Guesthouse vacation rentals in Winchester

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Top-rated guesthouse rentals in Winchester

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Guest favorite
Guesthouse in Hampshire
4.94 out of 5 average rating, 116 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 favorite
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 favorite
Guesthouse in Bramdean
4.99 out of 5 average rating, 127 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 favorite
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!

Top guest favorite
Guesthouse in Waltham Chase
4.96 out of 5 average rating, 135 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 favorite
Guesthouse in Winchester
4.97 out of 5 average rating, 537 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 favorite
Guesthouse in Bitterne Park
4.94 out of 5 average rating, 205 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 favorite
Guesthouse in Hampshire
4.99 out of 5 average rating, 103 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.

Top guest favorite
Guesthouse in Swarraton
4.99 out of 5 average rating, 127 reviews

Peaceful Studio Escape & Hot Tub under the stars

Come and enjoy the beautiful Hampshire countryside with a relaxing getaway with us in the Studio@Ashton Lodge. A light filled contemporary studio built in the gardens of our architect designed eco home. The perfect all season getaway! Enjoy the hot tub under the stars, take a walk through the woods at Micheldever, read a book on your sunbed, roast marshmallows on the fire pit, enjoy a meal at the Woolpack Inn. The studio is the perfect place to relax and unwind.

Top guest favorite
Guesthouse in Colden Common
4.99 out of 5 average rating, 121 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 favorite
Guesthouse in bugmore hill
4.93 out of 5 average rating, 165 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 favorite
Guesthouse in Sutton Scotney
4.99 out of 5 average rating, 242 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 guesthouse rentals

Quick stats about guesthouse rentals in Winchester

  • Total rentals

    190 properties

  • Nightly prices starting at

    ﺩ.ﺇ147 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

Destinations to explore

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  4. Hampshire
  5. Winchester
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