
Guesthouse holiday rentals in Winchester
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Top-rated Guesthouses in Winchester
Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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.

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.

Cosy cabin with hot tub in peaceful location
Private and quaint location in Bitterne Village, which has a good selection of pubs and restaurants within walking distance or a short taxi ride. 5 min walk to local shops and supermarket. 5 min drive to the M27 motorway with onward access to the M3. 10 min drive to Southampton city centre, and the sea front/Ocean Village Marina. 5 min drive to the beautiful Hamble (River) with a great selection of pubs and restaurants along the river.

Self contained unit with easy links to motorway.
This is a fully furnished mobile home in the grounds of a detached cottage on the outskirts of Titchfield, which is half-way between Portsmouth and Southampton. There is space to park a car off the road. There is a local village centre and more shops at larger local centres in Fareham and Whiteley. There is no washing machine or dryer in the property but guests can use the facilities in the main house.

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
Family-Friendly guesthouses

Garden Annex in Haslemere

Beaufort Lodge - private lodge in tranquil setting

Seaside Cottage. Cosy Retreat.

Stylish self contained lodge near St Mary Bourne

New Forest garden chalet.

Lymington Annexe: own entrance, garden, parking

The Beehive- Beautiful garden room + breakfast

Private Lodge close to beaches and Goodwood
Guesthouses with a patio

Charming Bosham Garden Lodge | Pass The Keys

The Nook - Forest/Coastal Luxury Studio

The Courtyard Hideaway | Midhurst

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.

Delightful boathouse overlooking Fishery Creek.
Guest house rentals with a washing machine and dryer

Stunning oak-framed "Loft House"

Walk to West Wittering Beach | Pass The Keys

Funtington village B and B - Cartbarn Sleeps 5

Self-contained studio Wokingham

The Highland Cow - New Forest Tranquility

Lovely annex - a home away from home

Beautiful studio with direct access to New Forest

Countryside Garden Cabin
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $175 NZD | $178 NZD | $192 NZD | $200 NZD | $208 NZD | $192 NZD | $192 NZD | $214 NZD | $216 NZD | $185 NZD | $187 NZD | $191 NZD |
| Avg. temp | 5°C | 5°C | 7°C | 9°C | 12°C | 15°C | 17°C | 17°C | 15°C | 11°C | 8°C | 5°C |
Quick stats about guesthouse rentals in Winchester

Total holiday rentals
Explore 190 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $71 NZD per night before taxes and fees

Verified guest reviews
Over 10,590 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
180 of Winchester holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Winchester rentals
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- New Forest national park
- Goodwood Motor Circuit
- Paultons Park Home of Peppa Pig World
- Oxford University
- Stonehenge
- Windsor Castle
- Hampton Court Palace
- Bournemouth Beach
- Boscombe Beach
- Winchester Cathedral
- Highclere Castle
- Chessington World of Adventures Resort
- Twickenham Stadium
- Kimmeridge Bay
- Thorpe Park Resort
- West Wittering Beach
- Goodwood Racecourse
- Highcliffe Beach
- Southbourne Beach
- Worthing Pier
- The Tank Museum
- Wentworth Golf Club
- RHS Garden Wisley
- Poole Quay
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