Winchester Holiday Cottages
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- Holiday Cottages UK
- England
- Hampshire
- Winchester
Holiday Cottages in Winchester
Find your perfect self-catering holiday cottage in and around Winchester. Book direct with owners and pay no booking fees. Book with confidence. All our holiday rentals are verified and backed by our payment protection.
Holiday Cottages in Winchester, Hampshire
Modern family flat in central Brockenhurst with parking, Smart TV, and games — perfect for exploring the New Forest and enjoying village life.
Sleeps 4
2 Bedrooms
1 Bathroom
Child Friendly
Wifi/Internet
Parking
Apartment
in Hampshire, England
Forest Gate Lodge Annex is a beautiful place for that relaxing break.
Sleeps 2
1 Bedroom
1 Bathroom
Pet Friendly
Wifi/Internet
Parking
Garden
Bungalow
in Wickham, Hampshire
Little Hayes
Sleeps 14
7 Bedrooms
7 Bathrooms
Child Friendly
Wifi/Internet
Parking
Garden
House
in Lyndhurst, Hampshire
Stylish modern apartment. Private off-street parking for exclusive use of guests
Sleeps 4
2 Bedrooms
1 Bathroom
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Garden
Apartment
in Southampton, The New Forest
Beautiful forest-view cottage with large garden, BBQ, and direct New Forest access. Perfect for families, nature lovers, and peaceful countryside getaways.
Sleeps 8
4 Bedrooms
3 Bathrooms
Child Friendly
Wifi/Internet
Parking
Garden
Holiday Cottage
in Brockenhurst, The New Forest
Stylish modern 1-bedroom apartment. Private off-street parking
Sleeps 2
1 Bedroom
1 Bathroom
Wifi/Internet
Parking
Garden
Apartment
in Southampton, The New Forest
The Coach House
Sleeps 6
3 Bedrooms
2 Bathrooms
Child Friendly
Wifi/Internet
Parking
Garden
EV Charger
House
in Hambledon, waterlooville, Hampshire
Stable Cottage. Quiet, accessable cottage set in the Meon Valley. Pet Friendly, fully enclosed private garden. wheelchair accessible
Sleeps 2
1 Bedroom
1 Bathroom
Pet Friendly
Wifi/Internet
Parking
Garden
Holiday Cottage
in Southampton, England
Individually-styled studio room with double bed
Sleeps 2
1 Bedroom
1 Bathroom
Wifi/Internet
Parking
Garden
Apartment
in Southampton, The New Forest
Spacious coastal cottage with hot tub, garden and two lounges near beach – ideal for families and groups seeking comfort and calm.
Sleeps 10
3 Bedrooms
4 Bathrooms
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Hot Tub
Garden
Holiday Cottage
in Calshot, The New Forest
New Forest Cottages with fishing on the doorstep - March 2026 Offer. Half price hot tub when you book a break for 2026!*
Sleeps 23
10 Bedrooms
8 Bathrooms
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Hot Tub
Garden
EV Charger
Holiday Cottage
in The New Forest, England
Island Escape 2 Bed Fully Equipped Coastal Themed Dog Friendly Holiday Home In Excellent Location In Sandown Isle Of Wight
Sleeps 5
2 Bedrooms
1 Bathroom
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Pool
Caravan
in United Kingdom
Offering a comfortable, family-friendly home with 3 bedrooms, 2 en-suites, a family shower room, and an enclosed garden. Close to Forelands Beach, local eateries, and fishing trips.
Sleeps 6
3 Bedrooms
3 Bathrooms
Child Friendly
Wifi/Internet
Parking
Garden
Lodge
in Bembridge, Isle Of Wight
20% Discount for summer 2025 A stylish and spacious three-bedroom detached house, just a couple of minutes' walk from the beach
Sleeps 5
3 Bedrooms
1 Bathroom
Child Friendly
Wifi/Internet
Parking
Garden
House
in Bembridge, Isle Of Wight
Semi-detached coastal retreat in Bembridge with beach access, sunroom, and scenic harbour and countryside views.
