a comfortable stay and warm welcome. We are in a village close to the historic city of Winchester, however our setting is completely rural and quiet. We have a fantastic village pub or there are lots of places to chose from in Winchester itself - the best of both worlds!

Mar 22 – 29

G$31,619 GYD per night

Guest favorite

Farm stay in Hampshire

4.91 out of 5 average rating, 151 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.

Dec 15 – 22

G$16,388 GYD per night

Guest favorite

Guest suite in Winchester

4.89 out of 5 average rating, 141 reviews

Beautiful guest suite in rural Hampshire

Set in the grounds of a Grade II listed thatched cottage on the edge of Kings Worthy village, our annex is beautifully decorated and comfortable. With its own entrance and small private outdoor area, this property combines rural charm and handy local amenities (bus stop just outside to central Winchester and fantastic local pub just a two minute walk away). Tea and coffee are provided as well as breakfast cereals, bread/butter and fruit jams.

Oct 19 – 26

G$22,926 GYD per night

Guest favorite

Home in Hampshire

4.88 out of 5 average rating, 214 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.

Sep 24 – Oct 1

G$36,393 GYD per night

Guest favorite

Apartment in Winchester

4.95 out of 5 average rating, 235 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.

Jun 8 – 15

G$24,364 GYD 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

Farm stay in Headbourne Worthy

5.0 out of 5 average rating, 237 reviews

A Unique Farm Retreat

Nov 15 – 22

G$50,057 GYD per night

Guest favorite

Home in Meonstoke

5.0 out of 5 average rating, 115 reviews

The Piggery: with tennis court and games barn

Jan 12 – 19

G$38,068 GYD 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

Aug 12 – 19

G$21,895 GYD per night

Guest favorite

Condo in Hampshire

4.94 out of 5 average rating, 198 reviews

Lovely 2 Bedroom Flat

Aug 31 – Sep 7

G$24,759 GYD per night

Guest favorite

Home in Winchester

4.99 out of 5 average rating, 245 reviews

Martyr Worthy Home with a View

Dec 8 – 15

G$34,806 GYD per night

Guest favorite

Apartment in Compton

4.98 out of 5 average rating, 229 reviews

The Annexe at Longacre, near Winchester

Jan 20 – 27

G$25,273 GYD per night

Guest favorite

Tiny home in Winchester,

4.94 out of 5 average rating, 126 reviews

The Hidden house in Winchester

Dec 14 – 21

G$37,350 GYD per night

Guest favorite

Townhouse in Hampshire

4.99 out of 5 average rating, 169 reviews

Entire House Central Winchester 2bed private patio

Feb 28 – Mar 7

G$44,624 GYD 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 townhouse rentals in City of Winchester?
Experience the best of City of Winchester with our townhouse rentals, starting at about $30 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 420 vacation rentals in Netley, over 700 vacation rentals in Marchwood, over 1,130 vacation rentals in Ocean Village, and over 700 vacation rentals in Freemantle.
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 Shepherds Hut Rentals in City of Winchester?
Enhance your stay in our Shepherds Hut Rentals with the most popular amenities: over 20 homes with a kitchen, over 10 homes with wifi, over 20 homes with free parking, 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 house rentals in City of Winchester have free parking?
Absolutely! We offer over 580 house rentals with free parking in City of Winchester. Enjoy a tailored experience with all the comforts you desire.
Do townhouse rentals in City of Winchester have a kitchen?
Absolutely! We offer over 50 townhouse 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

Cabins

Bungalows

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

Farm stay in Headbourne Worthy

Home in Meonstoke

Apartment in Corhampton

Condo in Hampshire

Home in Winchester

Apartment in Compton

Tiny home in Winchester,

Townhouse in Hampshire

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 townhouse 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 Shepherds Hut 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 house rentals in City of Winchester have free parking?

Do townhouse rentals in City of Winchester have a kitchen?

Destinations to explore