Winterbourne Steepleton Holiday Rentals, Dorchester: Private House Rentals

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Our top choices for Winterbourne Steepleton hotels

A room with a purple sofa, a grey sofa, and a white table with a vase of flowers.

A hotel room with two beds, a desk, a chair, a fireplace, and a window with curtains.

A reception area with a fireplace, a mirror, and a bookshelf with books.

A cozy living room with a plaid sofa, a wooden side table, and a lamp.

1. Sleeping Bear Hotel Dorchester

Dorchester

Christopher

฿2,215

฿2,658 total

includes taxes & fees

15 Nov - 16 Nov

A restaurant with a large copper dome, wooden tables, and potted plants.

A bar area with a checkered floor, wooden staircase, and bar stools.

A view through a window with a book on a windowsill.

A bedroom with a large bed, a wooden nightstand, a chair, a TV, and a window with a view.

2. The Duchess of Cornwall Inn

Dorchester

Colin

฿2,558

฿3,070 total

includes taxes & fees

1 Nov - 2 Nov

A modern dining area with a round table set for six, large windows, and a view of the garden.

A courtyard with potted plants, a small table, and chairs.

A modern living room with a grey sofa, a wooden coffee table, and a decorative mirror on the wall.

A modern building with large glass sliding doors, a brick facade, and potted plants outside.

3. Bay Tree House

Dorchester

John

฿3,336

฿4,004 total

includes taxes & fees

28 Oct - 29 Oct

A balcony with a wicker sofa, a woven coffee table, and a large vase.

A cozy living room with a fireplace, a chandelier, and a large portrait.

A sunlit room with large windows overlooking a beach, furnished with yellow armchairs and a wooden table.

4. Moonfleet Manor

Weymouth

Andreea

฿5,182

฿6,218 total

includes taxes & fees

15 Nov - 16 Nov

A wooden table with a fruit basket, two glasses of champagne, and small white cups on a wooden board.

A well-maintained garden with neatly trimmed hedges and a traditional house with a sloped roof in the background.

A cozy living room with a brick fireplace, two armchairs, and a patterned sofa.

A dining table set with plates, glasses, and candles, with a fireplace in the background.

5. Yalbury Cottage

Dorchester

Ardyce

฿2,836

฿3,403 total

includes taxes & fees

3 Nov - 4 Nov

A neatly arranged bedroom with a bed, two bedside tables with lamps, a small side table, and a wardrobe.

A dining area with wooden tables and chairs, stone walls, and large windows.

A living room with a fireplace, blue patterned sofa, wooden coffee table, and a stone wall.

A window with a view of a road and greenery, a bench with cushions, and a floral valance.

6. The Heritage Bed & Breakfast

Weymouth

Carol

฿3,874

฿4,649 total

includes taxes & fees

20 Oct - 21 Oct

A coastal landscape with white cliffs and a sandy beach.

A spa and beauty reception area with a stone wall, a chandelier, and a reception desk.

A dining area with a table set for four, large windows, and a view of the garden.

A conference room with round tables, chairs, and a projector screen.

7. George Albert Hotel & Spa

Dorchester

Dean

฿3,522

฿4,226 total

includes taxes & fees

18 Oct - 19 Oct

A table with various bottles and glasses of drinks, including a raspberry liqueur, tonic water, pink grapefruit gin, and fever-tree tonic water, set outdoors with a green umbrella and a stone wall in the background.

A bar area with a brick wall, hanging pendant lights, and a counter with various bottles and glasses.

A stone building with two banners reading "The Frampton Arms" and "FREE HOUSE." There are windows, a red door, and a small garden area with plants.

A wooden play structure with a slide and climbing area.

8. The Frampton Arms

Dorchester

Robert

฿2,193

฿2,632 total

includes taxes & fees

15 Nov - 16 Nov

A cozy restaurant interior with a blue sofa, wooden tables, and chairs, and large windows offering a view of the city.

