Waterfront holiday rentals in Winchester

Find and book unique waterfront rentals on Airbnb

Quick stats about waterfront rentals in Winchester

  • Total holiday rentals

    Explore 130 holiday rentals in Winchester

  • Nightly prices starting at

    Winchester holiday rentals start at $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 5,610 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    120 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!

Top-rated waterfront rentals in Winchester

Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

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Guest favourite
A wooden lodge is nestled among lush greenery, featuring a large deck with a wooden railing. The facade of the lodge includes large windows that allow natural light inside, complemented by a sloped roof. Outdoor seating is visible on the deck.
Farm stay in West Wellow
4.9 out of 5 average rating, 504 reviews

Pine Lodge - Headlands Farm

🌲 Pine Lodge — Lakeside Retreat for Families & Friends @headlandsfarmlakesidelodges @headlandsfarm ✨ Perfect for families of 4, couples , or mixed groups seeking a peaceful countryside escape. Step outside to your child-friendly lakeside decking right on the water’s edge. Enjoy breakfast at our onsite coffee shop ☕, discounted fishing 🎣, plus sauna & cold plunge, padel, and massage & beauty treatments 🧘‍♀️🎾💆‍♀️. Dog friendly, with self check-in 🧼 — 5 more lodges available on Airbnb 💌

Top guest favourite
Cabin in Old Alresford
4.99 out of 5 average rating, 119 reviews

Arle Hut, riverside luxury on Vineyard estate

A beautifully designed shepherd's hut on a working Hampshire farm, set on a private tributary of the River Arle — one of England's finest chalk streams. Ten minutes' walk from Alresford along the river path. Wake to birdsong and the gentle sound of running water in one of the most peaceful settings in Hampshire. King-size pocket sprung bed, fully equipped kitchen, powerful hot shower and a two-person outdoor bath on the deck. Fire pit, log burner, river views and countryside walks from the door.

Superhost
A comfortable seating area with white cushions is positioned on a deck overlooking the marina. Soft lighting gently illuminates the space, with a view of city lights and boats reflecting on the water, creating a serene evening atmosphere.
Boat in Ocean Village
4.88 out of 5 average rating, 120 reviews

Yacht "X" 44 foot modern yacht on 5* Ocean Village

A unique opportunity to stay onboard this newly renovated yacht moored on the beautiful Ocean Village Marina. Space for up to 5 guests to sleep (2 doubles and a single) Ideal for couples , families or small groups of friends to experience marina living. 2 en-suite bedrooms, living room, kitchenette, terrace, balcony and a spacious flybridge Bespoke packages available including afternoon teas, champagne reception, birthdays, spa access packages (walking distance) Please enquire for more details

Guest favourite
A modern open-plan living area features a gray sectional sofa adorned with patterned cushions. A wooden tray holds a bottle of wine on the sofa, while a textured area rug covers the floor. Wall shelves display framed photographs, and greenery adds a touch of nature.
Home in Woolston
4.94 out of 5 average rating, 250 reviews

2 bed House with Sea View and 2 parking spaces

Modern, open plan 2 bed house with garden, parking & great views from the Juliet balcony in the main bedroom. Perfect for people visiting Southampton and the Isle of Wight. Close to M27, bus & train stations. Ideal for local attractions such as Paulton's Park, Peppa Pig World, Portsmouth Historic Dockyard,The Mayflower Theatre, Gunwharf Quays & SeaCity Museum. Located right next to Weston shore & only 10 minutes to the city centre with plenty of bars and restaurants & West Quay Shopping Centre.

Top guest favourite
A private balcony features two sun loungers and a small coffee table, all positioned to take in vast sea views. A wooden railing complements the outdoor space, along with a shaded canopy overhead, creating a serene setting by the coast.
Treehouse in Ventnor
4.98 out of 5 average rating, 261 reviews

The Crow's Nest, Ventnor Beach (Hot Tub)

Looking for somewhere truly unique to stay? The Crow's Nest is the perfect beach hideaway. Think of it as your own luxury treehouse overlooking the sea, complete with a couples private hot tub. Winner of the 2019 & 22 Lux Travel Most Romantic Beachfront Accommodation. A cedar cabin nestled high into the cliffside overlooking Ventnor beach. It has bi-fold windows along two sides, opening up your room so it's just you, the sea and the horizon. The Crow's Nest is part of The Cabin, Ventnor Beach.

