Guesthouse vacation rentals in Winchester

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Top-rated guesthouses in Winchester

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

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Guest favourite
A well-appointed room features a spacious bed with plush bedding. Light wood flooring complements the seating area with a circular table and two upholstered chairs. Skylights and decorative lamps provide soft lighting. A mirror adds depth, and a hairdryer is available on the wall.
Guesthouse in Hampshire
4.92 out of 5 average rating, 123 reviews

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.

Guest favourite
A bright and inviting kitchen area is shown, featuring modern appliances and wooden countertops. A dining table with patterned tablecloth and several wooden chairs is visible. Shelving displays kitchen essentials, and light filters through skylights, illuminating the space.
Guesthouse in Hampshire
4.93 out of 5 average rating, 235 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.

Top guest favourite
The bungalow is illuminated at night, showcasing its warm exterior lighting. A spacious terrace is visible, complete with a large umbrella, while decorative lights softly outline the railing. The inviting atmosphere highlights the building's rustic design and surrounding greenery.
Guesthouse in Bramdean
4.99 out of 5 average rating, 130 reviews

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 favourite
A detached guest house is set within a spacious green lawn, surrounded by trees and neatly trimmed hedges. The building features a brown-tiled roof and an exterior painted in a light hue, with a window on the front wall reflecting the sky.
Guesthouse in Swarraton
4.93 out of 5 average rating, 105 reviews

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!

Superhost
A bright sleeping area features a striped bedding set on a single bed with built-in storage beneath. Light enters through two large glass doors that open to the outside. A small table and chair are positioned nearby, complemented by a decorative plant in the corner.
Guesthouse in Southampton
4.78 out of 5 average rating, 540 reviews

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

Top guest favourite
A spacious living area is showcased, featuring a comfortable sectional sofa and two modern chairs. A round wooden coffee table is placed on a patterned rug. Soft lighting illuminates the room, highlighting a minimalistic design with decorative elements and a kitchenette visible in the background.
Guesthouse in Waltham Chase
4.96 out of 5 average rating, 139 reviews

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.

Top guest favourite
A charming brick and flint building is surrounded by neatly trimmed bushes and a well-maintained garden. Two wooden chairs and a small table are set outside, inviting guests to enjoy the tranquil rural setting under clear skies.
Guesthouse in Winchester
4.97 out of 5 average rating, 541 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!

Top guest favourite
A lounge area features a large corner sofa in soft gray with a pink cushion, providing a cozy seating option. A wooden mirror and a small television are positioned over a simple fireplace. A potted plant and children's toys are visible, enhancing the space's functionality.
Guesthouse in Bitterne Park
4.94 out of 5 average rating, 208 reviews

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 🌳🦆

Top guest favourite
A spacious bedroom features a comfortable kingsize bed adorned with decorative pillows. On each side of the bed, bedside lamps provide soft illumination. Framed artwork is displayed on the wall above, while a vintage mirror enhances the light and openness of the space.
Guesthouse in Hampshire
4.99 out of 5 average rating, 105 reviews

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.

Guest favourite
A spacious bedroom features a comfortable king-sized bed with white linens and decorative pillows. Two bedside tables with lamps are positioned on either side. Large windows invite natural light, and the walls are finished in a soft neutral tone, surrounded by a green carpet.
Guesthouse in Colden Common
4.98 out of 5 average rating, 123 reviews

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.

Top guest favourite
A light-filled living area showcases a comfortable sofa draped with a blue blanket and decorative cushions. A small table sits beside the sofa on natural woven flooring. The bedroom is visible through sliding doors, featuring a bed with colorful linens and a window that allows for ample natural light.
Guesthouse in bugmore hill
4.93 out of 5 average rating, 169 reviews

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.

Top guest favourite
This charming brick studio features a sloped roof and large glass doors that invite natural light. Surrounded by greenery, it is set on a gravel pathway with potted plants, creating a serene entrance to the retreat.
Guesthouse in Sutton Scotney
4.99 out of 5 average rating, 245 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.

Popular amenities for Winchester guesthouses

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Avg. price$137 CAD$140 CAD$152 CAD$157 CAD$164 CAD$152 CAD$143 CAD$145 CAD$150 CAD$153 CAD$147 CAD$150 CAD
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Quick stats about guesthouse rentals in Winchester

  • Total vacation rentals

    Explore 190 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at $56 CAD per night before taxes and fees

  • Verified guest reviews

    Over 10,590 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wifi availability

    180 of Winchester vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winchester rentals

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