Pet-friendly vacation rentals in Winchester

Find and book unique pet-friendly homes on Airbnb

Quick stats about vacation rentals that are pet-friendly in Winchester

  • Total vacation rentals

    Explore 80 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at $28 CAD per night before taxes and fees

  • Verified guest reviews

    Over 2,670 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    80 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!

Top-rated pet-friendly home rentals in Winchester

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Guest favourite
A dark-stained tiny house is nestled in an expansive green field, overlooking the scenic South Downs National Park. Solar panels are visible on the roof, while the surrounding landscape features rolling hills and a bright blue sky filled with fluffy white clouds.
Tiny homes in Froxfield
4.84 out of 5 average rating, 152 reviews

Romantic OffGrid Cabin | Stargazing & Valley Views

Featured in The Guardian and The Times Top 10 UK Off-Grid Stays. Wake to sunrise over the South Downs in this secluded hilltop off-grid cabin overlooking the whole of the South Downs National park. Experience total serenity under star-filled skies with the warmth of a wood-burning stove enhancing the peaceful ambiance. Our off-grid cabin offers tranquility whilst still being close to cosy pubs, historic towns and scenic walks. Dog Friendly. It’s the perfect place to disconnect and recharge.

Guest favourite
Three cabins are arranged in a peaceful setting surrounded by greenery. A stone pathway leads to the front of the cabins, marked by wooden posts. Large windows provide views of the exterior landscape, creating a harmonious connection with nature.
Barn in Durley
4.97 out of 5 average rating, 408 reviews

Nettlebed Farm Holiday Lets, Barn1 of 3

* From £124 p/n +Airbnb charges Beautiful oak barn set in traditional english countryside. Placed with own access within 15 acres of private woodland and grazing land, away from the main road for peace and tranquility. Guests are able to have privacy for relaxation and enjoy views of horses grazing and the comings and goings of the British wildlife. Just 4 minute drive to the market town of Bishops Waltham or you can join and follow the infamous Pilgrims Trail and walk there in just 30 minutes.

Superhost
Home in Owslebury
4.86 out of 5 average rating, 295 reviews

The Joinery, Owslebury, Winchester

The Joinery is on the edge of Owslebury, a picturesque village just south of Winchester. It is light and airy and offers 4 bedrooms on ground floor level, two with ensuite shower and a family bathroom. Upstairs is a large open plan area with kitchen, dining table and sofas for relaxing and enjoying the views of the surrounding countryside.There is also a snug room with TV. There are steps down to the main entrance so not suitable for people with mobility issues. The garden area is not enclosed.

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, 158 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 favourite
A riverside log cabin is nestled among trees, featuring a spacious deck and seating area overlooking the water. Lush greenery surrounds the outdoor space, creating a natural setting that invites relaxation. The cabin’s wooden structure blends harmoniously with its peaceful environment.
Cabin in Reading
4.98 out of 5 average rating, 456 reviews

Riverside Log Cabin+Luxury Hot Tub Spa+Copper bath

Charming, riverside log cabin on the bank of the Kennett, overlooking a nature reserve. Privately located in my back garden there is a large open plan room with 2 double sofa beds, sleeping 4, a slate bed pool table & Hi Fi system. There's a luxury en suite bathroom with copper bathtub, shower, basin & WC. There are basic kitchen facilities with kettle, toaster, double hot plate, microwave & grill, sink & refrigerator/freezer. A veranda with 2 bbq's & seats plus lower deck overlook the river.

Top guest favourite
The open living area features a vaulted wooden ceiling with pendant lighting and a modern fireplace. Comfortable seating includes two sofas and decorative cushions. Artwork is displayed along the walls, and a television is mounted above the fireplace. Light floods in through large glass doors leading to the outdoor space.
Home in Salisbury
4.94 out of 5 average rating, 170 reviews

The Summer House

The Summer House is a recently converted guest house, self contained with fully equipped kitchen , beautifully fitted bathroom ,double bed on the galleried mezzanine level ,accessed by ladder stairs with vaulted ceiling creating a loft style. It is fully heated ,has wi-fi , streamed TV, and ceiling speakers for streaming music. The space is modern,bright ,yet cosy. Outdoors it sits at the top of 14 acres of grounds over looking the main house. There is a private entrance and parking on site.

