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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Winterborne Monkton holiday rentals

A cozy living room with a grey sofa, a green throw blanket, and a dining area with wicker chairs.

1. 2 Bathsheba Terrace

2 Bathsheba Terrace
3.0 star property
Dorchester
10.0 out of 10, Exceptional, (2 reviews)
"Everything was there that we needed. It was clean, well laid out and comfortable. "
Canada
Rachael
The price is 12.886.977 ₫
15.464.372 ₫ total
includes taxes & fees
30 Oct - 31 Oct
2 Bathsheba Terrace
A modern living room with a wooden staircase, a flat-screen TV on a wooden stand, a cozy sofa, and a window with a view.

2. Walkersbase Nutallergy Friendly - Sleeps3 - Petsok

Walkersbase Nutallergy Friendly - Sleeps3 - Petsok
3.0 star property
Bridport
The price is 2.362.900 ₫
4.902.910 ₫ total
includes taxes & fees
4 Nov - 5 Nov
Walkersbase Nutallergy Friendly - Sleeps3 - Petsok
A modern living room with a sofa, coffee table, and a kitchen area with a washing machine.

3. Streamside Apartments

Streamside Apartments
3.5 star property
Yeovil
10.0 out of 10, Exceptional, (37 reviews)
"Excellent accommodation!"
Norway
Anonymous traveller
The price is 3.790.287 ₫
3.790.287 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Streamside Apartments
A grassy area with a view of a calm body of water and distant landforms.

4. Lobster Cottage

Lobster Cottage
3.5 star property
Rodwell
10.0 out of 10, Exceptional, (2 reviews)
"The property was clean and included everything you would need. The outside space was disappointing as it was just a table and chairs in a small concrete space rather than what is shown on the pictures depicting the outside space. The location made ot easy to score with a few shops, pubs and places near by."
United Kingdom
Sharon
The price is 14.556.426 ₫
17.467.711 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Lobster Cottage
A covered outdoor seating area with wicker furniture and a potted plant.

5. Cabin Sleeps 8 - Free Parking, Patio, Pool

Cabin Sleeps 8 - Free Parking, Patio, Pool
3.0 star property
Poole
The price is 3.669.687 ₫
6.057.568 ₫ total
includes taxes & fees
3 Nov - 4 Nov
Cabin Sleeps 8 - Free Parking, Patio, Pool
A harbor with boats docked, a building labeled 'The George Inn', and a cloudy sky.

6. Brewery View

Brewery View
2.0 star property
Rodwell
10.0 out of 10, Exceptional, (1 review)
"Very clean, location great, comfortable and we received regular updates and communication. All very helpful"
United Kingdom
Helen
The price is 13.238.440 ₫
15.886.128 ₫ total
includes taxes & fees
24 Oct - 25 Oct
Brewery View
A room with a large window overlooking a beach, a stone wall, and a small white table.

7. Weymouth Bay Apartment C

Weymouth Bay Apartment C
3.5 star property
Greenhill
10.0 out of 10, Exceptional, (1 review)
"Awesome morning earky dips into sea even if 10.5oc ..apartment very close for hot tea and shower..weymouth beach walking along kings beach lovely into town shops 15min or very slow paced 45mins beach combing...bowleazes walking along beach opp way to prestons fiishships mealout very tasty ..staring at the sea starring at the skys hofizons yachts tjme stopped perfect days..☀ 🛳 🌊 "
United Kingdom
STEVEN
The price is 19.330.466 ₫
23.196.559 ₫ total
includes taxes & fees
14 Nov - 15 Nov
Weymouth Bay Apartment C
A residential property with a patio, a sliding glass door, and a brick exterior.

8. Cedar Drive

Cedar Drive
2.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"So clean I could roll around in the property, also very thoughtful of the host, even a fly squatter was available. Would highly recommend if you’re in the area."
United Kingdom
David
The price is 14.995.755 ₫
17.994.906 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Cedar Drive
A stone staircase leading to a patio area with a view of a well-maintained lawn and a stone wall.

9. Badbury Lodge

Badbury Lodge
2.5 star property
Rodwell
10.0 out of 10, Exceptional, (1 review)
The price is 15.493.661 ₫
18.592.393 ₫ total
includes taxes & fees
24 Oct - 25 Oct
Badbury Lodge
A wooden deck with a pergola, a table with chairs, and a brick pathway.

10. Home Waters

Home Waters
3.5 star property
Wyke Regis
10.0 out of 10, Exceptional, (1 review)
The price is 17.807.459 ₫
21.368.951 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Home Waters
A row of colorful beach huts numbered 16 to 17, with a gravel path in front.

