Winterborne Monkton Holiday Rentals, Dorchester: Private House Rentals

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Winterborne Monkton

Pet friendly

Apartment

Pool

Condo

Spa

Family friendly

Hot tub

Cottage

Waterpark

Cabin

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Winterborne Monkton hotels

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

A two-story building with a flag, windows, and a street in front.

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

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

1. Sleeping Bear Hotel Dorchester

Dorchester

Alan Peter

฿2,242

฿2,690 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

2. The Duchess of Cornwall Inn

Dorchester

Colin

฿2,697

฿3,236 total

includes taxes & fees

1 Nov - 2 Nov

A two-story building with a traditional architectural style, featuring a prominent sign for 'The George Red & Breakfast'.

A hotel room with a bed, a chair, a television, and a sliding glass door leading to an outdoor area.

A bedroom with a bed, a chair, a fireplace, and a mirror on the wall.

3. The George B&B

Melcombe Regis

Krisztina

฿3,491

฿4,189 total

includes taxes & fees

28 Oct - 29 Oct

An indoor swimming pool with a blue-tiled floor and a white fence.

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

A neatly made bed with white linens, a black headboard, and a bedside table with a lamp.

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

4. Best Western Weymouth Hotel Rembrandt

Melcombe Regis

David

฿3,674

฿4,409 total

includes taxes & fees

8 Nov - 9 Nov

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

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

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

A traditional thatched-roof cottage with brick walls, multiple windows, and potted plants.

5. Yalbury Cottage

Dorchester

Ardyce

฿2,865

฿3,438 total

includes taxes & fees

22 Oct - 23 Oct

A wooden play structure with a slide and climbing area.

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 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 modern bedroom with a large bed, two bedside tables with lamps, a desk with a chair, and a wardrobe.

6. The Frampton Arms

Dorchester

Robert

฿2,219

฿2,663 total

includes taxes & fees

25 Oct - 26 Oct

A bedroom with a white metal bed frame, a white upholstered chair, a bedside table with a lamp, and a window with curtains.

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

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

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

7. The Smugglers Inn

Weymouth

Mr C J

฿3,708

฿4,449 total

includes taxes & fees

25 Oct - 26 Oct

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

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.

A reception desk with a plant, a sign, and a stack of magazines.

8. Driftwood B&B

Westham

Andrew

฿2,458

฿2,458 total

includes taxes & fees

30 Oct - 31 Oct

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

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

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

9. Moonfleet Manor

Weymouth

Andreea

฿5,243

฿6,292 total

includes taxes & fees

5 Nov - 6 Nov

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

A bedroom with a sloped ceiling, a bed with orange bedding, a decorative pillow, and a wall with a jungle-themed wallpaper.

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

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.

10. Channel View Guest House

Weymouth Town Center

Anthony

฿3,857

฿4,629 total

includes taxes & fees

4 Nov - 5 Nov

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

A building with a sign reading "Alexandra" and a café bar sign below it.

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

A breakfast buffet with various food items and beverages.

11. Alexandra Hotel

Weymouth Town Center

sheelagh

฿2,698

฿3,237 total

includes taxes & fees

3 Nov - 4 Nov

A corner building with a white awning labeled "Timid."

A bedroom with a bed, two chairs, a nightstand, a lamp, and a window with curtains.

A marina with multiple sailboats docked, surrounded by terraced buildings.

Two patterned chairs facing a window with a checkered blind.

12. Timrick Lodge Hotel

Weymouth Town Center

Martin

฿2,266

฿2,719 total

includes taxes & fees

3 Nov - 4 Nov

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

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

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

A modern bedroom with a flat-screen TV, a round mirror, a dresser, and a small ottoman.

13. Bay Tree House

Dorchester

John

฿3,351

฿4,021 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 window with a view of a road and greenery, a bench with cushions, and a floral valance.

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

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

14. The Heritage Bed & Breakfast

Weymouth

Carol

฿3,714

฿4,457 total

includes taxes & fees

22 Oct - 23 Oct

A hotel room with two beds, a sofa, and large windows with curtains.

A hotel room with two beds, a sofa, a TV, and a balcony with a view of the sea.

A bar area with wooden paneling, a dog menu sign, and a patterned floor.

15. The Jubilee Hotel West- with Spa Facilities

Weymouth Town Center

Mihai

฿2,622

฿3,146 total

includes taxes & fees

22 Oct - 23 Oct

A bedroom with a bed, two bedside tables, a chandelier, and a geometric-patterned wall.

A garden with potted plants and a barbecue grill.

A building with a prominent sign reading "ASHMIRA."

A hallway with a chandelier, a staircase, and a door with frosted glass panels.

16. Ashmira Guest House

Greenhill

฿4,189

฿4,189 total

includes taxes & fees

3 Nov - 4 Nov

A hotel room with two beds, a desk, and a view of the sea.

A row of traditional terraced houses with a street in front.

A hot tub in a covered outdoor area with a stone wall and greenery.

A reception area with a wooden reception desk, a mounted star decoration, and a wall-mounted sign with guidelines.

17. The Jubilee Hotel East- with Spa Facilities

Weymouth Town Center

Sukhchain

฿2,569

฿3,083 total

includes taxes & fees

22 Oct - 23 Oct

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 restaurant interior with wooden tables and blue chairs, large windows with views, and a curved ceiling.

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

18. The Aqua

Portland

John

฿4,569

฿5,483 total

includes taxes & fees

29 Oct - 30 Oct

A view from a window overlooking a busy street with a beach and ocean in the background.

A beachfront apartment building with ivy-covered walls, outdoor seating, and a sign reading "BEACHVIEW APARTMENT".

A hotel lobby with a check-in desk, seating area, and large windows.

A breakfast buffet with various food items and condiments.

