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
Individually-styled studio room with double bed
Sleeps 2
1 Bedroom
1 Bathroom
Wifi/Internet
Parking
Garden
Apartment
in Southampton, The New Forest
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
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
New Forest Cottages with fishing on the doorstep - April 2026 Offer. Dogs go FREE 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
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
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
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
The Coach House
Sleeps 6
3 Bedrooms
2 Bathrooms
Child Friendly
Wifi/Internet
Parking
Garden
EV Charger
House
in Hambledon, waterlooville, Hampshire
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
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
Little Hayes
Sleeps 14
7 Bedrooms
7 Bathrooms
Child Friendly
Wifi/Internet
Parking
Garden
House
in Lyndhurst, Hampshire
Quay Corner is a Coastal Town House in the heart of Christchurch, Dorset with hot tub woodburner - *April 2026 Offer. Dogs go FREE when you book a break for 2026!*
Sleeps 10
5 Bedrooms
3 Bathrooms
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Hot Tub
Garden
EV Charger
House
in Christchurch, Dorset
Charming New Forest barn with log burner, private garden, and spiral staircase. Ideal for couples and dog lovers seeking a peaceful rural retreat in the heart of the new forest. private patio garden with BBQ,
Sleeps 2
1 Bedroom
1 Bathroom
Pet Friendly
Wifi/Internet
Parking
Garden
Holiday Cottage
in Redlynch, salisbury, The New Forest
1 Car Ferry Included* This delightful cottage is situated a short stroll from the centre of the historic and picturesque harbour town of Yarmouth. The cottage provides accommodation for couples and small families alike.
Sleeps 2
2 Bedrooms
2 Bathrooms
Child Friendly
Wifi/Internet
Holiday Cottage
in Yarmouth, Isle Of Wight
1 Car Ferry Included* Property sleeping 6 with a king, double, and bunk bedroom. Features include a newly refurbished bathroom, free Wi-Fi, Smart TV, fully equipped kitchen, and close to waterfront and pubs
Sleeps 6
3 Bedrooms
1 Bathroom
Child Friendly
Wifi/Internet
Parking
Garden
Holiday Cottage
in East cowes, Isle Of Wight
Barbury Cottage is an 18th century quirky little cottage in the Southdowns National Park
Sleeps 4
2 Bedrooms
1 Bathroom
Pet Friendly
Wifi/Internet
Garden
Holiday Cottage
in Sheet, Petersfield, Hampshire
1 Car ferry included Cape 8 cosy retreat near local amenities and close to the pretty town of Yarmouth and it's harbour.
Sleeps 4
2 Bedrooms
1 Bathroom
Child Friendly
Wifi/Internet
Parking
Bungalow
in Yarmouth, Isle Of Wight
1 Car Ferry Included* Beachside in Bembridge is situated just yards from the beach this stunning ‘New England’ style house enjoys fabulous sea views and gardens leading onto the beach.
Sleeps 6
4 Bedrooms
3 Bathrooms
Child Friendly
House
in Newport, Isle Of Wight
Lubbers: Wellies & Windbreaks Holiday Rental
Sleeps 10
5 Bedrooms
4 Bathrooms
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Garden
House
in West wittering, West Sussex
Marigold Cottage: Wellies & Windbreaks Holiday Rental
Sleeps 4
2 Bedrooms
1 Bathroom
Child Friendly
Pet Friendly
Wifi/Internet
Garden
Holiday Cottage
in East wittering, West Sussex
Dots: Wellies & Windbreaks Holiday Rental
Sleeps 11
6 Bedrooms
3 Bathrooms
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Garden
House
in East wittering, West Sussex
A bright and comfortable four-bedroom coastal home tucked just off St Helens Green, perfectly placed for walks to the Duver and the beach. Off street parking, fully enclosed private garden DISCOUNTED FERRY TICKETS
Sleeps 8
4 Bedrooms
3 Bathrooms
Child Friendly
Pet Friendly
Wifi/Internet
Parking
House
in Isle Of Wight, England
1 Car Ferry Included* Property in Wootton Creek. Has its own decking with furniture, and shared gardens go down to the creek edge.
Sleeps 4
2 Bedrooms
2 Bathrooms
Pet Friendly
Parking
Garden
Villa Rental
in Wootton bridge, Isle Of Wight
A charming, family-friendly cottage
Sleeps 6
3 Bedrooms
3 Bathrooms
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Garden
Holiday Cottage
in Milford on sea, Hampshire
Rox: Wellies & Windbreaks Holiday Rental
Sleeps 12
5 Bedrooms
4 Bathrooms
Child Friendly
Wifi/Internet
Parking
Garden
House
in West wittering, West Sussex
'Cliffway' a real gem, peaceful 2 bed cottage with own sunny gdn, sea-view, few mins walk to beach, coastal path & sea-front restaurants. A lovely place to relax/let cooling air flow through the hse. Wightlink discounts.