Sleeps 4
2 Bedrooms
2 Bathrooms
Pet Friendly
Wifi/Internet
Parking
Garden
Holiday Cottage
in Bembridge, Isle Of Wight
Seamark: Wellies & Windbreaks Holiday Rental
Sleeps 10
4 Bedrooms
4 Bathrooms
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Garden
EV Charger
House
in East wittering, West Sussex
Spacious first-floor cottage with stunning lake views, large private garden, open-plan living, and access to farm animals, fishing lakes, and outdoor play areas.
Sleeps 8
3 Bedrooms
1 Bathroom
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Garden
EV Charger
Holiday Cottage
in Isle Of Wight, England
Stylish seaside apartment with sea views, contemporary kitchen, and a private balcony. Perfectly located on the beach-front in East Wittering, with shops and restaurants nearby.
Sleeps 4
2 Bedrooms
1 Bathroom
Child Friendly
Wifi/Internet
Parking
EV Charger
Apartment
in East wittering, England
Forest Drove in the New Forest is a quintessential thatched cottage filled with charm, large dining room in bright extension and games room - March 2026 Offer. Half price hot tub when you book a break for 2026!*
Sleeps 12
6 Bedrooms
3 Bathrooms
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Hot Tub
Garden
EV Charger
Holiday Cottage
in The New Forest, England
Stunning property in Bembridge with Heated Swimming Pool, Tennis Court, 5 Bedrooms all with ensuite bathrooms
Sleeps 10
5 Bedrooms
4 Bathrooms
Child Friendly
Wifi/Internet
Parking
Garden
Pool
House
in Isle Of Wight, England
Beachwood: Wellies & Windbreaks Holiday Rental
Sleeps 10
5 Bedrooms
4 Bathrooms
Child Friendly
Wifi/Internet
Parking
Garden
House
in West wittering, West Sussex
Creek, Kipper Cottage provides comfortable and very well presented accommodation for 4 people
Sleeps 4
2 Bedrooms
2 Bathrooms
Child Friendly
Pet Friendly
Wifi/Internet
Garden
Holiday Cottage
in Wootton bridge, Isle Of Wight
Sandcove is one of Bembridge’s most sought-after holiday homes — a spacious coastal retreat sleeping 8/10 guests with uninterrupted views across the Solent. Garden room with Sauna & Views DISCOUNTED FERRY TICKETS
Sleeps 10
4 Bedrooms
3 Bathrooms
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Garden
EV Charger
House
in Bembridge, Isle Of Wight
Spacious & light, comfortably furnished, newly decorated throughout. You walk in the door & feel like you are on holiday, seconds from the beach & amenities of Seaview. Dogs & children welcome. DISCOUNTED FERRY TICKETS
Sleeps 6
3 Bedrooms
2 Bathrooms
Child Friendly
Pet Friendly
Wifi/Internet
Holiday Cottage
in Isle Of Wight, England
Beachside East Wittering Townhouse with Modern Open-Plan Living, Garden, BBQ, Parking & Pet-Friendly Features
Sleeps 7
4 Bedrooms
2 Bathrooms
House
in East wittering, West Sussex
Detached, 4 Star cottage. Two bedrooms each en-suite. Sleeps 4. Open plan living. Garden, Games Room. Walking/Cycling, Moors Valley activities. New Forest/Dorset border, choice of beaches. No fees. Best Price Guaranteed.
Sleeps 4
2 Bedrooms
2 Bathrooms
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Garden
EV Charger
Holiday Cottage
in Verwood, Dorset
Peaceful clifftop chalet with private terrace, sea views and easy access to beach walks. Light, comfortable interiors, a quiet setting and everything you need for a relaxed Isle of Wight break. GENEROUS FERRY DISCOUNT.
Sleeps 6
2 Bedrooms
1 Bathroom
Child Friendly
Wifi/Internet
Parking
Chalet
in Yaverland, Isle Of Wight
Dairy Cottage - delightful superb accommodation in rural setting in ideal location. Easy access to the New Forest, south coast beaches and medieval Salisbury.