19. Fairhaven Hotel

Weymouth Town Center

Shaun

฿2,569

฿3,083 total

includes taxes & fees

25 Oct - 26 Oct

A bedroom with a large bed, a hanging chandelier, a wardrobe, a mirror, and a view of the outside through a window.

A modern kitchen with white cabinets, a stainless steel sink, and a tiled backsplash.

A harbor with boats docked, buildings along the waterfront, and a bird flying in the sky.

A modern kitchen with a sink, a dining area with a table, and a living room with a sofa.

20. St Johns Guest House

Weymouth Town Center

Paul

฿4,120

฿4,944 total

includes taxes & fees

22 Oct - 23 Oct

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Winterborne Monkton attractions

Maiden Castle

9.2/10 (9 reviews)

Enjoy spectacular views and discover fascinating history at one of England's largest Iron Age hill forts, home to temples, battlements and ancient burial sites.

See properties

Top Winterborne Monkton Hotel Reviews

Fairhaven Hotel

8/10 Good

"For some reason I could only rate 4*’s for each section when if allowed I would have marked the full 5, will definitely be going back to fair haven, lovely little find"

Lulworth Cove Inn

8/10 Good

"Lovely staff and very helpful beautiful room"

The Frampton Arms

8/10 Good

"Literally 5 m from the functional train rails. Train stops from 12 pm to 5:30 am. Pub music stops at 11 pm. Dinner was ok. We skipped breakfast due to amazing reviews. Pictures do not match the actual result."

The Manor Hotel by Greene King Inns

8/10 Good

"I will definitely stay here again. Great location, staff are superb and very friendly. Restaurant is really nice with plenty of menu choices. Only thing worth noting is the room I was in was adjoining on both sides and you hear everything if you are a light sleeper."

The Jubilee Hotel East- with Spa Facilities

8/10 Good

"Mattress bit worn could do with grab rail in shower cubicle but overall a pleasant stay. Very good food and good staff"

Durdle Door Hotel

8/10 Good

"Nice cozy place with a wonderful view. Staff super helpful and accommodating too."

Sleeping Bear Hotel Dorchester

10/10 Excellent

"Lovely place to stay, convenient for town and for visiting Dorsey County Hospital which was my main reason for visiting Dorchester."

Kingston Country Courtyard

10/10 Excellent

"Stunning views from the garden"

Crown Hotel

10/10 Excellent

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

More cheap stays in Winterborne Monkton

Terrace Lodge

16 S Western Terrace Yeovil England

฿2,060

฿2,472 total

8 Nov - 9 Nov

includes taxes & fees

8.4/10 Very good! (98 reviews)

Old Ship Inn

High W St Dorchester England

฿2,135

฿2,562 total

1 Nov - 2 Nov

includes taxes & fees

The Warehouse

South Street Yeovil England

฿2,262

฿2,715 total

25 Oct - 26 Oct

includes taxes & fees

8/10 Very good! (69 reviews)

Jurassic Bay Holidays

22 Ranelagh Rd Weymouth England

฿2,793

฿4,475 total

2 Nov - 3 Nov

includes taxes & fees

The West Bay Hotel

Station Road Bridport England

฿5,093

฿6,112 total

17 Nov - 18 Nov

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 Winterborne Monkton?

Fairhaven Hotel, located 5.8 mi (9.4 km) from the heart of Winterborne Monkton, is a top choice for your stay, based on our traveller data. Other good options for your trip to the area are Best Western Weymouth Hotel Rembrandt and Sleeping Bear Hotel Dorchester. See all available top hotels, or vacation rentals in Winterborne Monkton.

If I need to cancel my hotel reservation in Winterborne Monkton, will I receive a refund?

Yes, you'll find most hotel reservations are refundable if you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If your reservation is non-refundable, it may still be possible to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winterborne Monkton.

What is staying in Winterborne Monkton like?

Visitors to Winterborne Monkton will definitely find plenty to explore and enjoy. There are 2775 hotels and other accommodation options in the surrounding area. Find out more about Winterborne Monkton.

What is there to see in Winterborne Monkton?

A couple of favourite places to visit are Maiden Castle and Dorset National Landscape. You'll also find Tutankhamun: The Exhibition and Bowleaze Cove Beach in the area. Take a look at what more there is to see and do in Expedia's Winterborne Monkton guide.

Find hotels in Winterborne Monkton from ฿2,458

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Winterborne Monkton

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Winterborne Monkton hotels

1. Sleeping Bear Hotel Dorchester

2. The Duchess of Cornwall Inn

3. The George B&B

4. Best Western Weymouth Hotel Rembrandt

5. Yalbury Cottage

6. The Frampton Arms

7. The Smugglers Inn

8. Driftwood B&B

9. Moonfleet Manor

10. Channel View Guest House

11. Alexandra Hotel

12. Timrick Lodge Hotel

13. Bay Tree House

14. The Heritage Bed & Breakfast

15. The Jubilee Hotel West- with Spa Facilities

16. Ashmira Guest House

17. The Jubilee Hotel East- with Spa Facilities

18. The Aqua

19. Fairhaven Hotel

20. St Johns Guest House

Stay near popular Winterborne Monkton attractions

Maiden Castle

Top Winterborne Monkton Hotel Reviews

Fairhaven Hotel

Lulworth Cove Inn

The Frampton Arms

The Manor Hotel by Greene King Inns

The Jubilee Hotel East- with Spa Facilities

Durdle Door Hotel

Sleeping Bear Hotel Dorchester

Kingston Country Courtyard

Crown Hotel

More cheap stays in Winterborne Monkton

Terrace Lodge

Old Ship Inn

The Warehouse

Jurassic Bay Holidays

The West Bay Hotel

Eton House

Frequently asked questions

Go further with the Expedia app