Guest house holiday rentals in Weymouth and Portland District

Cosy Couples Hideaway with Hot Tub

The Annexe is a private guest retreat, exclusively for visitors with just yourselves on the property. Relax in your own charming garden with a covered hot tub and festoon lights – the perfect place to unwind after exploring Dorset’s stunning coastline, Durdle Door or the New Forest. Just a short walk from pubs, restaurants & shops, it’s an ideal base for your stay. Guests enjoy Sky Sports, Wi-Fi & a cosy outdoor seating area, making it perfect for a romantic, relaxing or adventure-filled stay

Garden Cottage, glorious Somerset countryside

Nestled in the grounds of Tarqua House in this idyllic village. Come and stay in our cosy hideaway on the Somerset/Dorset boarder close to the Jurassic Coast. A newly converted, self-contained cottage with exposed beams and underfloor heating. Super comfy kingsize double bed with mattress topper, White Co linen and towels. Fully equipped kitchenette including Smeg kettle and toaster, Nespresso coffee machine. Roberts Radio, Smart TV, Wifi. Outside space and parking. Great pub in the village.

Stunning and luxurious Manor House holiday home

This immaculate and luxurious ground floor expansive accommodation is light, airy, stylish and oozes opulence! Perfect for family, friends with a love for activities and exploring South Dorset. 10 minutes drive from Weymouth beaches, Lulworth Cove. Open plan kitchen to living area, two bedrooms, wet room, utility area, cloakroom, outstanding Orangery with garden views, private walled rear garden , enclosed coach house/ own drive in private grounds of Manor House, with direct countryside walks.

The Retreat ~ Hot Tub~ Sauna ~ Charming & Cosy Gem

Step into the stylish and comfortable 1BR 1Bath guest house nestled in the picturesque village of Tarrant Gunville. It offers a relaxing oasis with a luxury hot tub, sauna, and a perfect base to explore natural attractions and historical landmarks of Dorset County. Modern design and a rich amenity list will satisfy your every need. ✔ Comfy BR with a Double Bed ✔ Bright Living Space ✔ Kitchenette Amenities ✔ Garden ✔ Hot Tub ✔ Sauna ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Free Parking See more below.

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.

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

The Yorkshireman @ Piddlehinton

We are so excited about our 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 our award winning pub, The Thimble Inn. We are right next door if you need anything, but if you prefer your privacy, you can be totally separate.

The Perk Inn, Cosy & Secluded Garden Lodge

Welcome to The Perk Inn, a private and secluded garden lodge located in the central area of Broadstone, Poole in Dorset. Nestled within the garden of the owners' home, the space features a cosy double bedroom, modern shower room, an open plan kitchen/living room and a fenced courtyard where you can enjoy a morning coffee or an evening drink. Just a short walk to local shops, restaurants and transport links, The Perk Inn is the ideal relaxing base for exploring Dorset and surrounding areas.

Cosy Countryside 2-Bedroom Guest House

Escape to our cosy countryside annexe in Child Okeford within walking distance to historic Hambledon Hill. Set beside a peaceful stream with woodland views and birdsong, it’s perfect for a rural getaway. The self-contained space has 2 bedrooms (one with cot), a fully equipped kitchen for home cooking, and a shower room with washer and dryer. Enjoy the wood fire, private deck with grill, village shop and pubs. A peaceful home away from home to unwind and explore the charm of rural Dorset.

The Retreat

Welcome to your perfect hideaway! Tucked away in a quiet corner of our property, this self-contained annex is full of charm and style - ideal for solo travelers, couples, or remote workers looking for peace and inspiration. Thoughtfully designed with cozy, modern touches. Whether you stay here for a weekend escape or a longer stay, you'll love the calm atmosphere, natural light, and carefully curated decor. The Retreat is only a few minutes from local shops and sights!

Characterful 2-bedroom cozy cottage with garden

Enjoy a stylish experience at this cozy, centrally-located cozy two-bedroom cottage with modern facilities plus Sky, coffee machine and private garden. Bedroom one has a double bed, bedroom two is a twin with two single beds. Walking distance from shops, cafes, Church Ope beach, cliff paths. Visit Portland to sail, dive, rock climb, bike ride, hike, visit art exhibitions, relax and explore. Unsafe for pre-school kids. Sorry no under 4 years old . No smoking 🚭

The Penthouse (Small but mighty)

Enjoy a stylish experience at this centrally-located place on the Isle of Portland. So many places to visit and all within a stones throw away from our newly refurbished Penthouse. Guest access- just off the road down a private drive with one parking space directly outside. The space- One small but stylish room with a double bed and luxury bedding. Mini fridge and kettle. En-suite modern bathroom, towels included. Check-in from 16:00pm Check out before 10:00am