Chalet holiday rentals in Weymouth and Portland District

4.93 out of 5 average rating, 120 reviews

Wyvern Apartment - Where your comfort matters

Wyvern Apartment is a newly converted studio apartment which is close to beautiful countryside and many great attractions. We have designed the apartment with our guests' comfort in mind and it has been ideally equipped for both business and pleasure guests. There is free parking, a flat screen smart TV, free unlimited WI-FI along with lots of other little touches to help make your stay as welcoming and convenient as possible. The apartment boasts a well equipped kitchen and walk-in shower room.

4.95 out of 5 average rating, 306 reviews

Durdle Door & Lulworth Cove. Family/Dog friendly.

Our holiday home is located in Durdle Door Holiday Park near the famous stone arch of Durdle Door, a UNESCO World Heritage site. It's in a great position, being one of the closest homes to the beach access path, and boasts sea glimpses from the sun deck and living room window. Featuring all mod-cons it is a really comfortable home-from-home. The park is quiet and well-maintained with a shop, restaurant, bar and play-park. Lulworth Cove, along with its pubs and restaurants are a short walk away.

4.94 out of 5 average rating, 277 reviews

Breathtaking sea views from this light, cosy lodge

Seascape is a bright, airy lodge down its own drive at the edge of Swanage Bay View. Adjoining Townsend Nature Reserve it enjoys utter tranquillity and spectacular views over the bay, as seen on 'A Place in the Sun'. With its tasteful modern furnishings, central heating and double glazing, Seascape is a cosy winter retreat, while in Spring and Summer use of a 1903 beach hut on a private beach is included. In addition, guests enjoy the amenities of SBV - all within a 15 min walk of the seafront!

Superhost

4.79 out of 5 average rating, 42 reviews

Peaceful retreat ~ Everdene Jurassic Coast

Everdene, a beautiful warm & contemporary 3 bedroom holiday cottage located in Upwey village near to Weymouth Beach, ideally located for families & friends to holiday & explore Dorset. Spacious Everdene has a master king size bedroom upstairs with a large luxury ensuite bathroom, 2 further bedrooms downstairs with flexible twin or double set up for your group & a second family bathroom. Everdene has beautiful views over the meadows with a private garden too. More dates available on request

4.96 out of 5 average rating, 145 reviews

Chalet ‘Little Coppice’ East Stoke Wareham Dorset

A lovely self contained two bedroomed cottage with its own private garden in a rural location on the site of an equine residence. Easy access to woodland walking, and 1.5 miles from nearest village with pub, shops and mainline railway station. Nearby attractions include Monkey World, Bovington Tank Museum, Swanage Steam Railway, Weymouth Beach, Corfe Castle (with inflatable water park), Studland Beach (fantastic National Trust sandy beach), Lulworth Cove and Lulworth Castle (for Bestival).

4.95 out of 5 average rating, 101 reviews

Little Beach House on West Dorset’s Jurassic coast

Little Beach House is located in the unspoilt hamlet of West Bexington only 20 yards from Chesil beach which is on the Jurassic coast of West Dorset. It has uninterrupted views of the sea from the lounge and bedroom and has a very sunny aspect being a south-facing garden, outside it has a grassed back and front garden with private parking West Bexington has a hotel with restaurant and bar, it also has great food at the Club house restaurant, all within a short walking distance of the Chalet

5 out of 5 average rating, 7 reviews

Luxury Riverlodge & Sauna by Lyme Regis

An idyllic, luxury stay & sauna. Immerse yourself in serenity at this chalet inspired lodge, built purely for rest & relaxation. This spacious stay is architecturally curated to inspire comfort and tranquillity. Gaze up at the high pitched ceilings and stunning glass fronted mezzanine floor. With unobstructed view of the glass fronted wood-burner, perfect for cosy evenings and peaceful mornings. Stroll the River nature trail effortlessly connecting you to the vibrant heart of Lyme Regis.

Superhost

5 out of 5 average rating, 4 reviews

Tranquil, Luxury Shepherd’s Hut, Hot Tub & Views

Welcome to Primrose, our hand-crafted oak shepherd's hut, thoughtfully designed to offer a peaceful and luxurious countryside retreat. Nestled in the grounds of Sea View Farm and bordered by open farmland, Primrose boasts uninterrupted panoramic views stretching across the rolling hills all the way to the sea at West Bay. Whether you’re looking to explore the coast, enjoy romantic downtime, or simply escape from it all, Primrose offers the perfect balance of rustic charm and modern comfort.

4.97 out of 5 average rating, 254 reviews

The Fleet Retreat

Our luxurious accommodation, ‘The Fleet Retreat’ boasts views of the Fleet Lagoon, a stunning nature reserve nestled between world famous Chesil beach and the South West Coast Path. It is situated just 1 mile from Portland and 2 miles from Weymouth town centre Our luxurious accommodation is in close proximity to an abundance of beaches, walks and activities. It is perfect for couples wanting to while away a lazy weekend or for families wanting to explore all that Dorset has to offer.

Superhost

4.88 out of 5 average rating, 220 reviews

The Duck House. A child/dog friendly rural chalet

The Duck House is a lovely child/dog friendly chalet nestling in the orchard at Plenty Cottage. Quiet and peaceful it's the perfect retreat for a family - and dogs are especially welcome! Open plan living it’s a comfortable and home from home. A wonderful rambling garden, summerhouse, BBQ and a (free) heated swimming pool (1st April - 31st Sept). The mantra is 'No Stress'. Ample parking, dog/child friendly pub 7 mins walk away. Wonderful NT beaches just five min drive.

5 out of 5 average rating, 18 reviews

Kingfisher - Creek Caravan Park Ringstead

Welcome to Kingfisher, a spacious lodge at Ringstead Bay that offers the perfect blend of comfort and seaside charm. With plenty of room to relax, this lodge is ideal for long stays by the beach. Take in the stunning sea views from the balcony, explore nearby coastal trails, or visit local spots like Weymouth and Durdle Door. Our friendly staff is on hand to ensure a memorable and relaxing stay.