Cottage holiday rentals in Weymouth and Portland District

A charming stone cottage is surrounded by lush greenery and various colorful flowering plants. A small white table and two chairs are placed outside, inviting guests to enjoy the garden view. The cottage features a traditional door framed by vibrant foliage.

4.97 out of 5 average rating, 691 reviews

Cute, Cosy & Stylish Bothy Cottage, near Sherborne

Stylish, Comfortable & Quirky - “Top 10 Dorset Airbnb” (Conde Nast Traveller) in a “Top 50 UK Village” (Sunday Times). The Bothy is a detached stone cottage where you can share some free Prosecco on your private terrace. It is in the rural historic Yetminster Conservation Area with a thatched pub, café & shop. It is next door to a quintessential "Chocolate Box" thatched cottage. You are on the edge of the Dorset Area of Outstanding Natural Beauty with good access to the sea & Jurassic Coast.

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4.93 out of 5 average rating, 233 reviews

The exterior features a traditional stone façade with a white front door labeled '10'. A window with sheer lace curtains is framed by a window box filled with pink and purple flowers, adding a touch of greenery to the entrance.

Cottage in Easton

1888 Portland stone cottage

1888 Portland stone cottage, with many original features. Stone fireplace with log burner. Cosy 2 bedroom, 3 storey cottage located within easy walking distance of Easton Square, which has local amenities, including grocery stores, chemist, pubs and cafes. Small sunny aspect courtyard with bistro table and chairs. A perfect holiday location all year round, for either sun and relaxation, or enjoy activities like windsurfing, sailing, diving, rock climbing, fishing, walking and bird watching.

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4.95 out of 5 average rating, 489 reviews

A cottage made of natural stone is surrounded by lush greenery and colorful flowers. A spacious balcony extends over the entrance, providing an outdoor area to enjoy the views. The sun illuminates the property, enhancing its inviting presence in the serene landscape.

Cottage in Morcombelake

Romantic hillside hideaway with outstanding views

A unique and romantic hideaway, Quarryman's Cottage is dinner on the roof terrace watching the sunset over Lyme Bay & Charmouth, stargazing from the luxury freestanding bath, epic views from the double shower, reading under the old oak tree, BBQ's & firepits, leisurely walks to The Anchor at Seatown via Golden Cap or the coastal path, the sound of birdsong, the glimpse of a deer, curling up in front of the wood burner in winter. It is a tranquil & heavenly escape from the bustle of daily life.

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Superhost

An indoor pool is surrounded by sleek gray tiling and illuminated by recessed lighting. The pool's inviting turquoise water reflects the ceiling lights. A cozy seating area with cushions is visible in the corner, providing a relaxed atmosphere.

Cottage in Osmington

4.85 out of 5 average rating, 200 reviews

A luxury unique home spa - White Stones Retreats.

Set in a prime position amidst a quintessential village of thatched cottages. Where wildflower paths and trickling streams amble down the the beautiful Osmington Bay. Toe dipping in the shallows, coastal walks under flaring sunsets, hibernating in our home spa while storms crash outside. Our unique holiday home offers a sanctuary in all weathers. With a collated & collected vibe, this light filled cottage is perfect for families looking for a beach escape, only a 5 minute drive to the sea.

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4.97 out of 5 average rating, 194 reviews

A bright living area features a comfortable sofa with navy blue and plaid cushions, complemented by a rustic coffee table. A flat-screen TV is mounted on the wall, and natural light floods in through large windows, illuminating the stone wall and wooden furniture.

Cottage in Weymouth

Cottage close to Beach & Old Harbour with Parking

Sydenham Cottage | Stylish Coastal Retreat with Parking | Walk to Beach & Harbour Beautifully refurbished to a high standard, Sydenham Cottage is a stylish and comfortable base for your Weymouth stay. Just a 2-minute walk from the bustling harbour and moments from the award-winning beach, it’s perfect for exploring cafés, restaurants, and the coast. Prices shown include Airbnb’s 18.6% booking fee. This property is also available to book on other platforms, where prices and fees may differ.

LocationFamilyParking

A modern kitchen features a wooden dining table surrounded by four woven chairs. A large range cooker is positioned against the tiled backsplash, with ample white cabinetry overhead and below. Open shelving displays glassware and decorative items, complemented by soft lighting and a neutral-colored floor.