A hotel room with two beds, patterned pillows, a large wall mural, and bedside lamps.

A bar area with a wooden herringbone floor, bar stools, and a variety of bottles and glasses on the shelves.

A white brick wall, a window, and a table with a potted plant.

9. The Bull Hotel

Bridport

paul

฿3,831

฿4,597 total

includes taxes & fees

15 Nov - 16 Nov

An indoor swimming pool with a glass ceiling, clear poolside railing, and a no diving sign.

A bar area with a tap system, shelves of liquor bottles, and a display of beer taps.

A bar area with a wooden counter, two chairs, a wine glass, a bottle, and a vase with flowers.

An indoor patio area with a stone wall, a white fence, and a row of metal chairs.

10. Best Western Weymouth Hotel Rembrandt

Melcombe Regis

David

฿3,637

฿4,365 total

includes taxes & fees

8 Nov - 9 Nov

A traditional pub with a clock, wooden beams, and outdoor seating.

The Smugglers Inn with a traditional thatched roof, a visible clock, and a sign for Hall & Woodhouse.

A wooden tray with various tea and coffee products, including Twinings and Arriba brands, and Nescafe Gold packets.

A bathroom with a bathtub, toilet, and sink.

11. The Smugglers Inn

Weymouth

Mr C J

฿3,864

฿4,637 total

includes taxes & fees

15 Nov - 16 Nov

A terrace with wicker furniture and a table, overlooking a green landscape and the sea under a cloudy sky.

A coastal golf course with bunkers and a view of the sea.

A spacious living area with a dining table, chairs, a sofa, and a ceiling fan.

A coastal beach with cliffs and clear blue water.

12. Eype's Mouth Country Hotel

Bridport

Narinderjit

฿4,004

฿4,804 total

includes taxes & fees

2 Nov - 3 Nov

A cozy room with a stone fireplace, a dining table with chairs, and a wicker basket.

A garden entrance with a pergola covered in grapevines, a pathway leading to a building, and a metal gate.

A narrow stone pathway leading to a traditional stone house with a thatched roof, surrounded by lush greenery and a small waterway.

A bedroom with a bed, a nightstand, a lamp, a wardrobe, a window, and a suitcase.

13. Greyhound Inn

Dorchester

Kathryn

฿4,449

฿5,339 total

includes taxes & fees

16 Oct - 17 Oct

A building with a green door and a sign that reads "DRIFTWOOD BED & BREAKFAST".

A mirror with a wooden frame mounted on a wall.

A kitchen with a green countertop, a coffee machine, and jars of spices.

A room with a dark blue sofa, a green and white striped pillow, and a wooden dresser.

14. Driftwood B&B

Westham

Andrew

฿2,443

฿2,443 total

includes taxes & fees

15 Nov - 16 Nov

A stone building with a garden patio featuring a table and chairs, a door, and a window with lights.

A stone house with a thatched roof, ivy-covered walls, and a blue door.

A pathway flanked by lush greenery and vibrant flowers, leading to a rustic archway.

A room with a glass door leading to a pool area, a clock on the wall, and exercise equipment.

15. Summer Lodge Country House Hotel

Dorchester

stefania

฿10,195

฿12,235 total

includes taxes & fees

16 Oct - 17 Oct

An outdoor seating area with wicker furniture and potted plants, a building with a balcony, and a clear sky.

A modern bathroom with a freestanding bathtub, a toilet, and a sink.

A hotel corridor with a red carpet, stone walls, and leather armchairs.

A bar area with a variety of bottles and glasses, leather chairs, and a dining area with tables and chairs.

16. Haddon House Hotel

Bridport

Kevin

฿4,793

฿5,752 total

includes taxes & fees

15 Nov - 16 Nov

A hotel room with two beds, a large window with curtains, and a view of a cityscape.

A harbor with multiple boats and a distant shoreline.

A stone building with a sign reading "HOTEL AQUA" and a list of amenities including boats, shop, cafe, air, nitrox, trinity, and mooring.

