Vacation rentals in Weymouth and Portland District

4.97 out of 5 average rating, 36 reviews

Chalet in Dorset

Our Plaice by the Sea

'Our Plaice by the Sea' is a 2 bedroom caravan, on the flagship Littlesea Haven holiday park. Our Plaice feels like a home from home, reminding us of a beach hut with its pale- blue cladding, decking out front and stunning views of Chesil Beach; it stands out, giving a relaxed seaside vibe. There’s plenty to do on-site with an indoor and outdoor pool, adventure golf, arcade, day and night entertainment (Haven passes to be purchased) fabulous coastal path walks and near to the Jurassic coastline.

4.93 out of 5 average rating, 91 reviews

BEACH HOUSE: sleeps 14 right on Sea / Beach / Sand

- Stunning sea and beach views: >80 reviews! - Right on beach without crossing any road - safe for children - Large 1840s period house, superbly equipped, quirky charm - Quieter end of town, exclusive use + 2 car permits - Space for several families to spread out, great privacy - Beach for a mile in both directions - Recent upgrades, was guesthouse - "Weymouth Best Beach in UK" (2023 Sunday Times) - UK's 3rd sunniest place - Harbour boat trips, sailing - Jurassic coast, unspoilt countryside

4.96 out of 5 average rating, 70 reviews

Condo in Canford Cliffs

Beach Retreat 1 - 400m to beach-Luxury 2 bed Flat

Luxury, family friendly apartment in an outstanding location with everything on your doorstep! On a quiet street in exclusive Canford Cliffs village, moments from top restaurants, bakery/deli, 2 gastropubs and Tesco. 5 min scenic woodland walk to stunning award winning Sandbanks beach and children's Pirate playground. Ideal luxury family holiday with the perfect location to park the car and enjoy the beach, watersports and entire holiday on foot. Free parking provided & no Airbnb cleaning fees!

4.96 out of 5 average rating, 53 reviews

Tent in Corfe Castle

Farm glamping close to Swanage coast (2 of 5)

Glamping in one of our 5 rustic and very comfortable safari tents on our working dairy farm close to Swanage. Tents sleep up to 4 guests in a king bed, twin beds or double cabin style bed. Beds made up. Bring your own towels. Own shower room. Cook on the wood burning stove (with oven) or BBQ outside. Basic electricity providing overhead lanterns and a couple of sockets for charging mobiles. Firewood included. Dog welcome at an extra £25 (must be booked in and paid for prior to arrival)

4.88 out of 5 average rating, 172 reviews

Cottage close to beaches and restaurants

A beautiful two bed house with garden and off street parking in an excellent location in Poole Dorset. The property features a new luxury bathroom installed in June 2021. There is an additional double sofa bed in the second living room. The property is moments from popular Ashley Cross with its bustling bars and restaurants and only a five minute drive to the award winning beaches of Sandbanks and Branksome Chine. Guests also have the open spaces of Poole Park only 5 minutes walk away.

Superhost

4.98 out of 5 average rating, 40 reviews

Idyllic Harbour House

A gem of a beautiful Grade II listed harbour house, situated in the most desirable area of Weymouth's harbour. Great for families & friends who want to make special memories. A spacious 5 bedroom (3 en-suite), recently renovated in a stylish contemporary finish. Everything you will need is in walking distance.... restaurants, bars, shops, beach and boat trips. Situated on the quiet side of the harbour, a lovely peaceful location with a private garden, ideal for BBQs in the summer.

Superhost

Cottage in Bridport

4.9 out of 5 average rating, 122 reviews

5* Cottage on Chesil Beach Dorset Jurassic Coast

SHORT HOUSE, CHESIL BEACH; beautiful 'Switch off the world', 5* Seaside Cottage on Dorset's World Heritage Jurassic Coast. Private access to Chesil Beach; 400m. Dogs welcome. Spectacular ocean views, dining terrace, large living space, fully equipped kitchen, 2 double ensuite bedrooms, king size (or twin) beds, Egyptian linen, fluffy towels & sandpit in a lovely garden. 43" Sony UHD TV + SKY Q, DVD & Bose Sound. A peaceful place to isolate, recuperate & build sandcastles.

Superhost

Cottage in Blandford Forum

4.84 out of 5 average rating, 324 reviews

Ranmoor Estate - Kestrel Lodge - Hot Tub & A/C

Experience the charm of a unique, pet-friendly glamping lodge featuring two cozy bedrooms. Enjoy the luxury of private hot tubs and a barbecue on your patio, perfect for relaxing evenings under the stars. This fully air-conditioned retreat comes equipped with a modern kitchen, complete with a fridge, ensuring you have everything you need for a comfortable stay. Each room is fitted with smart TVs, providing entertainment at your fingertips for a delightful getaway.

4.96 out of 5 average rating, 111 reviews

Hut in Dorset

Secret cabin by stream in lovely wild garden

Enjoy a magical stay in our secret cabin, situated in our award-winning wild garden beside a lovely stream. This storybook cabin is nestled in nature but is also in the heart of the pretty small town of Beaminster. It offers the best of both worlds when it comes to glamping! Venture out to pubs and restaurants in easy walking distance and return to the sound of an owl hooting. The perfect base for exploring the countryside and coastline of beautiful West Dorset.

4.95 out of 5 average rating, 39 reviews

Beachside Cottage with Panoramic views of the sea

New to Airbnb for 2022 - under our ownership Beachside Cottage was the GOLD WINNER Best for Beaches 2019 Sykes Gems award that recognises the very best properties in the collection. The upstairs balcony has panoramic views of the sea and it is literally a 20 second stroll to the beach. Excellent water sports can be enjoyed directly from the front of the property, or perhaps you would prefer to observe, with excellent views from the balcony or living room.

4.98 out of 5 average rating, 118 reviews

Home in Tisbury

Spacious 4-bedroom holiday home in Tisbury

Beech House is a new, stone-built 4-bedroom house with a large open-plan living area and beautiful views over rooftops to the countryside beyond. Nestled in the heart of the popular small town of Tisbury, it’s a convenient stroll away from high-street shops, pubs and the train station. Despite its central location, the house is tucked away just off a quiet lane, making it wonderfully peaceful and homely.