Vacation rentals in Weymouth and Portland District

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Top-rated vacation rentals in Weymouth and Portland District

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Guest favorite

Cottage in Dorset

4.88 out of 5 average rating, 355 reviews

18th Century Coastal Cottage

This historic home features original stone floors, rustic wood beam ceilings, a wood-burning fireplace, modern finishes, a sauna, and a private back patio overlooking the beach. Breathe in the refreshing ocean air from this hillside retreat. I’m sorry I have a no pets policy at the cottage. This cottage has steep stairs, low ceilings, a very low rise bed and a low sofa as seen in the pictures. 60 Mallams was built in approximately 1760 and still has many rustic features throughout. The cottage has two levels, ground floor consists of open plan lounge leading to the kitchen then conservatory with shower room. Which opens out into courtyard garden with a terrace and sea views. 1st floor has the main bedroom with a super king size bed and separate bathroom with a free standing bath with room for two.. Private parking on driveway 24hr key access safe by the front door I can be contacted at any time throughout your stay. The property is located just a five minute walk from Chesil Beach. It is also close to a number of the town's local shops and cosy pubs. There’s plenty of coastal walks all around Portland The sailing club is close offering various water sports There is bus services to and from Weymouth. There are amazing coastal walks around Portland. Please be mindful of the rubbish I have food waste bins , glass only tubs and the larger of the wheelie bins (green) are recycling only ( cans paper and plastic) and the black bins are general rubbish.. please be careful with the rubbish because if it's all mixed up the bin men won't take it away...

Guest favorite

Cottage in Easton

4.93 out of 5 average rating, 205 reviews

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 bbq, bistro table and chairs A perfect holiday location all year round, for either sun and relaxation, or activities windsurfing, sailing, diving, rock climbing, fishing or just walking and bird watching.

Top guest favorite

Condo in Dorset

4.91 out of 5 average rating, 485 reviews

1 Bed home near Sailing academy Portland, Weymouth

The home is located in Portland near to a Port and 5 miles to Weymouth also 10 min walk to sailing academy The area is noted for diving,windsurfing,fishing,sailing,extensive coastal walks,rock climming, cycle routes It is a one bedroom apartment.There is a small Beach and it’s a short walk to shops,cafe's and restaurants.Includes an open plan kitchen,living room and en-suite bathroom with electric showerThere is a sofa bed on request Parking is nearby but free parking is available in the street

Top guest favorite

Bungalow in Dorset

4.95 out of 5 average rating, 179 reviews

Islands Wrest (The Galleon Rm). Pet friendly.

Nautical galleon themed room with own entrance, kitchen & shower room this your own space within owner occupied property. Explore Portland, an Island that features breathtaking views, beautiful walks. Castles, 3 lighthouses. Chesil beach. a Museum, rock climbing, wildlife, water sports. History of smugglers & pirates explore Church Ope Cove. 20 min on bus to Weymouth for more seaside fun! Set centrally on the Jurassic coast. This is a real hidden gem. Not suitable for infants (Adults only)

Guest favorite

Guesthouse in Dorset

4.95 out of 5 average rating, 253 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.

Guest favorite

Condo in Weymouth

4.92 out of 5 average rating, 448 reviews

Stunning Beachfront apartment overlooking the sea

A brand new apartment just 50 steps from the beach with free parking in the heart of Weymouth directly on the Esplanade with panoramic sea views of the award winning beach. Well equipped and nestled amongst shops and restaurants . Just minutes walk to bars , the harbour and train station. Fully fitted kitchen with family size fridge freezer, oven, microwave, toaster, kettle, cutlery, crockery, dishwasher, washing machine, flat screen TV's, Wifi, Hand, bath and beach towels provided.

Top guest favorite

Condo in Dorset

4.91 out of 5 average rating, 117 reviews

Beachside View

Enjoy easy access both beach and town centre from this beachfront couples' retreat. This top floor (3rd floor) flat has panoramic views across the bay and there's even a telescope. This apartment is right next to a M&S food hall and within 100m of a fish n chip shop, a Chinese takeaway, a traditional pub and several bars and restaurants. There is a king size bed in the bedroom and a sofa that pulls out into a bed in the lounge. Access to the bathroom is through the bedroom.

Guest favorite

Guesthouse in Southhill

4.84 out of 5 average rating, 277 reviews

Bright & Snug annexe with Parking in Weymouth

Welcome to our one bedroom self contained private accommodation with parking space in Weymouth. Consisting of a double bed, two seater sofa, mini kitchen unit with sink, kettle & toaster, fridge, smart TV, chest of drawers, shower room. Weymouth town Centre, train station and Weymouth’s popular beach is a 20 minute walk through the RSPB nature reserve, where you will see swans, ducks & plenty of bird species. Pub, pharmacy & shop is only a 5 min stroll down the road.

Guest favorite

Apartment in Weymouth

4.9 out of 5 average rating, 436 reviews

Flat One The Beaches

***Flat one the Beaches is in a central position & can be noisy in the evenings especially at the weekends***Recently converted Grade II listed building on Weymouth seafront. The apartment is one of four located off a private inner courtyard on the first floor. well equipped apartment across the road from Weymouth’s award winning beach and nestled a stones throw away from Weymouth town with its great choice of harbour side restaurants and bars.

Top guest favorite

Place to stay in Dorset

4.96 out of 5 average rating, 259 reviews

The Hide in the treetops near weymouth town/beach

Open plan space: sleeps 2; king size bed; bed linen. Kitchen with induction hob; electric oven; microwave and fridge freezer; coffee machine; tea towels. Ensuite shower room; hand towels & Bath sheets. Beach Towels not provided so please remember to pack yours! Comfy sofa; dining table and 4 chairs. Large TV and wifi. No children of any age and no animals/pets allowed. Smoking strictly prohibited inside The Hide or on the grounds.

Top guest favorite

Tiny home in Weymouth

4.89 out of 5 average rating, 227 reviews

Cosy Sail Loft on the harbour.

This special place is close to everything, making it easy to plan your visit. With your own parking space, own entrance, bedroom / lounge, own kitchen and Bathroom, you can be fully self sufficient or enjoy all the local pubs and restaurants on your door step. Literally right on the harbour front and only a minute away from the beach, this cosy property allows you to enjoy all of this seaside town within a few minutes.

Guest favorite

Place to stay in Weymouth

4.94 out of 5 average rating, 268 reviews

Pebble Lodge

Pebble Lodge is a stylish, modern and luxury home from home for four guests (plus one infant). Situated on the five star Chesil Beach Holiday Park, Pebble Lodge boasts an uninterrupted view of the Fleet Lagoon and Chesil Beach, infamous parts of the Jurassic Coast. Beautiful accommodation, finished with some personal touches really makes Pebble Lodge the perfect coastal escape in all seasons.