A bathroom with a window, a sink, and a toilet.

17. The Aqua

Portland

John

฿4,516

฿5,419 total

includes taxes & fees

29 Oct - 30 Oct

A beach with a statue, people, and buildings in the background.

A hotel room with two beds, a desk with a mirror, a television, and a window with curtains.

A breakfast buffet with various food items and beverages.

A two-story building with a sign reading "Alexandra" above the entrance. There are outdoor seating areas with tables and chairs.

18. Alexandra Hotel

Weymouth Town Center

sheelagh

฿2,682

฿3,218 total

includes taxes & fees

15 Nov - 16 Nov

A table with a view of a beach and the Olympic rings sculpture.

A coastal landscape with a natural rock arch formation, a sandy beach, and grassy cliffs.

A hotel sign with "The Heights Hotel" and a "Welcome" sign below it.

A restaurant with a view of the water, wooden tables and chairs, and a modern interior design.

19. Heights Hotel

Portland

Jean

฿4,247

฿5,097 total

includes taxes & fees

15 Nov - 16 Nov

A window with binoculars and a mug on the windowsill, overlooking a beach with waves and a cloudy sky.

A dining area with a table set for four, a view of the street with parked cars, and a sign advertising vacancies in en-suite rooms.

A room with a bed, two wicker chairs, a small table with a glass, and a view of the sea through a bay window.

A row of colorful Victorian-style buildings with bay windows and a pub sign.

20. Channel View Guest House

Weymouth Town Center

Anthony

฿3,819

฿4,582 total

includes taxes & fees

21 Oct - 22 Oct

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Top Winterbourne Steepleton Hotel Reviews

The Manor Hotel by Greene King Inns

8/10 Good

"Great for a quick one night stop. Staff all friendly"

Durdle Door Hotel

10/10 Excellent

"Excellent location for walking to Durdle Door and beyond. Close to local pubs and restaurants. Staff are very helpful and knowledgeable. Clean and tidy bedrooms. Discounted parking across the road. Visited in late September so wasn’t too busy."

Crown Hotel

10/10 Excellent

"An excellent venue for staying in the Blandford Forum area. Comfortable room with everything we needed. 10/10 breakfast ."

The Duchess of Cornwall Inn

10/10 Excellent

"Lovely clean large room. Great tv with a superb picture. Plenty of tea / coffee and biscuits welcome tray. We were surprised how quiet our sleep was, the pub below was busy but no sound from it. The decoration of the whole venue is incredible with so much to look at. There is a lot of car spaces but the area is very busy so it’s a bit of a search to find one."

Half Moon, Sherborne by Marston's Inns

8/10 Good

"A hotel above the pub it was surprisingly quiet but it was a Wednesday night. Lovely room, not brand spanking new but clean and functional. Lovely Phillips telly. Had to go to bar to get staff to do hotel tasks. Great stay 4/5."

The Bull Hotel

8/10 Good

"Late online-booking led to some issues with the location end parking nearby. Which was professionally and friendly solved by the staff. The room was rather small for two. Though the bathroom was OK and clean. The hotel has an historical flair and still many original features. Breakfast was plenty een very good. We stayed for one night."

The Jubilee Hotel West- with Spa Facilities

10/10 Excellent

"The room was a good size, we had a family room for 5. The room was clean and tidy and good amenities in the room itself. The best aspect was the seaview which was fantastic helped by some good October weather. We didn't use the bar much as we were visiting relatives who live in Weymouth - but it looked good with plenty to do. The best thing about staying in the older hotels on the front is access to the beach/Weymouth centre, room size and view. Overall very happy with the hotel and the price. Would definitely stay again - thanks."

The Frampton Arms

10/10 Excellent

"The room was clean and comfortable. The shower pressure and temperature was fantastic. Staff helpful and cheerful Breakfast was great, with a good selection of meat, cheese,bread and cereals."

