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Cottage vacation rentals in City of Winchester

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Top-rated cottage rentals in City of Winchester

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Cottage in Shawford

4.83 out of 5 average rating, 127 reviews

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.

Cottage in Droxford

4.92 out of 5 average rating, 134 reviews

Gorgeous Country Escape 5 Bedroom House & Annex

Family run, our pretty 5 bedroom detached house & separate annexe set in a rural location surrounded by the idyllic Meon Valley & South Downs Park The large garden is a haven, providing a perfect setting for alfresco dining with friends & family. With no direct neighbours you'll feel like you have the countryside all to yourselves Many beautiful cities on our doorstep, including Winchester, Chichester, Petersfield & Southsea Pool table • table football • X Box • Wii We welcome your dog 🐶

Cottage in East Hampshire District

4.87 out of 5 average rating, 200 reviews

Homely Country Cottage -South Downs national park

A spacious cosy cottage nestled into the foothills of Steep hangars with stunning views from the fields and woodland around the cottage. The main living area is a light and airy space on one floor with underfloor heating throughout. Fully equipped modern kitchen and bathroom with shower and bath. 2 spacious bedrooms with double beds. Fold up bed and cot also available. Local pub is a five minute walk up quiet country lane. There is a small safely enclosed back terrace and front garden.

Cottage in Bishop's Waltham

4.98 out of 5 average rating, 142 reviews

Beautiful garden house, edge of town & South Downs

Beautiful self-contained lodge in the glorious garden of a Georgian Country House. Five minutes walk to the small market town of Bishops Waltham, with shops, restaurants and pubs. Surrounded by stunning countryside, on the edge of the South Downs, with wonderful walks from the house. Open plan kitchen-dining area & lounge, 2 bedrooms and a bathroom upstairs plus separate downstairs shower room. Sunny patio area with table and chairs & Weber bbq, perfect for watching the sun go down.

Cottage in Hampshire

4.97 out of 5 average rating, 291 reviews

Colindale Cottage, Nether Wallop

Located between the historic cities of Winchester and Salisbury ,Colindale Cottage is an ideal base for exploring the Test Valley and beyond. Stonehenge, Highclere Castle and the New Forest are close by. The coast is approx and hour away. Dogs are welcome. Nether Wallop is a pretty village in the heart of the Test Valley close to the small town of Stockbridge with its independent shops and eateries. Nether Wallop featured in the Miss Marple series starring Joan Hickson.

Cottage in East Meon

4.98 out of 5 average rating, 110 reviews

Quaint Cosy Cottage in East Meon

Quaint Cosy Cottage in East Meon with access to Pubs, Shops, Historic Church and lots of country walks and access to South Downs National Park. It has public transport to both Petersfield and Winchester. This cottage benefits from 2 bedrooms, downstairs shower room/ toilet, kitchen and lounge with wood burning stove. With a view to a stream to the front and beautiful countryside to the rear. It has off road parking, lockable storage for bikes, small paved cottage garden.

Cottage in Winchester

4.82 out of 5 average rating, 273 reviews

Beggar's Lane Cottage-3 beds in Central Winchester

Beggar's Lane cottage is Grade II listed and built circa 1720 and retaining many original features. Two similar sized bedrooms with great views of Winchester Cathedral and a downstairs bathroom. There is a small courtyard back garden. The WiFi is fast. There will be fresh towels, dressing gowns, tea and coffee for you on your arrival. A short walk to the City centre, with it's many bars, shops, restaurants and other attractions. Located in an elevated and quiet street.

Cottage in Hambledon

4.94 out of 5 average rating, 192 reviews

Private cottage in a quiet countryside location.

Nestled in a peaceful South Downs hamlet, Courtyard Cottage is perfectly situated for a leisurely or active break in the country with easy access to the coast. The area is popular with walkers and cyclists due to the many footpaths and country lanes in the vicinity. There are also plenty of family attractions and sightseeing opportunities in the area. Guest will enjoy the privacy of the cottage with its own secluded courtyard garden. We are dog friendly!

Cottage in Sutton Scotney

4.89 out of 5 average rating, 445 reviews

Chic country cottage, hot tub & wood burning stove

Also please check out our newly refurbished nnexe on this site which we have just listed & still has September availability! This cottage is situated on our private country estate consisting of 7.5 acres. We live in the main house and we have two holiday lets on the estate (1) this cottage; and (2) our recently refurbished annexe! You will have sole use of the cottage and private hot-tub during your stay.

