Vacation rentals in Weymouth and Portland District

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Weymouth and Portland District

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Cottage in Easton

4.93 out of 5 average rating, 177 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.

Guest favorite

Condo in Dorset

4.9 out of 5 average rating, 397 reviews

1 Bed Apartment Portland near Weymouth Dorset

The apartment is located in Portland near to a Portland Port and 5 miles to Weymouth 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 shower.There is a sofa bed suitable for young children. Parking is nearby but free parking is available in the street.

Guest favorite

Guesthouse in Dorset

4.95 out of 5 average rating, 172 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

Townhouse in Wyke Regis

4.94 out of 5 average rating, 133 reviews

The Wyke Square House in charming Weymouth

The Wyke Square House is a delightful and comfortable home-away-from-home spread over three floors. Located in the heart of charming Wyke Regis, you are moments away from the town centre and Weymouth's coves and renowned beaches. There are plenty of great pubs and restaurants nearby, as well as loads of attractions. Whether you are here to relax or for work, to hike along the Jurassic Coast, or to sail or windsurf at the National Academy - welcome to our piece of Jurassic Coast paradise!

Guest favorite

Cottage in Easton

4.92 out of 5 average rating, 192 reviews

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.

Guest favorite

Condo in Weymouth

4.91 out of 5 average rating, 380 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.

Guest favorite

Condo in Dorset

4.97 out of 5 average rating, 121 reviews

Newly built self contained Annex in Weymouth

A new purpose built self-contained annex, located in one of Weymouth's most prestigious and quiet locations. Situated a few minutes walk from a local beach and with just a 10 minute walk to Weymouth harbour. The property is thoughtfully furnished to provide a comfortable experience. A large Juliet balcony and plenty of windows ensure a light and airy ambience. Private gated off road parking with security cameras leads to a rear self contained outdoor patio area and the main entrance.

Guest favorite

Townhouse in Dorset

4.93 out of 5 average rating, 105 reviews

Sailor's Watch: A beautiful home by the sea...

A spacious Grade 2 Listed Dutch Style harbourside merchant house which has been split into two homes. You will be renting our home which spans across the first and second floors. It has been recently refurbished and has wonderful views of the harbour. There is a garden out the back with table and chairs. Close to the main town, beach and amenities of Weymouth. Dogs will be charged at £20 each per booking, please let me know if you are bringing your dog with you.

Guest favorite

Bungalow in Dorset

4.96 out of 5 average rating, 110 reviews

Islands Wrest (The Galleon Rm). Pet friendly.

Nautical galleon themed room with own entrance, kitchen & shower room this is 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. A 20 min bus ride to Weymouth for more seaside fun! Set centrally on the Jurassic coast. This is a real hidden gem.

Superhost

Condo in Dorset

4.81 out of 5 average rating, 123 reviews

Harbour Holiday let with picturesque views

"Old Quayside View Apartment 2" is a 2 Bedroom self contained open plan apartment with stunning views over the entire length of Weymouth's Old Harbourside. Fully refurbished throughout ready for the 2022 season, new fitted kitchen and bathroom, fresh and light decor makes this ideal family accommodation. Old Quayside view is centrally located on the old harbourside only a short stroll to Weymouths glorious sandy beach, local restaurants and amenities.

Guest favorite

Rental unit in Weymouth

4.89 out of 5 average rating, 396 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.

Guest favorite

Townhouse in Dorset

4.91 out of 5 average rating, 173 reviews

Townhouse, garden, hot tub, breakfast terrace.

Family friendly house with a covered sun terrace and hot tub. Stay in the heart of Weymouth’s old town in a quiet residential street a short stroll from the historic harbour. Within walking distance are restaurants, pubs and several beaches with safe bathing. With the South Coast Footpath only 200m away and lines provided for crabbing on the harbour side (essential children’s entertainment), there’s something for everyone in sunny Weymouth!