TheHillbrookSherborne

10/10 Excellent

"Great location and large clean and comfortable room"

More cheap stays in Winterbourne Steepleton

The Warehouse

South Street Yeovil England

฿1,952

฿2,342 total

18 Oct - 19 Oct

includes taxes & fees

8/10 Very good! (68 reviews)

Terrace Lodge

16 S Western Terrace Yeovil England

฿2,036

฿2,443 total

15 Nov - 16 Nov

includes taxes & fees

8.4/10 Very good! (96 reviews)

Old Ship Inn

High W St Dorchester England

฿2,113

฿2,536 total

18 Oct - 19 Oct

includes taxes & fees

Monkton Wyld Court

Elsdon's Ln Bridport England

฿3,298

฿3,957 total

15 Nov - 16 Nov

includes taxes & fees

8.6/10 Excellent! (13 reviews)

The West Bay Hotel

Station Road Bridport England

฿5,079

฿6,095 total

28 Oct - 29 Oct

includes taxes & fees

Eton House

38 Preston Rd Yeovil England

Get rates

7.8/10 Good! (21 reviews)

Frequently asked questions

Where is the best place to stay in Winterbourne Steepleton?

Located 17.2 mi (27.8 km) from the heart of Winterbourne Steepleton, The Royal Lion Hotel is a top choice for your stay, based on our traveller data. Two other choices for your stay in the area are Fairhaven Hotel and Best Western Weymouth Hotel Rembrandt. See all available top hotels, or vacation rentals in Winterbourne Steepleton.

If I need to cancel my hotel reservation in Winterbourne Steepleton, will I receive a refund?

Yes, most hotel bookings are fully refundable as long as you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you booked a non-refundable reservation, it may still be possible to cancel it and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Winterbourne Steepleton.

What are some hotels with pools in Winterbourne Steepleton?

Best Western Weymouth Hotel Rembrandt: Hotel located near Weymouth Beach. Provides a full-service spa, an indoor pool and a health club. View all hotels with pools in Winterbourne Steepleton.

How is it staying in Winterbourne Steepleton?

Those travelling to Winterbourne Steepleton will definitely enjoy the sights to see and things to do. In Winterbourne Steepleton, there are 5 hotels and other accommodation options to choose from. Find out more about Winterbourne Steepleton.

What is there to see in Winterbourne Steepleton?

Places to visit in the wider area include Abbotsbury Swannery, Tutankhamun: The Exhibition and Dorset and East Devon Coast. You'll also find Bowleaze Cove Beach and Weymouth Beach in the area. Take a look at what more there is to see and do in Expedia's Winterbourne Steepleton guide.

Find hotels in Winterbourne Steepleton from ฿2,342

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Winterbourne Steepleton

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Winterbourne Steepleton hotels

1. Sleeping Bear Hotel Dorchester

2. The Duchess of Cornwall Inn

3. Bay Tree House

4. Moonfleet Manor

5. Yalbury Cottage

6. The Heritage Bed & Breakfast

7. George Albert Hotel & Spa

8. The Frampton Arms

9. The Bull Hotel

10. Best Western Weymouth Hotel Rembrandt

11. The Smugglers Inn

12. Eype's Mouth Country Hotel

13. Greyhound Inn

14. Driftwood B&B

15. Summer Lodge Country House Hotel

16. Haddon House Hotel

17. The Aqua

18. Alexandra Hotel

19. Heights Hotel

20. Channel View Guest House

Top Winterbourne Steepleton Hotel Reviews

The Manor Hotel by Greene King Inns

Durdle Door Hotel

Crown Hotel

The Duchess of Cornwall Inn

Half Moon, Sherborne by Marston's Inns

The Bull Hotel

The Jubilee Hotel West- with Spa Facilities

The Frampton Arms

TheHillbrookSherborne

More cheap stays in Winterbourne Steepleton

The Warehouse

Terrace Lodge

Old Ship Inn

Monkton Wyld Court

The West Bay Hotel

Eton House

Frequently asked questions

Go further with the Expedia app