
Bed and breakfast vacation rentals in Winchester
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Top-rated bed and breakfast rentals in Winchester
Guests agree: these bed and breakfast rentals are highly rated for location, cleanliness, and more.

Oak House Barn near Chichester and Goodwood.
Overlooking The South Downs on the South Cycle Route ,in close proximity to Bosham, Chichester, and the sandy beaches of The Witterings is the annex to Oak House. On offer is a converted barn, containing 2 double bedrooms bathroom sitting room and fully equipped kitchen with self service breakfast included. Please be advised that the staircase is quite steep but there is a banister and stair gate. if required. Guests can see the animals in fields the goats live off the end of the small garden

The Piggery, Henley Hill
The Piggery is a beautiful self- contained, detached converted Piggery set in landscaped gardens as part of Verdley Edge and nestled between Cowdray woodland and the stunning South Downs. With walks from the doorstep and an award winning country pub ‘The Duke of Cumberland’ in walking distance, this is perfect retreat from busy lives. After 6 years superhosting over 500 guests The Piggery has just received a full renovation for 2024 and is looking extra lovely, we can’t wait to welcome you.

Rural Retreat. Comfort, style, views and garden.
Guest suite in wing of oak framed cottage. Situated in farmland between 2 picturesque villages, Old Basing and Newnham . Charming sitting room with log burner Spacious garden and terrace with covered verandah and furniture Simple DIY breakfast provided Private entrance King bed Great base for exploring country gardens and houses of Hampshire. Convenient for London, Winchester, Farnham, Windsor, Highclere Please note the location, vehicle required - 35 min walk to village and shops 2.5 miles +

Spacious Farmhouse Cowes perfect for Autumn breaks
Somerton Farm Cowes, wonderful spacious family farmhouse set in the countryside. Short walk to Cowes - Autumn break. Stunning views of countryside and river Medina near Northwood. Walking, cycling and wildlife (donkeys). SK double, King double/en-suite shower, 2 twin bedrooms and a family bathroom with bath(no shower). Large kitchen, dining room seats 8, sitting room with Smart TV also a family playroom. Dogs welcome. Parking .Ferry discount. FRI/MON arr/dep*Weekly Fri/Fri in school hols.

Swanage Luxury one bedroom private studio
You’ll love the stylish decor of this charming studio in Swanage. The Studio is a detached space with a kitchenette and an en-suite shower room. There is also an outside space to sit and relax. Parking on site. Studio is independently accessed so guests are free to come and go as they please. Located on a quiet residential road and just a 5/10 minute walk down hill to the beach, shops, restaurants, and pubs. Continental breakfast is delivered to your door 8.30am. Checkin 3pm checkout 10am.

Luxury house close to beach
Earnley Gate is a beautiful house and short distance to the Beach and Medmerry nature reserve. Very conveniently located about 5 miles south of Chichester as well as the renowned Goodwood Estate. Located down a quiet street with a large secured garden, the house is a generous size with bright and airy rooms. The kitchen is high spec and has everything needed for easy self catering. With a comfortable lounge and separate formal dining room, you can enjoy relaxed luxury for up to 6 people.

Oak Framed Barn with Tennis Court
A stylish secluded, two storey, oak framed barn with tennis court, 4 miles from Winchester. Homely space with two bedrooms plus a sofa bed (upon request) and ground floor open plan living area. Super fast WiFi. The Barn adjoins the Watercress Way and stands separately in the grounds with views over open Hampshire fields. Nearest neighbour c.1 mile away but there is loads to do in the area with an abundance of country pubs, one or two within walking distance and beaches within 50 minutes

Woodside Lodge ‘Acorn’ (& animal experiences)
Self-contained rural double room with en-suite shower room & own entrance via patio courtyard. Situated in paddocks & woodland in the heart of the beautiful tranquil New Forest. Breakfast baskets provided. Country pub within walking distance & miles of woodland and wildlife to explore. Optional exclusive VIP hands-on experiences suitable for all ages (£45 - bookable in advance/subject to availability) Explore miniature horses, stables, aviaries, owls, sheep and reptile house.

