Condo vacation rentals in Winchester

Find and book unique condos on Airbnb

Quick stats about condo rentals in Winchester

  • Total vacation rentals

    Explore 20 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at $100 per night before taxes and fees

  • Verified guest reviews

    Over 2,410 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Winchester vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winchester rentals

  • 4.9 Average rating

    Winchester stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated condo rentals in Winchester

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

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Top guest favorite
A light-filled living area features a comfortable gray sofa adorned with patterned cushions. A small, cozy armchair sits nearby, and a wooden coffee table is positioned in front. Natural light streams through the window, highlighting a light blue wall and decorative shelf.
Condo in Winchester
4.96 out of 5 average rating, 181 reviews

Spacious central 2 bedroom apartment+ free parking

A spacious family-friendly 2 double/twin bedroom first floor flat located in the lovely Hyde area of central Winchester. Provides easy access to the city centre with all that the city offers. Only 5 minutes stroll to the train station. This apartment is close to all the historical sites and wide variety of restaurants and cafes which you'll enjoy as well as the cathedral and its impressive grounds. Winchester Christmas market and the city's magical atmosphere should be on everybody's calendar.

Top guest favorite
Condo in Beggarwood
4.99 out of 5 average rating, 184 reviews

Basingstoke, Cosy 2-Bed Apt with private parking

This attractive 2-bedroom ground-floor home-from-home apartment has 2 parking spaces for your use lounge/dining room with comfortable sofa, armchair and table with chairs Fully equipped kitchen internal bathroom featuring a walk-in shower. Double room has, Double bed, and a single room with large 3ft single bed, Our apartment is smart enabled access from M3 Jct 7 and under 5 miles from Central Basingstoke nature parks within walking distance. Complementary beverages, Milk, biscuits, & snacks 👍

Superhost
A cozy living room is furnished with a spacious sectional sofa facing a wall-mounted TV. Large glass doors offer sweeping views of the sky and surrounding area. Green plants add a natural touch, while a sleek wood-burning stove creates a focal point in the inviting space.
Condo in Westbourne
4.85 out of 5 average rating, 194 reviews

The Beach Hytte - Stunning Sea View Penthouse

Enjoy your perfect getaway in this award winning 2 bed penthouse apartment with 180 degree sea views in the heart of the tranquil Alum Chine area of Bournemouth just a few minutes walk from the beach. The property boasts two dining areas, one of which sits on the large balcony with views across Bournemouth beach and a bespoke wood burning stove for the winter nights. The open plan kitchen leads onto a cozy living room where you can enjoy Sky Glass TV entertainment through super fast WiFi.

Superhost
Condo in Southampton
4.76 out of 5 average rating, 396 reviews

Central 2 Bed Apt in Sought After St. 4

This 2 bedroom apartment is beautifully decorated, and boasts charm and charisma from the grade 2 listed features of sash windows and a great view of Southamptons sought after Oxford Street which is filled with great bars and restaurants. Each bedroom has its own ensuite and there is free parking spot behind the gates within the private grounds. Your family will be close to everything when you stay at this centrally-located place. So conveniently situated to a varied array of amenities.

Top guest favorite
The exterior of the garden flat is showcased, featuring a sloped roof and large glass doors that open to a spacious terrace. A well-manicured lawn surrounds the building, and a dog relaxes peacefully in the grass. Lush greenery and garden beds enhance the inviting outdoor space.
Condo in Compton
5.0 out of 5 average rating, 139 reviews

Beautiful stylish Garden flat 8 mins to Winchester

Unique and stylish, this very comfortable and relaxing space offers the peacefulness of countryside whilst being a stones throw from the beautiful city of Winchester - a very short drive or a beautiful walk away. You get the best of both worlds with the city's pubs, restaurants, cafes and historic sights close at hand as well as river walks by the Itchen & beautiful countryside straight from your door. Excellent transport links to London, M3, Southampton Airport and the New Forest.

