
Cottage holiday 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.

Idyllic Cottage in the heart of The South Downs
The Old Bakery is a luxurious self-contained cottage set in the heart of the beautiful South Downs National Park. It has been voted one of the best Air B&Bs in the UK in 2021! Guests can enjoy beautiful walks directly from the cottage or visit local villages such as Haslemere, Midhurst, Petworth, Arundel, the South Coast (West Wittering) and Goodwood. You will be spoilt for choices with some excellent pubs and restaurants in the area with the fabulous Duke of Cumberland pub a short walk away.

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.

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!

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.
Popular amenities for cottage rentals in Winchester
Cottage rentals with a hot tub

Cosy little country cottage with luxury hot tub

Holiday cottage With hot tub

Adorable Detached 1 bedroom Annexe with hot tub

The Old Piggery, East Boldre, New Forest

Superb cottage edge of new forest near paultons

Wisteria Lodge, a self-contained unit with spa

Luxury New Forest Cottage, with hot tub & log fire

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

Beautiful, secluded, country cottage near to beach

Farthings - genuine Austen charm cottage & garden

Stylish Hideaway with an amazing woodland view

The Forge

Modern 2 bed detached Cottage near Salisbury

New Forest cottage by the green

New Forest retreat, cosy & pretty, 4 guests

Luxury Cottage near Stonehenge & Salisbury
Private cottage rentals

2 Tudor Cottage - Cosy period cottage, West Sussex

Gorgeous rural escape only 10 mins from Winchester

Cosy Victorian cottage set in a country park

Beautiful oak barn in peaceful countryside setting

Beautiful 16th Century thatched cottage

The Old School House, Ascot, Berkshire

Quiet location. Close to Coast, Downs & Goodwood

The Nestle House City Centre Luxury
Quick stats about cottage rentals in Winchester

Total holiday rentals
Explore 10 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $130 SGD 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 holiday 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
- Goodwood Motor Circuit
- Stonehenge
- Bournemouth Beach
- Windsor Castle
- Hampton Court Palace
- Boscombe Beach
- Lower Mill Estate
- Chessington World of Adventures Resort
- Winchester Cathedral
- Highclere Castle
- 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