Salisbury Cathedral Close Log Cabin with En Suite
Photo from gates by log cabin leading to the Close & Cathedral.. En-suite log cabin in glorious situation with garden. Comfortable bed. Blackout blinds/curtain or sleep with doors open in Summer. Parking included. TV, WiFi, tea/coffee, microwave, fridge. Simple Breakfast or self catering. Near Cathedral, 5 mins walk to medieval city with Shops, market restaurants, entertainments. Stonehenge 20 minute drive or bus. Special price, 3 nights: £250.

Double room in a beautiful rural cottage
A quintessentially English country cottage tucked away down a lane surrounded by woods and fields and yet only a 15 minute drive from the heart of the beautiful city of Winchester, this is the perfect rural retreat to relax and explore the South Downs National Park. Please note the guest bed is a standard double size. Breakfast includes fresh fruit, local honey and eggs from the Hens if available as well as cereals, bread, teas, OJ and coffee.

Bedroom 2 in a country house close to Winchester
Bedroom 2 is part of a 6 Bed detached house in its own grounds on the outskirts of a Hampshire village famous for its timber framed black and white thatched properties. The house is surrounded by agricultural fields. The accommodation available is for up 6 people in 3 bedrooms in the house. Prices quoted are for one bedroom with Single or Double occupancy. If you wish to book the other bedrooms they are listed as Bedroom 1 and 3 on airBnb.2

The Chicken Shed
The` Chicken shed` is a cosy 1 bedroom annexe with en-suite shower room, on the courtyard of Highground Barn, which is a traditional Sussex flint barn originally built in 1760 and converted in 2004. The property sits at the end of a quiet country lane in Barnham village surrounded by fields of grazing horses, and is an ideal location to stay and relax. A stay at the `Chicken Shed` is sure to be a peaceful and relaxing time.
Popular amenities for Winchester bed and breakfast rentals
Family-friendly bed and breakfast rentals

Spacious room in quiet location close to station

Private ensuite double bedroom in Godalming

Plaegan House 【Back Cat】

Cosy flint cottage near Goodwood

Sunny twin/double room near Downs

Ideal base for exploring Dorset coast and country

April Cottage B & B, Swanage

30's style house in a quiet street
Bed and breakfast rentals with breakfast

3-bedroom cottage near Stonehenge

Beautiful double bedroom in tranquil setting.

Rectory w/ Stunning Views (Room 2)

Beautiful double room in house with own bathroom

IOW Seaside Superking/twin ensuite room

Cosy annex, private entrance, Beach & RSPB nearby

Hamilton House

Warm and friendly B&B King Room in Gosport
Bed and breakfast rentals with a patio

KingSize, Own Bathroom, Breakfast, Close to centre

Ensuite double room betwixt the forest and the sea

Private en-suite room in country House Room Only

Goodwood double room with ensuite

Luxury country retreat

Small Single BR NFLX/Workspace beside IKEA Reading

The Snug - en suite double room, own shower room

Peaceful room in a Victorian house
Quick stats about bed and breakfast rentals in Winchester

Total vacation rentals
Explore 40 vacation rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at G$8,367 GYD per night before taxes and fees

Verified guest reviews
Over 650 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 of Winchester vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winchester rentals

4.8 Average rating
Winchester stays are highly rated by guests—averaging 4.8 out of 5!
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 - Bed and breakfasts Hampshire
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- New Forest national park
 - Paultons Park Home of Peppa Pig World
 - Oxford University
 - Goodwood Motor Circuit
 - Stonehenge
 - Bournemouth Beach
 - Windsor Castle
 - Hampton Court Palace
 - Boscombe Beach
 - Chessington World of Adventures Resort
 - Winchester Cathedral
 - Highclere Castle
 - Kimmeridge Bay
 - Thorpe Park Resort
 - Twickenham Stadium
 - West Wittering Beach
 - Goodwood Racecourse
 - Highcliffe Beach
 - Southbourne Beach
 - Worthing Pier
 - The Tank Museum
 - Wentworth Golf Club
 - RHS Garden Wisley
 - Poole Quay