Guesthouse vacation rentals in Weymouth and Portland District

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Top-rated guesthouse rentals in Weymouth and Portland District

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Guest favorite

Guesthouse in Dorset

4.84 out of 5 average rating, 122 reviews

Cosy garden cabin in the centre of Wareham

Quiet & cosy cabin with own bathroom within Wareham walls hosted by a Tibetan & English couple. A good place to explore the Jurassic coast & attractions such as Durdle Door, Lulworth Cove, Corfe Castle, Studland, Swanage, Arne Bird Sanctuary, Monkey World, Bovington Tank Museum & Wareham Forest. 5-minute walk to the picturesque quay & town centre which has pubs, restaurants, cafes, supermarkets, buses to tourist attractions & a cinema. 10-minute walk to station. Parking on available on drive.

Dec 7 – 14

R1,136 ZAR per night

Guest favorite

Guesthouse in Moreton

4.91 out of 5 average rating, 103 reviews

Full use of facilities: hot tub/fire pit/sauna/bbq

Little Oakford is your peaceful haven 'Far from the Madding Crowd' in the heart of idyllic, rural Dorset! At the end of a lane and on the edge of woods, from where birdsong can always be heard and in which deer can often be seen, its large private garden & all its amenities, including covered hot tub, gazebo, fire pit & 5 (s)eating areas, are for your free & exclusive enjoyment. With its free parking, kitchen, steam shower, superfast WiFi, 4K TV & Netflix, it's perfect for business or pleasure.

Sep 30 – Oct 7

R2,845 ZAR per night

Guest favorite

Guesthouse in Taunton

4.98 out of 5 average rating, 158 reviews

Idyllic chalet retreat in Somerset countryside

Exclusive chalet 2 miles outside Taunton, in the Trull area. Separate bedroom with ensuite, modern kitchen, lounge area to relax in & private gated parking. Deck area for al fresco dining & access to a BBQ in the orchard. We invite you to stroll down to the orchard to collect freshly laid eggs from our chickens for your breakfast every morning. A real secret hideaway, don't tell too many ! @thechaletsomerset Please Note: I follow Airbnb's strict cleaning protocols after each guests checks out.

Feb 6 – 13

R1,716 ZAR per night

Guest favorite

Guesthouse in Dorset

4.96 out of 5 average rating, 113 reviews

Seaside studio cabin minutes from 'secret' beach

Tucked away up an unmade track & five minutes walk from a 'secret' local beach; Cove Cabin is a compact, stylish, private space; perfect for a couple or two companions. On the doorstep of lesser known beaches & gardens but not far from Weymouth's bustling scenic harbour & golden sands. Ideal stop off whilst walking the SW Coast Path. The perfect area for watersports, wild swimming, walking, mooching around the harbour & locality, sampling the local seafood & eateries & just simply relaxing.

Jul 7 – 14

R2,328 ZAR per night

Guest favorite

Guesthouse in Dorset

4.98 out of 5 average rating, 102 reviews

Palm Cottage

A good sized modern One bedroom garden annex only a short walking distance to local pub, take away, convenience store & hairdressers with a 20 minute walk into the Town Centre and Beach (£6 - £7 taxi ride) Weymouth is a very popular tourist attraction with numerous high end eating establishments, a superb beach and harbour which are particularly vibrant during the Spring and Summer months, a golf course and a railway station. Only 13 miles from the picturesque Lulworth Cove & Durdle Door

Sep 27 – Oct 4

R2,123 ZAR per night

Guest favorite

Guesthouse in Uplyme

4.99 out of 5 average rating, 216 reviews

Cosy Hygge Hideaway-perfect place to escape.

The Hygge Hideaway is inspired by Scandinavian simplicity and New England coastal charm. RETREAT, RELAX, RECHARGE With increased focus on mental wellbeing this is the perfect place to escape & switch off (digital detox - no WiFi/Live TV). LUXURIOUS COMFORT A Morsø wood burning stove, bath tub, walk-in shower, kingsize memory foam bed all ensure a relaxed & restorative stay. TRANQUIL SETTING & CONVENIENT LOCATION Surrounded by trees and alongside the River Lym Lyme Regis beach only 1 mile!

Feb 2 – 9

R3,464 ZAR per night

Guest favorite

Guesthouse in Chideock

4.92 out of 5 average rating, 278 reviews

A beautiful annex in the village of Chideock

This is a beautiful self contained annex with a large double bed. There is safe off road parking. We are a five minute drive from the historic market town of Bridport. A fifteen minute walk to Seatown beach or a five minute drive. All part of the famous Jurassic coast. This is a walker's paradise, with outstanding Dorset scenery and friendly people. In addition we can provide a beautiful dinner £20 per head, Gym £10 per hour and Sauna £10 per hour. Please ask before you come or upon arrival.

Apr 6 – 13

R2,153 ZAR per night

Guest favorite

Guesthouse in Dorset

4.89 out of 5 average rating, 107 reviews

Gordon Annexe Guest Studio

Relax with the whole family at this peaceful place to stay in a stylish, newly refurbished, self contained studio apartment, with off road parking and use of shared garden. Located in the heart of the Jurassic coast in an area of outstanding natural beauty and close to the south west coast path which makes it a great place to stay for the outdoors type. It is also a 25 minutes walkl to the vibrant market town Bridport. Renowned for its Arts & Culture, pubs and twice weekly antiques market..

Jan 31 – Feb 7

R2,168 ZAR per night

Guest favorite

Guesthouse in Dorset

4.98 out of 5 average rating, 186 reviews

34 Monmouth Beach

34 Monmouth Beach lies to the west of the historic Cobb in Lyme Regis. It is a beautifully finished and stylishly furnished wooden chalet right on the beach. Enjoy uninterrupted sea views from the generous wooden deck at the front of the chalet. There is parking behind the chalet and a ramped access. Our chalet is great for couples, small families, friends; it can sleep 4. Our change over days are Friday and Monday (though this listing may state Fridays only), check in 4pm, check out 10am.

Mar 21 – 28

R2,685 ZAR per night

Guest favorite

Guesthouse in Piddlehinton

4.97 out of 5 average rating, 164 reviews

The Yorkshireman @ Piddlehinton

We are so excited about our new conversion. Completely self-contained, it is a lovely, light, cosy open space with a well equipped kitchen, modern bathroom and a cool sleeping platform/mezzanine. Piddlehinton is a special place, 20 mins from the Jurassic Coast and 10 mins from Dorchester, in the renowned Piddle Valley, with beautiful walks, views and award winning pub, The Thimble Inn. We’re right next door if you need anything, but if you prefer your privacy, you can be totally separate .

Oct 16 – 23

R2,059 ZAR per night

Guest favorite

Guesthouse in Dorchester

4.97 out of 5 average rating, 274 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.

Sep 22 – 29

R1,611 ZAR per night

Guest favorite

Guesthouse in Winterborne Stickland

4.9 out of 5 average rating, 173 reviews

Pretty Self-Contained Thatched Annexe in Dorset

Rosebud is a beautiful little cottage! It is a part of a large 18th Century thatched cottage set in the heart of beautiful North Dorset countryside, ideal for a peaceful getaway for two people . We are approx. 30 minutes from the Purbecks and Poole. Rosebud is newly refurbished with all the facilities you should require during your stay with us. We are very happy to help with any local advice as we love this part of the world and are pleased to be able to share it with you.

Sep 5 – 12

R2,494 ZAR per night