Skip to main content

Self-Catering Cottages in Winchelsea

30 holiday cottages to rent

Cottage
Eagles Nest at Greyfriars from £1,788

Rother · 0.1 miles away

Eagles Nest at Greyfriars

Grade II listed wing in Winchelsea with hot tub, two miles from Rye and near Camber Sands.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
Heron’s Wood at Greyfriars from £1,788

Rother · 0.1 miles away

Heron’s Wood at Greyfriars

Grade II listed ground-floor wing near Winchelsea village, two miles from Rye, with hot tub and direct beach access.

🛏️ 2 beds 👥 Sleeps 5 🐾 Pets welcome
Cottage
Winchelsea Cottage from £433

Rother · 0.1 miles away

Winchelsea Cottage

Three-bedroom cottage in Winchelsea village, five minutes from the beach and walking routes through the Sussex countryside.

🛏️ 3 beds 👥 Sleeps 5
Cottage
Henry Oscar House from £1,622

Rother · 0.3 miles away

Henry Oscar House

Four-bedroom house in Rother with hot tub, fully equipped kitchen and all essentials included.

🛏️ 4 beds 👥 Sleeps 8 🐾 Pets welcome
Bluebell Haven from £668

Rother · 0.8 miles away

Bluebell Haven

Bluebell Haven, Battle: a campground with en-suite pitches, on-site food, and woodland setting near Crowhurst.

👥 Sleeps 4
Cottage
Newhope from £403

Rother · 0.9 miles away

Newhope

One-bedroom cottage on the East Sussex coast, a short walk from Camber Sands beach and Rye Harbour Nature Reserve.

🛏️ 1 bed 👥 Sleeps 2 🐾 Pets welcome
The Lodge at Winchelsea from £931

Rother · 1.1 miles away

The Lodge at Winchelsea

Two-bedroom holiday home in Winchelsea, a historic Cinque Port town near the Sussex coast, with parking and modern facilities.

🛏️ 2 beds 👥 Sleeps 4
Cottage
Kiln Cottage

Rother · 1.9 miles away

Kiln Cottage

One-bedroom cottage in Rother, fully equipped with heating, cooker and washing machine, one dog welcome.

🛏️ 1 bed 👥 Sleeps 2 🐾 Pets welcome
Cottage
Harbour Retreat

Rother · 2 miles away

Harbour Retreat

Six-bedroom luxury house in Rye sleeping 12, with two living rooms and a private garden; one dog welcome.

🛏️ 6 beds 👥 Sleeps 12 🐾 Pets welcome
Cottage
The Quarter House from £347

Rother · 2 miles away

The Quarter House

Two-bedroom apartment in Rye with exposed beams and open fire, within walking distance of beaches and the Sussex coast.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
Cottage
66 Fish from £463

Rother · 2.2 miles away

66 Fish

66 Fish, Rother: two-bedroom coastal house with off-street parking and enclosed garden, one dog welcome.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
Cottage
Garden Cottage from £467

Rother · 2.6 miles away

Garden Cottage

One-bedroom cottage near Robertsbridge with private garden, woodland views and access to two lakes; walking distance to a pub.

🛏️ 1 bed 👥 Sleeps 3 🐾 Pets welcome
Cottage
Stable Cottage from £463

Rother · 2.6 miles away

Stable Cottage

One-bedroom converted stable near Winchelsea, surrounded by Sussex woodland and countryside, with parking and a private garden.

🛏️ 1 bed 👥 Sleeps 2 🐾 Pets welcome
Cottage
The Blue Loft from £917

Rother · 2.6 miles away

The Blue Loft

The Blue Loft, Rother: detached two-bedroom cottage with direct access to Romney Marsh countryside, Rye and the Sussex coast.

🛏️ 2 beds 👥 Sleeps 4
Cottage
Pond Cottage from £447

Rother · 2.9 miles away

Pond Cottage

Two-bedroom detached barn on a working farm in an Area of Outstanding Natural Beauty, with two bathrooms and parking for two cars.

