
Cottage vacation rentals in Winchester
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Top-rated cottage rentals in Winchester
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80 acre Wood, Dutchtub, Lake, Treehouse & Zip-line
Escape to a private 80-acre woodland, just 10-15 minutes from the historic, and picturesque, city of Salisbury. Enjoy tranquil trekking trails, or relax by the secluded lake. Glide through the trees, from the fun kids treehouse, on our 100 ft zip-line, or wind down by immersing yourself in nature with a good soak in our wood-fired Dutch tub. We believe our guest cottage offers the perfect balance of natural and peaceful comfort; ideal for romantic escapes, family adventures, or digital detoxes.

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.

Beautiful Winterberry Barn ,With Hot tub
WinterBerry Barn is a gorgeous 1 bedroom cottage with everything you could possibly need for a cosy country getaway. It has a beautiful wood fired hot tub .Every aspect of the property is finished to the highest standard. Oak finish throughout with raw natural beams flowing through the property to really give it that warm country feel. Close to all the wonderful local amenities such as the beautiful market town of romsey only a 5 minute drive! Also the beautiful historic city of Winchester.

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.

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.

The Coach House with walled garden
Our converted coach house offers a cosy corner in the busy village of Downton from which to visit the historic cathedral city of Salisbury and the open spaces of the New Forest. Parts of the property date back to 1475 with links to the Bishops of Winchester. There is plenty on offer in and around the village, with local shops, gardens, pubs, walks and bicycle rides along the River Avon. Bournemouth beaches are not far away. We welcome dogs (please see info regarding fee).

Entire Country Cottage in Hampshire's Test Valley
This stunning country cottage is located in the heart of the Test Valley with its own patio and garden looking out to the fields behind. It is nestled in a lovely rural setting, with beautiful walks from the house, pubs and village amenities within walking distance. The cottage has luxury fittings, a wood burner and provides a haven for couples whatever age to getaway in an idyllic part of rural England. We are happy to host one well behaved pet.

Romantic cottage set in walled garden, New Forest
Situated in the grounds of an impressive country house, Butler's Rest is a stylishly renovated, quirky 19th Century cottage. Perfect for a romantic escape. In an unspoiled part of the New Forest, deer roam through the gardens, a short walk from three wonderful pubs and the open forest itself. It's a great setting from which to explore, although with a well equipped kitchen and cosy woodburner, you may not venture anywhere!

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!

Country Cottage near Winchester, Hampshire
Tenacre Cottage is a cosy and quirky semi-detached cottage located in the outskirts of the rural village of Owslebury. Just a 5-mile drive from the medieval city of Winchester, Tenacre Cottage is situated in a prime location, perfect for a rural getaway or business stay. Secluded from the busy bustle of the city, yet a swift 10-minute drive, Tenacre Cottage is surrounded by acres of fields and beautiful views.

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!

Cosy country cottage with chalk stream charm
A beautifully renovated and charming lodge on the river Dever, ten minutes drive north of the historic city of Winchester. The Fisherman's Lodge is a beautiful self contained country escape with the added benefits of its own little island and brilliant views of the charming river Dever and the wildlife that lives along its banks.
Popular amenities for Winchester cottage rentals
Cottage rentals with a hot tub

Cosy little country cottage with luxury hot tub

Holiday cottage With hot tub

Blashford Manor Farm - The New Forest Cottage

The Old Piggery, East Boldre, New Forest

Superb cottage edge of new forest near paultons

Luxury New Forest Cottage, with hot tub & log fire

Wisteria Lodge, a self-contained unit with spa

Cottage with Covered Hot Tub Godshill New Forest
Pet-friendly cottage rentals

Stylish Hideaway with an amazing woodland view

Chicory Cottage: Beautiful Cotswolds Home + EV ch.

Duck Cottage self catering cottage

The Forge

Modern 2 bed detached Cottage near Salisbury

New Forest retreat, cosy & pretty, 4 guests

Forest’s Edge - Ashurst

Self contained, rural cottage, 2 double bedrooms
Private cottage rentals

Watch the deer from your cosy barn near Goodwood

Beautiful oak barn in peaceful countryside setting

The Old School House, Ascot, Berkshire

The Billiard Room, The Green, Biddestone, SN14 7DG

Quiet location. Close to Coast, Downs & Goodwood

Stride cottage 4 nights minimum stay.

Self contained 1 bedroom annexe with free parking

Pussy Mouse Rew, Idyllic Rural Cottage in 6 Acres
Quick stats about cottage rentals in Winchester
Total vacation rentals
Explore 10 vacation rentals in Winchester
Nightly prices starting at
Winchester vacation rentals start at $140 CAD per night before taxes and fees
Verified guest reviews
Over 560 verified reviews to help you choose
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 of Winchester vacation rentals include wifi 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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- New Forest national park
- Paultons Park Home of Peppa Pig World
- Oxford University
- Bournemouth Beach
- Goodwood Motor Circuit
- Stonehenge
- Windsor Castle
- Boscombe Beach
- Hampton Court Palace
- Lower Mill Estate
- Chessington World of Adventures Resort
- Winchester Cathedral
- Highclere Castle
- Kimmeridge Bay
- Thorpe Park Resort
- West Wittering Beach
- Goodwood Racecourse
- Southbourne Beach
- Highcliffe Beach
- Arundel Castle
- The Tank Museum
- Wentworth Golf Club
- Worthing Pier
- RHS Garden Wisley