Guest favorite
The studio features an elegantly decorated sleeping area with a spacious bed adorned with a colorful bedding. Soft lighting highlights the intricate mirror and chandelier. A comfortable chair sits beside the bed, while large curtains frame the windows, adding to the cozy ambiance.
Condo in Winchester
4.91 out of 5 average rating, 216 reviews

Bright Bijou Studio in Central Winchester

A beautiful bright cosy studio apartment on one of the quietest streets in the centre of historic Winchester❤️. The breathtaking cathedral and other must-see sights are all within a flat 10 minute walk. Ideal for short stays or a weekend get-away. Just five minutes walk from train station/city centre, and 10 mins walk from the bus station. * Super-comfy double bed ✅ * Fast WiFi ✅ * Comfortable big chair and table for laptop working ✅ * Wide range of caf/decaf teas and coffees ✅

Guest favorite
The living room features a light and airy design, showcasing a two-seater sofa and a separate sofa bed. A dining table for four is centered in the space, complemented by a fireplace and a wall-mounted TV. Decorative plants enhance the welcoming atmosphere.
Condo in Winchester
4.92 out of 5 average rating, 248 reviews

Stylish Apartment • Central Winchester

Situated in the heart of Winchester, this newly refurbished two-bedroom apartment with its own private entrance offers a stylish and comfortable stay for couples, friends and families. Modern décor and thoughtful design create a cosy space to relax after exploring the city’s historic streets, shops and cathedral. You’re just steps from the popular St James Tavern, a welcoming traditional pub serving excellent locally sourced food.

Guest favorite
Condo in Southampton
4.83 out of 5 average rating, 356 reviews

Entire Studio Apartment • Private Entrance •

This is a very bright and stylish apartment. Good size living area, with modern furniture and a relaxing, comfortable feel. Stylish kitchen and bath room, dining table and seating. Perfect for city visits, either business or pleasure. Walking distance to all city attractions. Great for shopping, entertainment, theatres, all within a 10 minute walk away, and cruise base. 🛳 Cruise parking available (message us for details).

Guest favorite
A living area is depicted with a comfortable sofa, a coffee table, and a television displaying a streaming service. Natural light floods in through multiple glass doors leading to a balcony. A desk is positioned nearby, accompanied by a chair and plants adding to the ambiance.
Condo in Southampton
4.9 out of 5 average rating, 115 reviews

Top-floor retreat with views & free parking

Step into a stylish top-floor flat with stunning skyline views, private balcony and secure parking. Just 10–15 mins to the city centre, 15–20 mins to the cruise terminal and 1.6 miles from Southampton airport with fast M27/M3 access. Nearby buses and e-bikes make exploring easy. Bright, modern and peaceful, it’s the perfect base - whether you’re here for Southampton, a cruise, or adventures across Hampshire.

Guest favorite
The exterior of Little Bunty Lodge is presented, showcasing a charming single-story structure partially draped in greenery. A pebbled driveway leads to the entrance, framed by well-maintained hedges. The building's rustic roof and windows accent its inviting character amidst a serene natural setting.
Condo in New Milton
4.89 out of 5 average rating, 254 reviews

Luxurious Apartment in New Forest National Park

Little Bunty Lodge is ideal for a romantic getaway or a peaceful solo retreat, this luxurious studio offers comfort and style. A great base to explore the beautiful New Forest, with ponies and deer roaming free, as well as the stunning local beaches. Barton beach 3 miles Avon beach 6.5 miles Lymington 7.5 miles Christchurch 7 miles Bournemouth 14 miles Southampton with West Quay shopping complex 18.5 miles

Top guest favorite
Condo in Winchester
4.92 out of 5 average rating, 286 reviews

Stable Apartment with Hot Tub near Winchester

Newly renovated apartment with copper bath and hot tub in a converted stable 3 miles from Winchester. The well-equipped kitchen has a table seating six, alongside a boot room/utility, and sitting room with flame effect fire. Guests have access to the owner’s pool (May to September) and tennis court. Private hot tub and fenced garden with outdoor furniture.

Top guest favorite
A modern living area features a sleek gray sofa adorned with a light throw blanket. A glass coffee table sits in front, accompanied by a small dining table with two chairs. Colorful wall art enhances the space, while large windows offer views of the surrounding area.
Condo in Gunwharf Quays
4.86 out of 5 average rating, 407 reviews

FAR REACHING HARBOUR VIEWS

Newly renovated One bedroom apartment that is part of Portsmouth Iconic "The Hard". Well proportioned double bedrooms both with built in wardrobes. Views over Portsmouth historic dockyard and as far reaching as the Solent and Isle of White. Located with in 2 minutes walk of Gunwharf Quays and The Hard train and Portsmouth's Historic Dockyard.

Popular amenities for Winchester condo rentals

When is the best time to visit Winchester?

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