
Vacation rentals with breakfast in Winchester
Find and book unique accommodations with breakfast on Airbnb
Quick stats about vacation rentals with breakfast included in Winchester

Total vacation rentals
Explore 20 vacation rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at $42 CAD per night before taxes and fees

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Over 2,030 verified reviews to help you choose

Wifi availability
20 of Winchester vacation rentals include wifi access

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

4.9 Average rating
Winchester stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated accommodations with breakfast in Winchester
Guests agree: these breakfast rentals are highly rated for location, cleanliness, and more.

The Nest
This charming 3-bed cottage with private parking and garden is situated in Shawford, near to the historic town of Winchester. Walks along the River Itchen, swimming, fishing and picnic spots are on your doorstep. Local pub in Shawford and pubs in nearby village of Twyford. Winchester is also accessible by foot ( 45 mins) or a short 5 minute train or bus away. London is an hour by train and other local attractions include Marwell Zoo, Peppa Pig World, South Coast, Portsmouth and New Forest.

The Pigsty
The Pigsty is Winchester's first luxury woodland hideaway, with beautiful views of Vale Farm. Less than 2.5 miles from the historic centre of Winchester, this peaceful retreat is perfect for those looking to visit the city, or escape for some peace. The Pigsty’s domed design with wooden interior has a roll top bath, cosy open plan living space and decking area to enjoy dinner with sunset views. Just a few minutes walk from the famous Clarendon Way, and a 30 minute walk to the city centre.

Woodrest Cabin, South Downs National Park
Your escape to Woodrest starts with a beautiful walk through ancient woodland to a private and secluded meadow. We have two hand built cabins each set in their own acre of meadow. On arrival you will be met with the most stunning views of the Meon Valley. This unique stay allows you to switch off and enjoy the benefits of being on a family run farm, which has footpaths and woodland for you to explore. The South Downs Way is a short hike away, which leads to a wonderful nature reserve.

"Bumble" The Shepherd's Hut
This traditionally inspired, hand-made Shepherds Hut is nestled inside a paddock in the leafy county of Hampshire. It offers a tranquil retreat in a home away from home setting with a cosy open plan living space championed by the log burning stove. Enjoy cooking your own English Breakfast - of which eggs are graciously supplied by our chickens -amongst views and visits of our 17 strong Alpaca herd. Please let us know if you'd like to meet and feed the Alpaca - they'd like to meet you!

Nature’s Nook Cosy Couples Woodland Cabin Hursley
Nature's Nook offers guests the perfect rural escape. You will be treated to spectacular views across the Winchester countryside and wildlife right outside your doorstep. Nature's Nook is perfectly located, nestled on the edge of a bluebell woodland with country walks just minutes away and the historical city of Winchester a short drive away. Curl up on the sofa with a book, sit outside by the fire pit, whilst enjoying a drink, or just relax and admire the stunning scenery!

Quiet self-contained 4 guest annexe close to town
Lovely two bedroom annexe on a peaceful residential road in Alton, located just a short walk from the local amenities of this pretty market town including a Triple fff brewery pub and premium supermarkets. On the edge of the South Downs National Park Alton is surrounded by beautiful countryside ideal for cycling and walking. The house has it's own private entrance, driveway parking and fast wifi, kitchen, restful living room, bright airy bedrooms and a stylish shower room.

Peaceful private annexe with far-reaching views
The first floor annexe is accessed via a covered external staircase. Home from home, cosy but spacious one bed (2 guests) accommodation with living space and kitchen. The balcony is perfect for morning coffee/evening drinks (weather allowing) with far reaching views over the Hampshire countryside. The annexe is adjacent to our home but is entirely private for guests' exclusive use. We will welcome you, and can answer any questions but we will also respect your privacy.