4.95 out of 5 average rating, 245 reviews

Strawberry Cottage

Lovingly restored and modernised by Harry in 2011, Strawberry Cottage is nestled by the river Wey in the village of Upwey, Dorset. This quaint property is close to the famous Jurassic Coast, within 4 miles of the seaside town of Weymouth and Dorchester town.Durdle Door / Lulworth Cove is an approximate 29 minute drive,and the main supermarket is 8 minutes away by car. Upwey has two pubs a busy tearoom,garden nursery and Tesco Express all within 5 to 10 minutes walk. Relax inside or out.

LocationFamilyOutdoor spaces

4.91 out of 5 average rating, 264 reviews

A cozy lounge area features a rustic stone fireplace with a log burner, surrounded by soft seating. A plush rug lies on the wooden floor, and framed pictures are hung on the walls. A staircase leads to the upper level.

Cottage in Easton

Milly Moll Cottage, next to Church Ope Cove.

Julie and Matt welcome you to Milly Moll Cottage. A quirky C18th, grade 2 listed property full of character and charm, just next door to the Portland museum. Built of Portland stone with original fireplaces and a cozy lounge with a log burner, from here you can explore the Jurassic coast. It’s a 2 minute walk to Church Ope Cove, either passing under Rufus Castle arch or via the ruins of St Andrews church and is ideally placed for numerous outdoor pursuits. We hope you will enjoy your stay.

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4.94 out of 5 average rating, 103 reviews

Cobb Cottage - Harbourside, permit parking

Cobb Cottage is a stylish hideaway, tucked down a cobbled side street in the heart of Weymouth's historic harbour. The cottage has been lovingly converted from a former bookshop into a contemporary, centrally located holiday home with easy access to Weymouth harbour. Perfectly suited for two couples or a family, with three bedrooms and two bathrooms. There is a parking permit to for one car which provides free parking on street outside the cottage, or in a nearby car park. Dog friendly!

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A charming barn conversion features natural stone walls and large windows that invite ample sunlight. The surrounding landscape includes lush greenery and a clear blue sky, creating a serene rural atmosphere. The driveway leads to the entrance, providing easy access to the property.

4.8 out of 5 average rating, 202 reviews

Stunning Barn conversion with heated swimming pool

Courage Cottage is a two bedroom detached barn conversion in a Georgian farmyard.The barn was converted in 2013 so has all modern conveniences including underfloor heating. It is very individual and situated in a quiet , rural setting. It has two bedrooms with en-suite bathrooms. The village of Martinstown has an excellent pub and shop. Dorchester is 2 miles away and has every facility including good rail connections in all directions.Swimming pool (shared ) open May 15th-Sept 15th

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A charming harbourside cottage is viewed from across the water, showcasing a two-story facade with various window styles. A small boat is docked in the foreground, while the surrounding buildings exhibit a mix of soft colors and architectural features that complement the waterfront setting.

4.94 out of 5 average rating, 149 reviews

Harbour's Edge Cottage - Nothe Parade, Weymouth

Beautiful harbourside cottage with fantastic outlook onto Weymouth harbour. This two bedroom cottage is delightfully decorated and has everything you need for a wonderful vacation. The kitchen is really well equipped & there is a washer dryer. The dining area (ground floor) is great for an evening meal & there is a view of the harbour from many of the rooms. The lounge has amazing views of the harbour and is located on the first floor along with the twin bedroom and main bathroom.

FamilyValueLong stay

4.99 out of 5 average rating, 267 reviews

The exterior of the cottage is showcased, highlighting a charming wooden structure adorned with climbing foliage. A gravel driveway leads up to the entrance, framed by neatly arranged planters. A wooden fence enhances the privacy of the property, complemented by young trees.

Cottage in Bridport

Berry Farm Cottage

Berry Farm Cottage nestles in a private area of the grounds of Berry Farm, which dates back to the 16th century. It is located in the charming Conservation Village of Walditch, within walking distance of Bridport. The Cottage itself has 2 bedrooms and two bathrooms with an open-plan living space and is set away from the main house in its own private grounds, with 1,200sqm (0.3acres) of orchard garden, as well as an outside patio with table and chairs, with country views.

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A cozy living area features a wood burner set into a simple mantel, complemented by a glass coffee table with wooden legs. Two colorful armchairs, one yellow and one teal, are arranged around the space, with natural light streaming through the windows adorned with potted plants.