🛏️ 2 beds 👥 Sleeps 4
Cottage
Bramley Cottages - Blenheim Cottage from £571

Rother · 3.1 miles away

Bramley Cottages - Blenheim Cottage

Two-bedroom cottage on a working farm in the Tillingham Valley, with coastal walks and Rye nearby.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
Cottage
Holly Cottage from £967

Rother · 3.2 miles away

Holly Cottage

Four-bedroom cottage near Hastings with countryside views, a mile from the beach and local pubs, sleeps 9.

🛏️ 4 beds 👥 Sleeps 9
Cottage
The Wagon Lodge from £821

Rother · 3.3 miles away

The Wagon Lodge

The Wagon Lodge, Rother: four-bedroom cottage on a working farm with decking on two sides and a pond to explore.

🛏️ 4 beds 👥 Sleeps 8 🐾 Pets welcome
Cottage
The Beach House from £747

Rother · 3.5 miles away

The Beach House

Two-bedroom coach house in Rother, steps from Camber Sands beach with free parking and one pet welcome.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
Cottage
Benchwood House from £1,320

Rother · 3.6 miles away

Benchwood House

Two-bedroom house in Rother with woodland grounds, firepit and summerhouse, near Rye and Hastings.

🛏️ 2 beds 👥 Sleeps 4
Cottage
Shepherd’s Cottage from £907

Rother · 3.6 miles away

Shepherd’s Cottage

18th-century stable cottage for two on a working farm near Rye, with countryside views and easy beach access.

🛏️ 1 bed 👥 Sleeps 2
Cottage
Dory from £677

Rother · 3.6 miles away

Dory

Dory, 2-bed coastal cottage in Rother with a full kitchen, wood burner and enclosed garden; one dog welcome.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
Cottage
Saltmarsh Cottage from £707

Rother · 3.6 miles away

Saltmarsh Cottage

Saltmarsh Cottage, Camber Sands: two-bedroom coastal home for families and small groups, steps from the beach.

🛏️ 2 beds 👥 Sleeps 4
Pickdick Stable from £497

Rother · 3.7 miles away

Pickdick Stable

One-bedroom converted stable near Rye, with parking and private terrace in woodland setting.

🛏️ 1 bed 👥 Sleeps 2
Saunders Oast Barn from £961

Rother · 3.7 miles away

Saunders Oast Barn

Saunders Oast Barn, Hastings: converted 1860s barn sleeping 9 with three ensuite bedrooms, 3 miles from the coast.

🛏️ 3 beds 👥 Sleeps 9 🐾 Pets welcome
Cottage
Appletree Cottage

Rother · 4.1 miles away

Appletree Cottage

Grade II listed cottage near Rye with inglenook fireplace, sleeps 4, on the edge of Peasmarsh village in East Sussex.

🛏️ 2 beds 👥 Sleeps 4
Cottage
Sea Escape from £447

Rother · 4.3 miles away

Sea Escape

Sea Escape, Camber: two-bedroom ground-floor lodge where one dog stays free, metres from the beach.

🛏️ 2 beds 👥 Sleeps 4 🐾 Pets welcome
Cottage
Sussex Park

Rother · 4.3 miles away

Sussex Park

Three-bedroom holiday caravan in Camber with ground-floor living, parking for two cars, and the coast within a mile.

🛏️ 3 beds 👥 Sleeps 8
Riverside from £891

Rother · 4.7 miles away

Riverside

Three-bedroom riverside pub accommodation in Rotherham with balcony overlooking the water and parking on site.

🛏️ 3 beds 👥 Sleeps 6 🐾 Pets welcome
Cottage
Thornsdale Oast from £1,256

Rother · 4.9 miles away

Thornsdale Oast

Thornsdale Oast, Rother: five-bedroom detached house sleeping 10, one dog welcome, surrounded by walking country.

🛏️ 5 beds 👥 Sleeps 10 🐾 Pets welcome
🏡

Know a cottage in Winchelsea that's missing?

Run one yourself or know a good one? Suggest it and we'll review it for the site. Listings are free.

Add a cottage