Cottage vacation rentals in Winchester

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Top-rated cottage rentals in Winchester

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Top guest favorite

A serene natural landscape showcases a tranquil pond surrounded by lush green foliage and tall grasses. Reflections of trees and cloudy skies are visible in the still water, enhancing the peaceful ambiance of the wooded area.

Cottage in Salisbury

4.99 out of 5 average rating, 107 reviews

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.

Top guest favorite

A cozy sitting room is featured, showcasing a comfortable armchair and a large coffee table adorned with various books and decorative items. A warm fire burns in the fireplace, and built-in shelving lines one wall, filled with a diverse selection of books.

Cottage in Warfield

4.98 out of 5 average rating, 272 reviews

Newly refurbished luxury 2 bedroom cottage

Luxury cottage at Hayley Green that accommodates up to 4 people. Newly refurbished in semi-rural setting. Full of character with all the amenities you need for a luxurious comfortable stay. The perfect relaxing getaway for couples, family and friends. The cottage is located 16 minutes to Windsor, 30 minutes to Henley on Thames, 11 minutes to Ascot, 9 minutes to Legoland, 6 minutes drive to Lapland Ascot.We are also close to Bracknell train station where you take a train to London under 1 hour.

Superhost

An open plan living, kitchen, and dining area is depicted, featuring a dining table with wooden chairs and a patterned tablecloth. The kitchen includes a stainless steel refrigerator, stove, and ample cabinetry. Soft seating is arranged in the living area, enhancing a comfortable environment.

Cottage in Shawford

4.83 out of 5 average rating, 136 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.

Top guest favorite

The exterior of the lodge is captured, featuring a brick facade with white-framed windows. A spacious lawn is visible in front, along with a small patio area equipped with outdoor seating and a table. Tall trees frame the background, enhancing the tranquil setting.

Cottage in Bishop's Waltham

4.98 out of 5 average rating, 150 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.

Top guest favorite

The exterior of Colindale Cottage is depicted, showcasing a two-story structure with a light-colored façade. A garden room with glass panels is visible, along with well-kept flowerbeds and a lush green lawn. A large tree provides shade in the tranquil outdoor space.

Cottage in Hampshire

4.97 out of 5 average rating, 317 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.

Top guest favorite

A spacious living area features a comfortable sofa and two armchairs, oriented towards arched glass doors that provide ample natural light. A coffee table sits in the center, with decorative items arranged neatly. The wooden floor and neutral walls create a welcoming atmosphere.

Cottage in West Sussex

4.99 out of 5 average rating, 171 reviews

Quiet location. Close to Coast, Downs & Goodwood

Situated in the grounds of our Victorian family home, the newly converted 'Garden Rooms' occupy a separate self-contained building, furnished to a high standard, and perfect for coupes wishing to enjoy walking, cycling & sailing in the South Downs National Park. The annex has its own driveway and self check-in is via a key box. The Garden Rooms are located in the pretty downland village of West Ashling. There are three local pubs & a restaurant, all within walking distance.

Top guest favorite

A quaint stone cottage is depicted against a clear blue sky, with a lush green hillside in the background. The structure features whitewashed walls, multiple chimneys, and a well-maintained hedge, creating a charming appearance near the water's edge.

Cottage in East Meon

4.97 out of 5 average rating, 132 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.

Guest favorite

The exterior of the property displays a charming wooden facade with large glass doors, allowing natural light to fill the living space. A neatly landscaped garden features lush greenery, stone pathways, and patio seating, creating an inviting outdoor environment.

Cottage in Pikeshill

4.97 out of 5 average rating, 302 reviews

Bramblings, New Forest cottage by the green

Bramblings is in a magical position, at the edge of Lyndhurst, on the green and just over the cattle grid. It is just a short walk in to Lyndhurst for restaurants, cafes and shopping and there are great walks and cycling direct from the house. Remember to keep the gate shut whenever you are coming and going as the ponies, donkeys and cows are free to meander just outside and they are always keen to help themselves to the greenery in the garden.

Top guest favorite

The image features a serene waterfront scene at dusk, with a pink and blue sky reflecting on the calm water. The weathered stone wall encloses a small harbor, while historic buildings are positioned nearby, contributing to the tranquil ambiance.

Cottage in Hampshire

4.99 out of 5 average rating, 206 reviews

Adventure Prospect - Historic Waterfront Cottage

Relax and enjoy your stay at this unique and tranquil getaway. 'Adventure Prospect' has recently been completely renovated and is steeped in military history. Formerly known as the "shifting house" it was first built in 1898-1899 to accommodate munitions workers changing into the special clothing that they wore when working on magazines. The cottage provides an ideal escape from everyday life and has direct access to the water.

Guest favorite

A stylish barn exterior showcases a mix of wooden and brick elements. French doors open to a bright interior with a bed visible inside. Two deck chairs are positioned on the terrace, and a chiminea stands to the side, all set against a landscaped garden.

Cottage in Privett

4.96 out of 5 average rating, 542 reviews

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!

Top guest favorite

The Cottage features a charming exterior with a textured roof and a modern patio area. Surrounded by greenery, a spacious seating arrangement is set on a stone surface, offering a tranquil spot for relaxation. Nearby structures exhibit a contemporary architectural style.

Cottage in Winchester

4.99 out of 5 average rating, 150 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!

Guest favorite

The exterior of the lodge features a charming wooden façade with distinctive double doors and a blue entrance door. Potted plants adorn the gravel pathway, adding greenery to the inviting atmosphere. A large tree provides shade in the background under a bright blue sky.

Cottage in Hampshire

4.97 out of 5 average rating, 202 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.