Vacation rentals in Winterborne Monkton

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winterborne Monkton

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Guest suite in Portesham

4.83 out of 5 average rating, 162 reviews

Modern living in a Traditional quaint village.

A self contained house attached to owners property. Access via secure garage and own door. Offering privacy in beautiful countryside at the edge of the village with pub/ cafe and shop. Open plan living space with TV/DVD player and log burner for the colder months. Dishwasher and washing machine in the property. 1 Bedroom with sloping ceiling with double or twin beds. Can also accommodate 1 baby (under 2 years to share bedroom). Bathroom with bath and shower. Own small garden with patio area.

Jun 15 – 22

G$20,706 GYD per night

Guest favorite

Cottage in Dorset

4.94 out of 5 average rating, 209 reviews

Little Barn is a cosy dwelling in a remote valley

Little Barn is located in a remote valley between Upwey and Portesham near Weymouth in Dorset A converted Barn with a modern open plan interior. An adequate garden with Outdoor furniture and BBQ with an external secure store for bicycles etc. The area is good for walking (dogs welcome), many footpaths line the surrounding countryside. Hardy's monument is situated a few miles away. The area offers good cycling both on and off road. Good access to the Dorset coastline which is a short drive away.

Aug 6 – 13

G$73,739 GYD per night

Guest favorite

Tiny home in West Stafford

4.92 out of 5 average rating, 195 reviews

The Old Reading Room West Stafford

The Victorian Reading Room of West Stafford is of historical importance. Used before the war as a Reading Room for the villagers and estate workers, the newspapers were provided, the village shop in the late 1930s, then a workshop and a store room for the church. We have now lovingly restored, decorated and furnished this amazing building into a cosy self catering holiday retreat, "far from the madding crowd" Open plan, comfy double sofabed, wood burner, country walks and fabulous village pub.

Feb 15 – 22

G$35,395 GYD per night

Guest favorite

Guest suite in Sutton Poyntz Weymouth Dorset

4.91 out of 5 average rating, 114 reviews

Private Guest Suite in Sutton Poyntz + own parking

We are a Modern Stone built cottage in beautiful village. Private secure gated parking for 2 guest cars. We love our local pub The Springhead which is 1 minute walk away, set around a duck pond with willow trees. There are numerous country and coastal walks nearby and we welcome dogs. We live upstairs but you are completely separate to us and left alone. There is 2 large bedrooms a kitchen equipped with small mini oven and microwave, bathroom inc bath and shower and comfortable lounge.

Jun 11 – 18

G$31,350 GYD per night

Guest favorite

Guest suite in Dorset

4.92 out of 5 average rating, 124 reviews

Discover Little Drey: Your Perfect Getaway

At Little Drey, you'll find comfort, and warm hospitality, all while being conveniently close to Dorchester. A variety of restaurants, cafes, and shops are all within walking distance. Close to some of the best places to visit in Dorset, and within easy reach of famous beauty spots and amazing places to visit. Parking on property along with self-check-in, makes it super easy to have a relaxing, enjoyable break. Your host lives next door and is on hand to make your stay the best possible.

Oct 24 – 31

G$20,698 GYD per night

Guest favorite

Shepherd’s hut in Martinstown

4.96 out of 5 average rating, 139 reviews

Cosy Shepherds hut near Dorchester

Nestled in a quiet wooded corner of our garden on the edge of the village of Martinstown. Fully self contained, the hut has everything you need inside and is in a great central location, close to Dorchester and just a short drive to Weymouth and Chesil beach. Fantastic walks, bike rides and lovely Jurassic coast beaches are nearby. We love to share our beautiful little corner of Dorset with both new guests and those of you have have stayed before. Check out our wonderful reviews!

Nov 17 – 24

G$25,080 GYD per night

Guest favorite

Guesthouse in Dorchester

4.97 out of 5 average rating, 273 reviews

Lovely, Quiet Studio Annex (with Netflix)

Self contained, self catering studio annex based in the county town of Dorchester. The annex is suitable for 2 adults (a z-bed can be supplied for 1 child under 12). The towns amenities are all within a short walking distance, including the new 'Brewery Square' development. Great base to explore Dorset's fabulous coast, countryside and walk in the footsteps of Thomas Hardy's Casterbridge. Motorbike friendly, high chair & travel cot available. Complimentary tea and coffee. Netflix TV.

Nov 27 – Dec 4

G$17,697 GYD per night

Guest favorite

Cottage in Lewell

4.94 out of 5 average rating, 244 reviews

Jasmine Cottage

Jasmine Cottage is a characterful, compact barn conversion, that sits next to the 400 year old farm house. It sleeps up to four people (including infants), with a double and a twin room. We are one mile away from The Wise Man Inn - an award-winning pub; 6 miles from Dorset's stunning Jurassic coast and 3 miles from the county town of Dorchester. You will, however, need a car- or bikes! Sorry, no pets and no smoking. No EV charging, yet, but there are many fast charging points nearby.

Nov 7 – 14

G$35,734 GYD per night

Guest favorite

Guest suite in Long Bredy

4.92 out of 5 average rating, 140 reviews

Stylish hayloft conversion next to 18thC farmhouse

A newly converted hayloft set up as a one bedroom house. Pitched, beamed ceiling in bed/sitting room, own kitchen downstairs. Spacious shower room, separate small WC No TV but WiFi. Private entrance from village lane into property. In the heart of the Bride Valley so perfect for all year round walkers and nature lovers. Jurassic Coast 5 miles away. One of the richest areas in the UK for hill forts and ancient earthworks. Very houseproud so regrettably no pets and no smokers.

Mar 19 – 26

G$23,805 GYD per night

Guest favorite

Apartment in Chickerell

4.95 out of 5 average rating, 140 reviews

Little Knapp

In a designated area of outstanding natural beauty “Little Knapp” a modern coach house style self contained studio apartment is nestled within a private hamlet very close to all the amenities of Chickerell and within a five minute drive of the coastal resort of Weymouth. Situated on the famous Jurassic coast road and only a five minute walk to join the Jurassic South Coast foot path, “Little Knapp” is ideally placed for exploring the wonderful county of Dorset.

Apr 22 – 29

G$21,502 GYD per night

Guest favorite

Cottage in Dorset

4.98 out of 5 average rating, 310 reviews

The Condo (Indoor Pool available May-Oct only)

Self contained detached cottage in a tranquil location close to the famous 'Jurassic Coast' ; Durdle Door, Lulworth, Corfe Castle, Weymouth and Dorchester are all a short drive away. Further attractions close by are Monkey World, Bovington Tank Museum, and Sculpture by the lakes. There is a well stocked village shop and good village pub. Dorset has so much to offer, with beautiful coastline and breathtaking scenery. Relax in the pool at your leisure!

Dec 2 – 9

G$26,546 GYD per night

Superhost

Home in Dorset

4.83 out of 5 average rating, 186 reviews

Beautiful townhouse in centre of Dorchester

This townhouse is ideally located in the heart of the historic town of Dorchester - just a 2 minute walk from the shops, restaurants, pubs and museums. This modern 3 bedroom house is suitable for couples and families. There is 1 bathroom and 2 shower rooms/ WCs, one of which is ensuite. There is a fully equipped kitchen and a large lounge / dining area. Please note, bedroom 3 is very small (4 ft bed). The property comes with one private parking space.

Jun 3 – 10

G$37,549 GYD per night