
Guest house holiday rentals in Winchester
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Top-rated guest house rentals in Winchester
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Central, Quiet & Self-Contained
Incredibly central location. Only 150m from Cathedral & 200m to High St. Quiet: Set back from the street, double glazing, detached building. King size bed with luxury mattress & topper, hypoallergenic duvet & pillows, Egyptian cotton bedlinen and fluffy towels. Work space. Reading & soft lighting. Well Equipped: Tea & Coffee Facilities, Mini Fridge, TV (Netflix only) Iron+Board, Hairdryer, Toiletries & Fan. Secure parking subject to availability £20per night. NB. Access via external staircase.

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.

Countryside Lodge in the heart of the South Downs
Highfield Bungalow sits in the heart of the South Downs, located on our own farmland, a light and airy single story building offering 3 bedrooms, family bathroom, fully fitted modern kitchen, dining area with large dining table, sofa and sofa bed for additional guests. There are stunning views of the surrounding countryside from the lounge area, bedrooms. The adjoining terrace is the perfect spot to dine al fresco whilst enjoying the views. The lawn area has a games store and private hot tub.

Guest House/Annex - fully self-contained
Self contained, detached guest house / annex. Small kitchen/diner at ground level and sleep/live studio space upstairs. Upstairs ensuite shower room and a laundry cupboard with washing machine. Off road, gated, parking in grounds of main family house and next to the annex. Easy driving (3 miles) from the charming town of Alresford and the cultural, historic city of Winchester (10 miles). There are plenty of lovely pubs for walks and lunches to keep you fed and watered for a fortnight!

Cabin with parking, ensuite, own entrance & garden
This beautiful self-contained little cabin has been custom made. You have a single-double extendable bed. Desk, microwave, fridge, hairdryer, crockery, toaster. Your own personal ensuite bathroom with shower. Direct access to the garden, and your own private entrance. This is a private peaceful space, with self check-in for greater flexibility. * If you are 2 guests please book for 2 people * Early or late check-ins need our agreement, notice helps us to be flexible where possible

The Annex - sleeps 2/3 people
Welcome to our spacious and modern annexe nestled in the charming village of Waltham Chase, Hampshire. Located near the historic market town of Bishop’s Waltham, guests can explore its rich heritage and vibrant atmosphere. Surrounded by picturesque countryside, with quaint country walls and inviting pubs nearby, our newly renovated annexe offers the perfect blend of comfort and convenience for a relaxing getaway. This stylish place to stay is perfect for couples or small families.

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!

Cosy annexe by Riverside Park
* Self-contained annexe - own entrance & parking for one car. * Close to Motorway, City Centre and Cruise Port (10 mins drive), Universities, St. Mary's stadium, Ageas Bowl, Southampton Airport and Peppa Pig World (20 mins drive). * Bus stop and train station is a few minutes walk away. * Bitterne Triangle (3 mins walk) has a bakery, coffee roasters, takeaways, cafes, a micropub, a Spar, Tesco Express and laundrette. * Riverside park offers a lovely walk along the river 🌳🦆

The Woodshed
The Woodshed is right in the heart of the South Downs National Park, between the villages of Warnford and Exton, a secluded and peaceful space surrounded by a working farm. The Woodshed has a view of Old Winchester Hill that is magic. Activities in the area include biking, hiking, and angling, and three of the best pubs in Hampshire are within a 5 mile radius. As we are a little distance from the main track, I am happy to come and collect guests from Exton if walking.

The Limes, Colden Common, Winchester, with parking
This quiet, spacious and comfortable ground floor annexe is situated in a rural village on the south side of Winchester. The Limes, with its own front door, offers a relaxing home from home environment. It is light and airy, set well back from the road, overlooking a lovely garden with views of the countryside. It offers off road parking, 15 minutes from Winchester centre, good size and comfortable double and single bedrooms, with a well equipped kitchen.

Stunning oak-framed "Loft House"
The "Loft House" was built in 2017 and has been freshly decorated to create a calm and stylish space. It is situated in a truly beautiful and tranquil rural location, and is a fantastic base to explore this lovely part of Hampshire. It is a cosy compact space so ideal for a couple or two adults, and could also accommodate up to two children. It is not suitable for more than two adults.

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.
Popular amenities for guest house rentals in Winchester
Family-friendly guest house rentals

Luxury Studio with Hot Tub & Sauna

Converted Granary, South Downs nr Goodwood

Peaceful annex in walking distance to the forest

Luxury self-contained annexe near Chichester

Self-contained studio Wokingham

Lockerley Log Cabin Guesthouse

Private Annexe in Overton, Hampshire

New Forest garden chalet.
Guest house rentals with a patio

Studio 114- 1 bedroom guest house.

The Nook - Forest/Coastal Luxury Studio

Seaside Cottage

Chic Studio & Courtyard | Walk to Pubs & Town

Peaceful one bedroom hideaway with hot tub

Self contained studio in Lower Bourne, Farnham

Cabin in the Forest

‘The Den’ Self contained one bedroom annexe.
Guest house rentals with a washing machine and dryer

Daily Red Kite Feed & Pool - Countryside Apartment

Walk to West Wittering Beach | Pass The Keys

Modern Garden Room under 5 min walk to beach

Funtington village B and B - Cartbarn Sleeps 5

The Highland Cow - New Forest Tranquility

Lovely annex - a home away from home

Beautiful studio with direct access to New Forest

Delightful 2 bedroom annex on beachside road.
Quick stats about guest house rentals in Winchester
Total rentals
190 properties
Nightly prices starting at
$52 SGD before taxes and fees
Total number of reviews
11K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
70 properties have a dedicated workspace
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