Sleeps 2
1 Bedroom
1 Bathroom
Pet Friendly
Wifi/Internet
Parking
Garden
Holiday Cottage
in Fordingbridge, Dorset
Cornwall Cottage is a stunning family home located in the village of Seaview, just a short walk from local shops and the beautiful beaches. Offering relaxed and flexible accommodation for 10. DISCOUNTED FERRY TICKETS
Sleeps 10
5 Bedrooms
3 Bathrooms
Child Friendly
Wifi/Internet
Parking
Garden
Holiday Cottage
in Isle Of Wight, England
This stunning family friendly historic cottage is steps away from the shoreline of Bosham, has private garden with furniture, breath-taking views, a boathouse, close to the local amenities, WIFI. Parking.
Sleeps 6
3 Bedrooms
3 Bathrooms
Child Friendly
Wifi/Internet
Parking
Garden
Holiday Cottage
in Bosham, West Sussex
Woodlands : Perfect for birthday weekends, get togethers and getaways, separate dining room, elegant and comfortable DISCOUNTED FERRY TICKETS
Sleeps 10
5 Bedrooms
3 Bathrooms
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Garden
House
in Bembridge, Isle Of Wight
Charming 2 / 3-Bedroom Cottage with Garden, Conservatory & Castle Views – Near Newport
Sleeps 6
2 Bedrooms
1 Bathroom
Child Friendly
Wifi/Internet
Parking
Garden
Holiday Cottage
in Newport, Isle Of Wight
Discover this charming 2-bedroom house located in Bembridge, Isle of Wight. Perfectly combining modern style with period character, this beautifully restored seaside home. DISCCOUNTED FERRY TICKETS
Sleeps 4
2 Bedrooms
1 Bathroom
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Garden
EV Charger
House
in Bembridge, Isle Of Wight
Beautiful holiday chalet in the New Forest with fishing on the doorstep - 5 star Guests say the best location. Secure
Sleeps 11
5 Bedrooms
4 Bathrooms
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Hot Tub
Garden
EV Charger
Bungalow
in Fordingbridge, Dorset
Beautiful, dog friendly barn, set on a rural working farm on the edge of the stunning New Forest National Park.
Sleeps 4
2 Bedrooms
2 Bathrooms
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Barn
in The New Forest, Ringwood
*Celebration house, walking distance of pub & sea*
Sleeps 15
6 Bedrooms
4 Bathrooms
Child Friendly
Wifi/Internet
Parking
Garden
EV Charger
House
in Chichester, West Sussex
Grade II listed Thatched Cottage In The Village of Carisbrooke. Superbly quite position and 10 mins into Newport. Views up to Carisbrooke Castle. Good walking area.
Sleeps 8
4 Bedrooms
3 Bathrooms
Child Friendly
Wifi/Internet
Parking
Garden
Holiday Cottage
in Isle Of Wight, England
The Quays in Christchurch Dorset a lovely house the sleeps 25 for large groups - *March 2026 Offer. Half price hot tub when you book a break for 2026!*
Sleeps 25
11 Bedrooms
7 Bathrooms
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Hot Tub
Garden
EV Charger
House
in Christchurch, Dorset
Escape to this charming thatched cottage—a picture-perfect retreat nestled among green spaces and historic landmarks. This beautifully furnished holiday home blends rustic elegance with modern comfort
Sleeps 4
2 Bedrooms
2 Bathrooms
Child Friendly
Wifi/Internet
Parking
Garden
Holiday Cottage
in Wellow, yarmouth, Isle Of Wight
New Forest Thatched Cottage with hot tub and games room -March 2026 Offer. Half price hot tub when you book a break for 2026!*
Sleeps 14
7 Bedrooms
5 Bathrooms
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Hot Tub
Garden
EV Charger
Holiday Cottage
in The New Forest, England
Samphire: Wellies & Windbreaks Holiday Rental
Sleeps 6
3 Bedrooms
4 Bathrooms
Child Friendly
Wifi/Internet
Parking
Garden
House
in West wittering, West Sussex
28 Anchorage Way has views across the River Medina to East Cowes Marina.
Sleeps 4
2 Bedrooms
1 Bathroom
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Garden
House
in East cowes, Isle Of Wight
- Holiday Cottages UK
- England
- Hampshire
- Winchester
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Properties marked with a rainbow have discounts for NHS & social care workers.See individual properties for details.
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