11. Bay Cottage

Bay Cottage
3.0 star property
Rodwell
10.0 out of 10, Exceptional, (1 review)
"Great location, thank you we enjoyed our stay"
United Kingdom
Neil
The price is 30.053.713 ₫
36.064.456 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Bay Cottage
Dining

12. Anchor Cottage

Anchor Cottage
3.0 star property
Weymouth Town Center
10.0 out of 10, Exceptional, (1 review)
"Very nice cottage. Very clean, and a lovely stay."
United Kingdom
Carolyn
The price is 13.589.903 ₫
16.307.884 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Anchor Cottage
A coastal beach with a prominent rock arch formation, sandy shores, and cliffs.

13. Agua de Plata, 26 Wakeling Island, Silverlake

Agua de Plata, 26 Wakeling Island, Silverlake
3.0 star property
Dorchester
9.0 out of 10, Wonderful, (2 reviews)
"It was amazing Anyone who travels to this part of the country needs to stay here It was beyond our expectation"
United Kingdom
barry
The price is 23.723.753 ₫
28.468.504 ₫ total
includes taxes & fees
30 Oct - 31 Oct
Agua de Plata, 26 Wakeling Island, Silverlake
A waterfront with several boats docked, a row of buildings with various businesses, and a clear sky.

14. Day Cottage

Day Cottage
3.0 star property
Weymouth Town Center
10.0 out of 10, Exceptional, (1 review)
"The cottage was absolutely excellent , clean, had everything you need,cosy, couldn’t ask for more ,also not far from the beach "
United Kingdom
Cindy
The price is 11.539.702 ₫
13.847.642 ₫ total
includes taxes & fees
16 Nov - 17 Nov
Day Cottage
A red brick building with a sign reading "BREWERS QUAY" and a glass-fronted structure adjacent to it.

15. Admiral's Quarter Apartment 5

Admiral's Quarter Apartment 5
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"Ideally placed to have a stroll to the harbour with the convenience of secure parking within the gated community. Within easy reach of pubs/restaurants (try the burgers at the Northe tavern 100 yards away) but a quiet area. It's in a residential block, most of residents friendly but there are rules on no ball games or storing of fishing rods/beach equipment outside of apartment to keep area clear. Designated space for car, big enough for my range rover, even though 1 neighbour came and checked...
United Kingdom
Richard
The price is 13.502.037 ₫
16.202.444 ₫ total
includes taxes & fees
30 Oct - 31 Oct
Admiral's Quarter Apartment 5
A two-story house with a white exterior, a stone wall on the right, and a small garden with potted plants and flowers.

16. The Little Cottage

The Little Cottage
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"Clean cottage, great location, comfortable beds."
Australia
Lea
The price is 16.694.493 ₫
20.033.392 ₫ total
includes taxes & fees
28 Oct - 29 Oct
The Little Cottage
Property grounds

17. Hide-a-way

Hide-a-way
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (2 reviews)
"It was in a peaceful location, although a bit far for walking into town. But the facilities were spot on, though there is no oven to cook proper meals. For someone who needs a quiet, chilled out, restful timeout, it is the perfect place to stay."
United Kingdom
Kim
The price is 11.920.454 ₫
14.304.545 ₫ total
includes taxes & fees
24 Oct - 25 Oct
Hide-a-way
A bedroom with a bed, a radiator, a fireplace, a wardrobe, and a painting on the wall.

18. Wey Cottage

Wey Cottage
3.5 star property
Rodwell
8.0 out of 10, Very good, (1 review)
"Good stay in good location for harbour."
United Kingdom
Kim
Wey Cottage
A red door with the number 29, a white doorbell, and a sign for 'Seagulls & Chips' on the wall.

19. Seagull and Chips

Seagull and Chips
2.0 star property
Weymouth Town Center
10.0 out of 10, Exceptional, (1 review)
The price is 12.359.783 ₫
14.831.740 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Seagull and Chips
A marina with multiple sailboats docked along a waterfront promenade.

20. Harbour Reach 7

Harbour Reach 7
2.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"They should state there’s not drying machine but besides that it was an amazing stay. My group and I really enjoyed the place as well as the local area. Excellent experience overall, and I think this place made our first international trip very enjoyable."
United States
Austin
The price is 16.548.050 ₫
19.857.660 ₫ total
includes taxes & fees
28 Oct - 29 Oct
Harbour Reach 7
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winterborne Monkton Hotel Reviews

Sleeping Bear Hotel Dorchester

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."
Alan Peter 3-night trip
Posted 13 hours ago
Sleeping Bear Hotel Dorchester

Frequently asked questions

Can I find a holiday rental in Winterborne Monkton?

Yes, there are holiday rentals close to the most popular sights in Winterborne Monkton, or you can select a more secluded option if you're looking for a relaxing stay.

What can I see and do in Winterborne Monkton?

While exploring the area, visit family-friendly sights like Abbotsbury Swannery, or get outside and enjoy nature at Dorset National Landscape. In the wider area, you’ll find Maiden Castle and Tutankhamun: The Exhibition.

What are holiday rentals like in Winterborne Monkton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winterborne Monkton. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for family trips.