Guesthouse vacation rentals in City of Winchester

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in City of Winchester

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

0 of 0 items showing

1 of 3 pages

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.

Nov 3 – 10

R2,384 ZAR 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 17 – 24

R1,834 ZAR per night

Guest favorite

Guesthouse in Hampshire

4.94 out of 5 average rating, 163 reviews

IMMACULATELY PRESENTED COUNTRY BARN FOR UP TO FOUR

This traditional style country barn is nestled in the beautiful Meon Valley within minutes of Jane Austen's home and surrounded by stunning Hampshire countryside that offers extensive walking and cycling routes, and some great pubs. Within a 20 min radius are the market towns of Alresford, Farnham, Petersfield and Winchester. The accommodation is very well presented, albeit a compact kitchen/living area, with a super king size bed in the spacious master bedroom which is accessed via a twin room.

Jan 21 – 28

R2,509 ZAR per night

Guest favorite

Guesthouse in Froxfield

4.99 out of 5 average rating, 220 reviews

The Granary, self-contained B&B near Petersfield

The Granary is a little, self-contained cottage attached to the main house but with its own entrance, deck and BBQ area. Opposite our organic, sourdough bakery and set amidst beautiful gardens (croquet, hens, sunken trampoline, huge oaks) with footpaths, cycle routes and lanes into the national park, it is quiet, cosy and special. Choose your breakfast loaf direct from the bakery to enjoy with all the other bountiful and delicious ingredients supplied for you in your own, well equipped kitchen.

Sep 18 – 25

R2,545 ZAR per night

Guest favorite

Guesthouse in Warsash

4.96 out of 5 average rating, 150 reviews

Primrose Cottage Annexe, Self contained space

Primrose Cottage Annexe is a newly converted detached property compromising of lounge, bedroom and bathroom. Offering complete privacy and separate entrance from the main property it is a great place to relax overlooking our garden which is full of wildlife. In the heart of Warsash the property is 5 minutes walk from Warsash Sailing club, Maritime Academy and 3 great pubs. Also a 10 minute drive to Whiteley Business Park, Shopping, NATS making it a great base whilst away for work or leisure

Dec 18 – 25

R1,751 ZAR per night

Guest favorite

Guesthouse in Holybourne

4.97 out of 5 average rating, 119 reviews

Private, peaceful Annexe in rural Hampshire

Ground floor annexe located in the picturesque countryside village of Holybourne, near Alton. The entire self-contained annexe is for your use for the duration of your stay. It is attached to the main house and has its own front door for private use by guests. It is spacious and bright with a private garden for guests to enjoy. The perfect base to explore glorious Hampshire countryside with its many walking routes and cycle paths, or visit the nearby Watercress Line and Jane Austen’s House.

Aug 25 – Sep 1

R2,412 ZAR per night

Guest favorite

Guesthouse in Hampshire

4.95 out of 5 average rating, 139 reviews

The Old Cart Shed

This brick and flint barn has recently been converted to a smart modern annex next to our house. Set in the beautiful hamlet of Middle Preshaw in the heart of the South Downs National Park on The Monarch's Way footpath, just off The South Downs Way. A great base to explore Winchester, Winchester Christmas Market, the South Downs National Park, the South Coast for a sailing weekend, Southampton Boat Show, Goodwood Festival of Speed, and the New Forest. 50Mbps superfast wireless internet

Oct 7 – 14

R1,995 ZAR 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!

Jan 6 – 13

R2,835 ZAR per night

Guest favorite

Guesthouse in Overton

4.96 out of 5 average rating, 205 reviews

Private Annexe in Overton, Hampshire

This accommodation is a self contained annex which is located in the rear garden of the main property. It includes a bedroom with two single beds, a living area with TV including Sky Q (sports, cinema and kids) and free WiFi access. The kitchen includes an electric oven with hob and fridge freezer. There will be a small selection of tea and coffee on arrival. There is no facility for washing clothes. The bathroom includes a toilet, sink and shower.

Jun 11 – 18

R1,486 ZAR per night

Guest favorite

Guesthouse in Shawford

4.83 out of 5 average rating, 167 reviews

Spacious one bed annex, Shawford, Winchester

New self contained 2 storey annex with parking! Ideally located close to Winchester (3 miles) with Shawford train station being a 10 minute walk away through the beautiful Shawford Down. The M3 is also only 3 minutes away. There are two great pubs each no more than 15 minutes walk away. The Annex is beautifully finished, well equipped and with WiFi and NOW tv (SKY) to keep you connected. Our place would suit couples or business visitors.

Oct 19 – 26

R1,683 ZAR per night

Guest favorite

Guesthouse in Sutton Scotney, Hampshire

4.99 out of 5 average rating, 170 reviews

The Old Studio

A modern, chic converted Art studio in a quiet and secluded location in the heart of Hampshire. Eve and Nigel welcome you to this bright and airy, freshly designed space in the grounds of their beautiful village house. The Old Studio is cleverly designed to be used both as a whole or as two separate one bedroom apartments. Please contact us for more information about this.

Oct 1 – 8

R3,188 ZAR per night

Guest favorite

Guesthouse in Kings Worthy

4.95 out of 5 average rating, 128 reviews

Little Lansker : Country two-bed annexe

Little Lansker is a two bedroom self-contained annexe situated on the grounds of our home five miles from the historic city of Winchester. The property is nestled in the countryside on a working dairy farm. It's perfectly located for walkers, cyclists and people who are keen to enjoy Winchester's rich history and beautiful city.

May 17 – 24

R3,433 ZAR per night