Cottage in Winchester

4.98 out of 5 average rating, 109 reviews

The Cottage in Compton

Come and enjoy a stay in The Cottage, located in the grounds of our 17th Century converted Barn. Enjoy a unique location on the edge of Winchester with direct access to the countryside. The Cottage has been recently extended and refurbished with everything you will need to make your stay enjoyable. A perfect place for a break to explore all the wonderful things that Winchester has to offer!

Cottage in Swanmore

4.84 out of 5 average rating, 128 reviews

Village Location/Comfortable 2 bed house from £90

Welsh Cottage is located in the centre of Swanmore with ample parking & green space around the village. The house is perfect for both weekend breaks & longer stays with 3 local pubs, shop & butchers within walking distance. Swanmore is within 25 minutes of Winchester, Portsmouth & Southampton with great tourist sites, eating & shopping to be had in all.

Cottage in Hampshire

4.97 out of 5 average rating, 178 reviews

Self-contained Lodge, Stockbridge

The Lodge has been newly renovated, giving 24sqm of self-contained studio style accommodation, with modern fitted kitchen and bathroom facilities. Located on the ever popular Stockbridge High Street with it's host of shops, pubs and restaurants, it also sits in the heart of the Test Valley with endless opportunities for those who love the outdoors.

Vacation rentals for every style

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Popular amenities for City of Winchester cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Cottage in Collingbourne Ducis

4.89 out of 5 average rating, 611 reviews

Cosy little country cottage with luxury hot tub

Cottage in Burley

4.9 out of 5 average rating, 179 reviews

‘Stag Cottage’ New Forest Romantic Hideaway

Cottage in Frogham

4.98 out of 5 average rating, 174 reviews

Luxury New Forest Cottage, with hot tub & log fire

Cottage in Hampshire

4.98 out of 5 average rating, 205 reviews

Wisteria Lodge, a self-contained unit with spa

Cottage in Godshill

4.98 out of 5 average rating, 163 reviews

Cottage with Covered Hot Tub Godshill New Forest

Cottage in Wherwell

4.93 out of 5 average rating, 236 reviews

Cottage in beautiful Hampshire village

Cottage in Hampshire

4.98 out of 5 average rating, 632 reviews

Detached and romantic cottage with hot tub.

Cottage in Baughurst

4.96 out of 5 average rating, 335 reviews

Luxury rural thatched cottage with cedar hot tub.

Pet-friendly cottage rentals

Cottage in Hampshire

4.99 out of 5 average rating, 176 reviews

Adventure Prospect - Historic Waterfront Cottage

Cottage in Hampshire

4.89 out of 5 average rating, 270 reviews

Thatched cottage, Wherwell, Test Valley Hampshire

Cottage in Plaitford

4.96 out of 5 average rating, 269 reviews

Manor Farm Cottage

Cottage in West Sussex

4.96 out of 5 average rating, 210 reviews

Elm Cottage, Goodwood Studio

Cottage in Pikeshill

4.97 out of 5 average rating, 261 reviews

Bramblings, New Forest cottage by the green

Cottage in West Sussex

4.82 out of 5 average rating, 398 reviews

Quintessential South Downs Cottage

Cottage in Brook

4.96 out of 5 average rating, 104 reviews

Gardeners cottage-pet friendly,New forest bolthole

Cottage in Ibworth

4.95 out of 5 average rating, 166 reviews

Self contained, rural cottage, 2 double bedrooms

Private cottage rentals

Cottage in Pikeshill

4.93 out of 5 average rating, 228 reviews

Hawthorns Cottage, in the heart of the New Forest.

Cottage in Ashford Hill

4.93 out of 5 average rating, 276 reviews

Thatched Grade ll property in Ashford Hill

Cottage in Isle of Wight

5 out of 5 average rating, 129 reviews

Pussy Mouse Rew, Idyllic Rural Cottage in 6 Acres

Cottage in Hampshire

4.97 out of 5 average rating, 112 reviews

Romantic cottage set in walled garden, New Forest

Cottage in Hampshire

4.96 out of 5 average rating, 187 reviews

Lyndhurst - A New Forest Gem with Garden

Cottage in West Sussex

4.9 out of 5 average rating, 100 reviews

The Coachman's Cottage

Cottage in Woodfalls

4.96 out of 5 average rating, 119 reviews

Farm Cottage on 9 acre Equestrian Small Holding.

Cottage in Walberton

4.99 out of 5 average rating, 174 reviews

Charming and elegant Victorian cottage

Quick stats about cottage rentals in City of Winchester

Total rentals
110 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
5.8K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
70 properties have a dedicated workspace

Destinations to explore