All Hotels by Freetobook in Winchester - 2026 Updated Prices

A large red brick building with a central entrance flanked by columns, a fountain in front, and trees on either side.

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Our top choices for Winchester Freetobook

A bedroom with a metal bed frame, a stone-patterned wall, a window with curtains, and a mounted fire alarm.

A rooftop terrace with tiled flooring, metal chairs, and round tables, each with a vase of yellow flowers.

A two-story building with a sign for 'The Black Hole Bar' on the ground floor.

A dining area with a checkered floor, a wooden table with a bowl and cutlery, a red polka dot tablecloth, and a shelf with kitchen items.

1. The Black Hole

Winchester City Center

VICTOR

£128

includes taxes & fees

26 Oct - 27 Oct

A bedroom with a large bed, wooden headboard, and a view of the outdoors.

A reception desk with a framed scheme, a bottle of lotion, and a notebook.

A cozy room with a brick fireplace, a yellow armchair, a small wooden table, and a woven pouf.

A bedroom with a large bed, a chair, a nightstand with a lamp, and a view of the garden through the window.

2. Cottage Lodge Hotel

Brockenhurst

Simon

£110

includes taxes & fees

20 Oct - 21 Oct

A covered patio area with wooden walls and large sliding glass doors.

A hallway with a staircase on the left, a door at the end, and a small table with items on the right.

A bedroom with a bed, bedside tables, a wardrobe, a chair, and a mirror.

3. Oak Tree Rooms

Brockenhurst

John

£88

includes taxes & fees

1 Nov - 2 Nov

A bedroom with a brick wall, a fireplace, a television, and two wicker chairs.

A corner room with two wicker chairs, a small round table, and a view of the street outside.

A two-story residential building with a corner bay window, a brick facade, and a white front door.

A dining area with a fireplace, wooden chairs, a table, and a chandelier.

4. The Caledon

Cowes

Glenn

£107

includes taxes & fees

19 Oct - 20 Oct

A stone pathway leading to a building with a red-tiled roof, surrounded by lush greenery and a variety of plants.

A modern kitchen with white cabinets, a microwave, and a stove. There is a grey sofa with a blanket, a wooden bench, and a TV on the wall.

A modern living room with a sectional sofa, a black coffee table, and a view of a garden.

A modern living room with a grey sofa, wooden desk, and a large mirror.

5. Hamble Retreat House and Luxury Studios

Southampton

Omar

A bedroom with a large bed, a nightstand, a chair, a window with curtains, a wall-mounted TV, and a ceiling light fixture.

A narrow street with The Union Inn, a traditional building with a signboard and a lamp post.

A bar area with a wooden counter, bar stools, and a red sign. There are bottles, glasses, and a cash register. The room has wooden beams and large windows.

A cozy room with a fireplace, vintage furniture, and a map on the wall.

6. The Union Inn

Cowes

Stuart

£97

includes taxes & fees

2 Nov - 3 Nov

A table set outdoors with a pitcher of orange juice, glasses, and a bottle.

A wooden dining table set with white cups, saucers, a teapot, and a tray with jars.

A window with a decorative valance and curtains, a view of an outdoor patio with a table and chairs, and a stone planter with plants.

A corner building with a green door, labeled "Britannia House," featuring a traditional brick facade and multiple windows.

7. Britannia House

Lymington

PAUL

A Victorian Lodge entrance with a dark blue door, two potted topiary plants, a small set of stone steps, and a traditional brick facade.

A modern kitchen with a microwave, stove, and cabinets.

A bedroom with a bed, a brown leather sofa, a painting on the wall, and a ceiling fan.

A compact, modern bedroom with a large bed, a small kitchenette, a seating area with a chair, and a view of the outdoors.

8. The Victorian Lodge

Ryde

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Top Winchester Hotel Reviews

ibis Southampton Centre

10/10 Excellent

"Great hotel with comfortable bed, nice breakfast and affordable price. This is like my secondary home."

Moxy Southampton

10/10 Excellent

"Lovely stay at this hotel, close to everything"

Novotel Southampton

10/10 Excellent

"Good location especially for the railway station. Good choice of food at breakfast."

Winchester Royal Hotel

10/10 Excellent

"Comfortable room and helpful staff"

The Winchester Hotel & Spa

10/10 Excellent

"Spa was amazing"

Harbour Hotel Southampton

8/10 Good

"Rooms don’t have safe, fridge nor coffee maker."

Days Inn by Wyndham Winchester M3

8/10 Good

"Perfect for a stopover. Small service area next door. Includes Burger King, M&S and smiths."

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Winchester Holiday Rentals

Room 1

Check prices for these dates

Our top choices for Winchester Freetobook

1. The Black Hole

2. Cottage Lodge Hotel

3. Oak Tree Rooms

4. The Caledon

5. Hamble Retreat House and Luxury Studios

6. The Union Inn

7. Britannia House

8. The Victorian Lodge

9. The Maples

10. Holly Tree House

Top Winchester Hotel Reviews

ibis Southampton Centre

Moxy Southampton

Novotel Southampton

Winchester Royal Hotel

The Winchester Hotel & Spa

Harbour Hotel Southampton

Days Inn by Wyndham Winchester M3

Explore a world of travel with Expedia

Search Hotels by Freetobook in Winchester from £88

Check prices for these dates

Our top choices for Winchester Freetobook

1. The Black Hole

2. Cottage Lodge Hotel

3. Oak Tree Rooms

4. The Caledon

5. Hamble Retreat House and Luxury Studios

6. The Union Inn

7. Britannia House

8. The Victorian Lodge

9. The Maples

10. Holly Tree House

Top Winchester Hotel Reviews

ibis Southampton Centre

Moxy Southampton

Novotel Southampton

Winchester Royal Hotel

The Winchester Hotel & Spa

Harbour Hotel Southampton

Days Inn by Wyndham Winchester M3

Explore a world of travel with Expedia