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, 451 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 cabin's exterior features natural wood paneling and large glass doors, inviting ample natural light. A wooden deck, adorned with a potted plant and equipped with a railing made of rope, provides an unobstructed view of the surrounding greenery.
Place to stay in Southbourne
4.99 out of 5 average rating, 137 reviews

The Little Gaff - One bedroom self contained cabin

The Little Gaff is a self contained cabin, located in an 'area of outstanding natural beauty' near the picturesque, harbour town of Emsworth. This beautiful harbourside village has many bars and restaurants and is surrounded by stunning countryside and wildlife. Little Gaff is situated in private grounds, on a secluded road, which provides secure accommodation and private parking. The cabin is raised up above road level, allowing spectacular, uninterrupted views across open marshes.

Top guest favourite
A corner seating area features a wooden table and two folding chairs, positioned near expansive windows that provide unobstructed views of the sea. Soft natural light floods the space, highlighting the light-colored wood paneling and enhancing the coastal ambiance.
Flat in Bracklesham Bay
4.94 out of 5 average rating, 180 reviews

Quirky & cool with amazing views to Isle of Wight

Quirky coastal property situated on the beach at Bracklesham Bay. This coastal inspired apartment is light and airy with dramatic sea views across to the Isle of Wight. Close to Chichester harbour and the South Downs and world renowned Goodwood, whether you’re a kite boarder or car enthusiast, this location has it all. Plenty of local restaurants and shops and with great fish and chips on your doorstep, you won’t have to venture far for that seaside experience.

Guest favourite
The motor yacht is docked at the marina, showcasing its sleek white exterior against a bright blue sky. A group of four people is situated on the bow, enjoying the sun and the scenic views of the surrounding cityscape.
Boat in Ocean Village
4.93 out of 5 average rating, 229 reviews

Superyacht on 5* Town Quay Marina, Southampton

A wonderful opportunity to stay onboard a beautiful spacious motor yacht moored on the prestigious Town Quay marina, Southampton. Ideal for couples, families or friends looking for an exciting or romantic getaway. Up to 6 guests. 3 bedrooms with 3 bathrooms. Bespoke packages also available including champagne reception, birthdays/decorations, secure cruise parking/transfers etc. Please enquire for details. Our base price is based upon 2 guests, extra guests are £25pp

Guest favourite
A charming garden stretches across the landscape, featuring lush greenery and a serene waterway. Two distinctive structures are visible: a traditional house and a converted mill, both surrounded by trees, creating a peaceful atmosphere by the River Meon.
Home in Exton
4.95 out of 5 average rating, 262 reviews

Romantic 17th Century Paper Mill on The Meon River

Enchanting converted 17th Century Paper Mill over the River Meon in Warnford, Hampshire. Quirky interior with original Japanese features. Trout anglers will have a ball. There are swans, herons, kingfishers and mallards and, if you're really lucky, you might see an otter. As you can see from the photo, the Mill is just by our cottage, but we're not always there so often you'd have the whole garden to yourself. My place is good for couples and solo adventurers.

Top guest favourite
The exterior of The New Dairy features a unique wooden structure with a sloped roof, surrounded by a gravel driveway. Large glass doors provide a view into the open-plan interior. Lush greenery borders the space, blending natural elements with the building's design.
Barn in Warsash
4.95 out of 5 average rating, 263 reviews

River Hamble Boutique Barn

Located 400m from the River Hamble in the small coastal village of Warsash in Hampshire. Perfect if you are studying at the Maritime College, are looking for a relaxing time near the water or as a base to explore further afield. The New Dairy has off road parking and easy access 24/7 Pubs, restaurants, takeaways and a Coop are within easy walking distance You will be welcomed with a complimentary basket that includes continental breakfast supplies.

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, 135 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.

Popular amenities for waterfront rentals in Winchester

Destinations to explore

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