
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.

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.

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.

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.

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.

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.

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.

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 !!

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.

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.

“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.

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.

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
Pet-friendly house rentals

Lovely 2 bedroom home

The Old Stables, Derrydown Farm

Charming cottage less than 5 minutes from the sea

Rose Cottage, 4 bedrooms, parking 3 cars, garden

Cosy New Forest Farmhouse

Delightful 1 Bed Lodge In South Downs Village

Beautiful family house sleeps 9-10 5* reviews

Unique Penthouse in heart of Petworth, South Downs
Pet-friendly home rentals with a pool

Daily Red Kite Feed & Pool - Countryside Apartment

Shepherd's Hut (wood-fired hot tub/sauna optional)

Luxurious Lodge on Lake at Chichester with Hot Tub

Piilopirtti - a traditional Finnish log cabin

A holiday home in New Forest with pool & hot tub

‘Stag Cottage’ New Forest Romantic Hideaway

Grayswood Cowshed in stunning Grounds

5* waterside luxury boathouse - pool & log-burner
Private, pet-friendly home rentals

Coach House in the heart of the test valley

Honeysuckle Cottage - East Meon

Galley Hill Garden Studio

Arle Hut, riverside luxury on Vineyard estate

Ultra luxury, newly refurbished country retreat

Cosy Sussex Cottage. South Downs National Park

Cozy 2-Bed Apartment with Parking in Wickham

Colindale Cottage, Nether Wallop
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $406 CAD | $397 CAD | $431 CAD | $431 CAD | $415 CAD | $382 CAD | $376 CAD | $470 CAD | $385 CAD | $427 CAD | $411 CAD | $464 CAD |
| Avg. temp | 5 °C | 5 °C | 7 °C | 9 °C | 12 °C | 15 °C | 17 °C | 17 °C | 15 °C | 11 °C | 8 °C | 5 °C |
Destinations to explore
- Family-friendly rentals Winchester
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- New Forest National Park
- Bournemouth Beach
- West Wittering Beach
- Paultons Park Home of Peppa Pig World
- Goodwood Motor Circuit
- Longleat Safari Park
- University of Oxford
- South Downs National Park
- Thorpe Park Resort
- Chessington World of Adventures Resort
- Stonehenge
- LEGOLAND® Windsor Resort
- Southbourne Beach
- Windsor Castle
- Boscombe Beach
- Lower Mill Estate
- Hampton Court Palace
- Bracklesham Bay
- Mudeford Quay
- Highclere Castle
- Goodwood Racecourse
- Winchester Cathedral
- Ascot Racecourse
- The Tank Museum





