
Apartment holiday rentals in Winchester
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Top-rated apartment rentals in Winchester
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Little Trout, Nether Wallop: an oasis of calm
Little Trout is the annex to a 17th century thatched cottage. A one-bedroom flat with fully equipped kitchen, large shower and comfortable sitting room, it is perfect for a trip to West Hampshire and the Test Valley. You will find an oasis of calm in a busy world where you can relax in comfort after an active day visiting the many sites of historic interest or admiring our beautiful local scenery. Almost all our guests have told us that the bed is the most comfortable they have ever slept in!

Copper Beech, a secluded two bed apartment
Copper Beech is spacious & modern apartment in a semi-rural location close to Winchester. This apartment has two large king size bedrooms; both with ensuite bathrooms, large lounge/dining area and a well equipped kitchen. One of the bedrooms can sleep up to 4 guests with a daybed (with two full single size beds) plus kingsize bed. Parking is available for two standard-sized vehicles - one blocking in the other. There is a trampoline in a large shared garden for children to play on.

Exceptional room and study area.
This is the majority of a furnished annexe (no kitchen) located in Burridge , which is half-way between Portsmouth and Southampton. About a mile away from both Swanwick Marina and Park Gate village, Swanwick train station is 15 minute walk. With it's own entrance comprising of main bedroom/sitting area, separate study area and separate shower room. There is space to park a car off the road. A convenient base to visit Winchester, Portsmouth, Southampton and The New Forest. Self check in.

The Ocean Suite, Ventnor Beach (with Sauna)
The ultimate in beachfront living, a perfect romantic escape and popular with many repeat guests. A cedar cabin with panoramic sea views over Ventnor beach, winner of 2025 LUXLife Magazine Awards, Best Coastal Retreat, South England. 52 sq metres and open plan, with bi-fold windows/doors creating a beautiful space of just you and the ocean. With 2 private balconies, 1 south facing for sunbathing, the other perfect for an alfresco breakfast in the morning sun. No pets but baby welcome!

The Annexe at Longacre, near Winchester
The Annexe is a bright and airy self contained house separate from our home. The accomodation is over two floors with wonderful views out to the Hampshire countryside. We are on a quiet private country road 2 miles from the vibrant city of Winchester, 6 miles from Southampton Airport and 3 miles from IBM Hursley. Excellent transport links to London (1 hour from Shawford Station) and to Southampton. We live in the main house. Follow us on Instagram @longacreannexe

Central Winchester garden flat, permit parking
Winchester City Centre- Bijou, charming, characterful, homely, warm and cosy self contained one bedroom flat with free permit parking and luxuriously large bath tub with shower, private garden with patio for alfresco dining. Fully equipped galley kitchen for self - catering. Only a five minute level walk to the central High Street and Cathedral, with the world famous Christmas Market through November and December. Less than ten minutes walk from the Railway Station.

A Discreet Hampshire Downs Retreat for Quiet Stays
Set within the rolling Hampshire Downs, this thoughtfully designed annexe offers rare privacy, calm and refined simplicity. Evenings invite slow living beside your wood burner, while mornings begin beneath the luxury outdoor hot-water shower, immersed in countryside stillness. Designed as I like to travel myself, every detail is intentional, understated and quietly indulgent — a discreet retreat for guests who value space, quality and uninterrupted rest.

The Studio @ Black Barn, Nr Petersfield.
Newly refurbished, ‘The Studio at Black Barn’ is an open plan self-contained private annexe with own parking right outside its own private entrance and garden. Your accommodation is on the ground floor of a family home, surrounded by countryside near Petersfield. Perfect for 1 or 2 adults to indulge in a relaxing mini break; also ideal for a fleeting overnight work visit and take advantage of the superfast broadband to work from Black Barn.

Modern Apartment Central Winchester
Situated in the heart of Winchester, this newly refurbished 2-bedroom apartment with its own private entrance and modern décor provides a well thought out space for friends, couples & families. This cosy home provides an excellent upmarket base to explore Winchester. A stone’s throw to the city’s favourite pub, St James Tavern, a warm welcoming traditional pub which serves excellent locally sourced home cooked food.

** Stylish, clean and modern apartment **
Clean, wonderfully modern and ideally located en-suite maisonette within close proximity to the following: * Peppa Pig World / Paultons Park (15 minute drive) * Marwell Zoo (20 mins) * Southampton Airport (5 mins) * Winchester (15 mins) * Southampton Cruise Terminal (20 mins) * The New Forest (20 mins) A great and comfortable apartment with all you need for a relaxing stay.

Riverside Retreat - Free Parking
Take it easy at this unique and tranquil getaway overlooking the river. Being a stone throw from Southampton central, it’s close enough to be in town within a 5-10 minute car journey but far enough away to slow down. The property offers a large wraparound balcony from master bedroom to lounge diner. Making it a wonderful spot for indoor outdoor living.

*Stunning River Views*, modern in great location
New, modern and bright apartment next to the River Itchen with awesome river views from balcony in an excellent location! Close to Ocean Village with high end furnishings and close to popular amenities, and a short walk to the city centre, and short transfers to cruise terminals.
Popular amenities for Winchester apartment rentals
Weekly apartment rentals

Self Contained Annex

Stylish2Bed-OASIS in heart of village-ParkingSpace

Roomy self-contained annex near Highclere Castle

The Sky Penthouse, City Centre Luxury

Comfortable Central Winchester Garden Apartment

Self Catering Ground Floor Flat

No 2 The Old School House, Winchester with parking

Luxury 2BR apartment + parking central Winchester
Private apartment rentals

A new detached Studio Annexe

Historic Winchester Apartment

Lymington Apartment with parking

Self Contained Annexe Hampshire

The best views in Southsea

Cosy Flat | Near City Center, Hosp. & Uni

1 Bed Apartment - Sea view

A gorgeous spacious 2 bedroom apartment in centre
Apartment rentals with a hot tub

Monopoly Suite - Jacuzzi Bath

Seaside Escape-Garden, Hot Tub, Sleeps 8 in Style

New Forest Hideaway

Little Gem in Old Village - Up to 25% off ferry!

Luxury Apartment Near Beach & Trendy Restaurants

Bright 2-Bed Getaway | Hot Tub • Swimming Pool

Bright2BRApt | QuickGetaway | Sun Terrace| Hot Tub

Chic Coastal Apartment | Central Location
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $133 SGD | $135 SGD | $145 SGD | $161 SGD | $174 SGD | $188 SGD | $191 SGD | $189 SGD | $175 SGD | $173 SGD | $173 SGD | $170 SGD |
| 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 |
Quick stats about flat rentals in Winchester

Total holiday rentals
Explore 70 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 5,130 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
70 of Winchester holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winchester rentals

4.6 Average rating
Winchester stays receive an average rating of 4.6 out of 5 from guests
Destinations to explore
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- New Forest National Park
- Paultons Park Home of Peppa Pig World
- University of Oxford
- Goodwood Motor Circuit
- Bracklesham Bay
- Stonehenge
- Windsor Castle
- Hampton Court Palace
- Lower Mill Estate
- Highclere Castle
- Boscombe Beach
- Winchester Cathedral
- Chessington World of Adventures Resort
- Thorpe Park Resort
- Bournemouth Beach
- Kimmeridge Bay
- Goodwood Racecourse
- Highcliffe Beach
- The Tank Museum
- Worthing Pier
- West Wittering Beach
- Southbourne Beach
- Wentworth Golf Club
- RHS Garden Wisley




