
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.

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.

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 👍

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.

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.

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.

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 ✅

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.

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).

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.

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

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.

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
Weekly condo rentals

Luxury 2 Bed Apartment | River Views | Parking

Pier View Retreat - Sea Views - With Parking

The Perch, stay in the heart of the New Forest

Contemporary Penthouse Apartment Southampton City

The Suite, Chichester, England,

Welcoming apartment in the heart of the New Forest

Modern Beach Side apartment with easy access.

Elegant home, minutes from beach, free parking!
Pet-friendly condo rentals

Self-contained 2 king bed Flat 11 acres woodland

Coach House Flat in South Downs National Park.

The Old Dairy at Heads Hill Farm

Self-contained flat, a 4 minute walk from the sea

Cozy Midhurst Apartment: Walk to Town Centre

Studio Flat on New Forest National Park border

Luxury flat on Sandbanks beach with panorama view

Modern town apartment 2 mins from water.
Condo rentals with a pool

'The Nest' near Arundel

Myrtle Retreat

Luxury Penthouse: Spacious & Stylish

2-BR Penthouse Apt. close to Beach with Pool*.

Beach Lookout - FREE Car Ferry 3+ nights

The Palms, Apartment 20

Flat 10 Pelican House

Guest house in Pewsey Vale with pool
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $135 | $136 | $138 | $135 | $154 | $151 | $129 | $137 | $139 | $167 | $134 | $178 |
| Avg. temp | 41°F | 41°F | 45°F | 49°F | 54°F | 59°F | 63°F | 63°F | 58°F | 52°F | 46°F | 41°F |
Destinations to explore
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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
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