Top guest favourite
A charming wooden annexe is nestled within a lush green garden, surrounded by manicured bushes. The building features a light-colored door and window shutters, adding to the rustic aesthetic. A small patio area with seating is visible, inviting outdoor relaxation.
Bungalow in Hampshire
4.94 out of 5 average rating, 145 reviews

The Annexe - Unique and Tranquil Getaway.

Take it easy at this unique and tranquil getaway, complete with its own private tennis court, should you wish to use it. In addition there is also a very large garden area to the front of the Annexe for you to enjoy. A private secure gated entrance with plenty of parking space is also provided. Two electric remote control Vellux windows complete with blinds also provide plenty of fresh air and light into your new home. A private patio area with seating and gas BBQ is also provided. Enjoy !!

Top guest favourite
An inviting living area features a curved wooden ceiling and large glass doors that open to a deck. Two reclining chairs are positioned on the outdoor space, complemented by shelves displaying books and decorative items. A round rug adds a cozy touch to the floor.
Cabin in Droxford
5 out of 5 average rating, 153 reviews

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.

Top guest favourite
The curved structure of The Farley Hangar is set amidst open fields, flanked by a solitary tree providing shade. A clear blue sky enhances the sense of tranquility, while the landscape offers a peaceful rural atmosphere.
Hut in Braishfield
4.99 out of 5 average rating, 400 reviews

The Hangar - countryside views, seclusion & peace.

The Farley Hangar is a peaceful space with far reaching views of Hampshire's woodlands and the Isle of Wight. Located on our family farm and private airstrip in the Test Valley. Winchester, Romsey and Stockbridge are just 20 mins away. On the doorstep of numerous cycle routes and footpaths including the Claredon Way (Sals-Win). King size bed & full-size bath with rain shower. From your private deck with log burner you will see various wildlife species and watch the stars at night.

Guest favourite
The image captures a standalone cabin nestled among trees, surrounded by greenery. A spacious gravel area in front features seating and an open-fronted shed. Steps lead up to the cabin, highlighting its private and tranquil setting within the landscape.
Tiny homes in Winchester
4.96 out of 5 average rating, 241 reviews

“The Hay Wagon " Large Unique Space

"The Hay Wagon." Bespoke Large Cabin Style living space. Tucked away and Private. Wonderful views of fields and far reaching landscape. Named after the "John Deere" HayTrailer it was built on. This extra large ‘Hay Wagon' which stands alone, nestles under the tree line with spectacular landscape views. Added in the grounds is a spacious open fronted shed which enhances your entertaining space and includes an outside rainfall hot shower, seating, coffee table and BBQ.

Top guest favourite
The Watch House is viewed from a garden path lined with blooming flowers, leading down to the beach. The white exterior of the cottage is highlighted against a clear blue sky, while the tide is low, revealing a sandy shore.
Home in Lepe
4.98 out of 5 average rating, 146 reviews

Iconic Beach Front Stay | The Watch House, Lepe

A standout seafront landmark on Lepe Beach, The Watch House is a lovingly restored former lifeboat and coastguard station, once used to combat smuggling across the Solent. With original features, a modern kitchen, wood burner, cosy window seat over the water, and views to the Isle of Wight, it’s a guest favourite—“an iconic beachfront stay” and “perfect relaxing getaway.” Pet-friendly with parking for two, perfect for families, couples, or friends.

Top guest favourite
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
4.98 out of 5 average rating, 290 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.

Popular amenities for Winchester pet-friendly home rentals

When is the best time to visit Winchester?

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