River Hamble Boutique Barn
Located 400m from the River Hamble in the small coastal village of Warsash in Hampshire. Perfect if you are studying at the Maritime College, are looking for a relaxing time near the water or as a base to explore further afield. The New Dairy has off road parking and easy access 24/7 Pubs, restaurants, takeaways and a Coop are within easy walking distance You will be welcomed with a complimentary basket that includes continental breakfast supplies.

Beautiful guest suite in Hampshire
Set in the grounds of a Grade II listed thatched cottage on the edge of Kings Worthy village, our annex is beautifully decorated and comfortable. With its own entrance and small private outdoor area, this property combines rural charm and handy local amenities (bus stop just outside to central Winchester and fantastic local pub just a two minute walk away). Tea and coffee are provided as well as breakfast cereals, bread/butter and fruit jams.

The Post Barn - Beautiful barn 10min to Winchester
A beautifully renovated 1000 sq ft barn, perfect for couples, friends or families, nestled at the heart of one of Hampshire's most picturesque villages, 10 mins from Winchester and 75 mins from Waterloo. Your hosts Lisa and Josh welcome you to The Post Barn, formerly the annexe of the village post office, now restored for those who wish to walk, run or cycle in the surrounding countryside...or enjoy all that Winchester has to offer.

The Barn @ North Lodge -Soho Farmhouse-esque Cabin
Inspired by Soho Farmhouse. A stylish converted barn set in the grounds of a Georgian Lodge within the South Downs National Park. Conveniently located close to the picturesque market towns of Alresford, Petersfield, Alton and historic Winchester, it is an ideal base to both explore Hampshire and kick back and relax in luxury. Take a look at the Barn on ‘Escape to the Country’ series 25, Episode 10 on iPlayer!

Luxury Studio with Hot Tub & Sauna
Welbeck Studio is a private, self contained luxury escape with the added benefits of your own private hot tub & sauna. Nestled in the little village of Nutbourne close to the pretty historic fishing villages of Emsworth and Bosham and the Roman City of Chichester. We are just a 10 min drive to Goodwood and 15 minutes to Historic Portsmouth and the beautiful award winning beaches of West Witterings.
Popular amenities for Winchester accommodations with breakfast
House rentals with breakfast

The Barn at Myrtle Cottage

Dibbens Townhouse

Luxury 5-Bed Beach House • Sea Views • Sleeps 10

Beautiful Self Contained Annex near Arundel.

Spacious one bedroom annex in Hampshire village

Pretty self contained cottage in private garden

Spacious Townhouse

Delightful Sunny House Close to the Village Square
Apartment rentals with breakfast

Super sunny studio with own terrace & parking

Stylish Barn in Rural Hampshire

Southsea Rooftops

Self contained studio flat in Henley on Thames

Spacious self-contained flat in Parkstone

Newly Refurbished Spacious Flat : Highclere

Southsea - Welcoming Seaside Apartment

Beautiful 1 BR flat 5 min walk to South Downs Way
Bed and breakfast rentals with breakfast

Swanage Luxury one bedroom private studio

The Chicken Shed

Salisbury Cathedral Close Log Cabin with En Suite

17th Century Town House in Central Winchester

The Garden House/Jane Austen Chawton inc breakfast

Double room in a pretty rural cottage

Large, sunny room in village house

Cosy flint cottage near Goodwood
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- New Forest National Park
- Bournemouth Beach
- West Wittering Beach
- Paultons Park Home of Peppa Pig World
- Goodwood Motor Circuit
- Longleat Safari Park
- University of Oxford
- South Downs National Park
- Thorpe Park Resort
- Chessington World of Adventures Resort
- Stonehenge
- LEGOLAND® Windsor Resort
- Southbourne Beach
- Windsor Castle
- Boscombe Beach
- Lower Mill Estate
- Hampton Court Palace
- Bracklesham Bay
- Mudeford Quay
- Highclere Castle
- Goodwood Racecourse
- Winchester Cathedral
- Ascot Racecourse
- The Tank Museum