Sleeps 5
2 Bedrooms
1 Bathroom
Child Friendly
Wifi/Internet
Parking
Garden
Holiday Cottage
in Totland Bay, Isle Of Wight
Spacious 4 bed house, short walk to Yaverland beach
Sleeps 8
4 Bedrooms
3 Bathrooms
Child Friendly
Wifi/Internet
Parking
Garden
House
in Yaverland, Isle Of Wight
1 Car Ferry Included* 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
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
1 Car ferry included* The village is located amidst beautiful countryside, some of which bears Area of Outstanding Natural Beauty or Site of Special Scientific Interest designations.
Sleeps 4
2 Bedrooms
1 Bathroom
Child Friendly
Wifi/Internet
House
in Wootton bridge, Isle Of Wight
Renovated Art Deco Beachside Home in East Wittering with Modern Interiors, Garden, Balcony & Flexible Sleeping Layout
Sleeps 10
5 Bedrooms
3 Bathrooms
House
in East wittering, West Sussex
1 Car Ferry Included* Downedge is approached via its own private driveway to a large turning circle with plenty of space for cars to park.
Sleeps 13
6 Bedrooms
4 Bathrooms
Child Friendly
Pet Friendly
Parking
Garden
House
in Brading, Isle Of Wight
1 Car Ferry Included* Harbour Walk is in a quiet, tucked away close, a short walk from Bembridge harbour and beaches
Sleeps 6
3 Bedrooms
2 Bathrooms
Child Friendly
Pet Friendly
Wifi/Internet
Parking
House
in Bembridge, Isle Of Wight
Looking for a peaceful retreat that offers both comfort and style? Number One Bembridge House is your perfect sanctuary, just a stone's throw away from the picturesque harbour and beach DISCOUNTED FERRY TICKETS
Sleeps 7
3 Bedrooms
2 Bathrooms
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Garden
House
in Bembridge, Isle Of Wight
Number Twenty Four Wellies & Windbreaks Holiday Rental
Sleeps 10
4 Bedrooms
3 Bathrooms
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Hot Tub
Garden
House
in West wittering
Little Orchard: Wellies & Windbreaks Holiday Rental
Sleeps 5
5 Bedrooms
4 Bathrooms
Child Friendly
Wifi/Internet
Parking
Hot Tub
Garden
EV Charger
House
in West wittering, West Sussex
1 Car ferry included* Detached lodge located on a peaceful country park
Sleeps 6
3 Bedrooms
2 Bathrooms
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Hot Tub
Lodge
in Ryde, Isle Of Wight
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
Comfortable period house overlooking St Helen's village green, Isle of Wight
Sleeps 9
4 Bedrooms
3 Bathrooms
Child Friendly
Wifi/Internet
Garden
House
in Isle Of Wight, England
Serene Roman Landing Home Near West Wittering Beach with Garden Views, Flexible Living Spaces & Outdoor Dining
Sleeps 8
2 Bedrooms
2 Bathrooms
House
in West wittering, West Sussex
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
1 Car Ferry Included* This charming semi-detached cottage in Yarmouth is just 0.5 miles from the beach and within walking distance of the promenade, pier, and local amenities. Perfect for exploring the island’s beauty.
Sleeps 4
2 Bedrooms
1 Bathroom
Child Friendly
Pet Friendly
Parking
Garden
Holiday Cottage
in Yarmouth, Isle Of Wight
1 Car Ferry Included* Coastal Cottage is the ideal family getaway, Whether you’re seeking relaxation or adventure, this home provides the perfect escape.
Sleeps 6
3 Bedrooms
1 Bathroom
Child Friendly
Pet Friendly
Wifi/Internet
Parking
Garden
Bungalow
in Bembridge, Isle Of Wight
1 Car ferry included* Welcome to this immaculate bungalow located in the beautiful West Wight area.
Sleeps 6
3 Bedrooms
2 Bathrooms
Child Friendly
Wifi/Internet
Parking
Bungalow
in Yarmouth, Isle Of Wight
1 Car Ferry Included* A Stylish Three-Storey Riverside Retreat at Island Harbour Marina with Panoramic River Views, Spacious Balconies, Flexible Bedrooms & Private Berth, Perfect Base to Explore the Isle of Wight
Sleeps 6
3 Bedrooms
2 Bathrooms
House
in Newport, Isle Of Wight
- Holiday Cottages UK
- England
- Hampshire
- Winchester
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