Chalet vacation rentals in Weymouth and Portland District

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Top-rated chalet rentals in Weymouth and Portland District

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Top guest favorite

The exterior of Wyvern Apartment features natural wooden cladding, complemented by a dark front door and multiple windows. A covered porch area includes a railing, providing an inviting entrance. The surrounding greenery adds a touch of nature to the setting.

Chalet in Somerset

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.

Top guest favorite

A nearly-new static caravan is presented with a spacious wraparound sundeck, enclosed by a white railing. The exterior features large windows that allow natural light, while a paved path leads to the parking area for two cars beside well-maintained grass.

Chalet in West Lulworth

4.95 out of 5 average rating, 307 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.

Guest favorite

A wooden deck features a neutral-toned table surrounded by matching chairs, providing a seating area with panoramic views of Swanage Bay. The coastline can be seen in the distance, framed by lush greenery and a clear blue sky.

Chalet in Dorset

4.94 out of 5 average rating, 278 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!

Top guest favorite

The living area features a red couch, wooden chairs, and a small dining table. A television sits on a stand, and sunlight fills the space through large windows adorned with light curtains. A bookshelf provides additional storage and decor against the wall.

Chalet in East Stoke

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).

Guest favorite

A sandy beach stretches across the foreground, with large stones placed sporadically. In the distance, a row of white chalets is visible against a backdrop of rolling hills under a cloudy sky.

Chalet in Puncknowle

4.95 out of 5 average rating, 102 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

Top guest favorite

The spacious mezzanine bedroom features a king-size bed with crisp cotton bedding and plush decorative pillows. A wooden bench draped with a soft throw sits at the foot of the bed. Nautical-inspired porthole windows and angled skylights allow natural light to enhance the serene decor.

Chalet in Uplyme

5 out of 5 average rating, 8 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

A charming shepherd's hut displays a rustic wooden exterior under a clear blue sky. A deck area is featured, accompanied by two green chairs for outdoor seating. The surrounding landscape includes open grassy space and trees, creating a serene atmosphere.

Chalet in Salwayash

4.8 out of 5 average rating, 5 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.

Guest favorite

The open-plan living area features modern furnishings, including a comfortable seating arrangement and a stylish kitchen with a view of the Fleet Lagoon. Natural light floods the space through large glass doors, leading to a south-facing veranda adorned with outdoor seating.

Chalet in Weymouth

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

The exterior of The Duck House is depicted, showcasing a charming two-story chalet surrounded by lush greenery. The light yellow walls complement the natural landscape, while windows reflect the tranquil sky. The well-maintained lawn offers open space for relaxation and play.

Chalet in Whitchurch Canonicorum

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.

Guest favorite

The chalet-style house features a charming red-brick exterior with a gabled roof. Large windows allow natural light into the living spaces. A well-maintained front garden complements the front entrance, while a blue garage door adds a touch of color to the facade.

Chalet in Dorset

4.96 out of 5 average rating, 24 reviews

Lovely seaside home just 2 minutes from the beach

Perfect for family holidays and weekends away with friends, The Dolphins is a spacious chalet-style seaside house just 2 minutes from Swanage's sandy beach and an easy stroll into the centre of Swanage town. It is a self catering property set over 2 floors, suitable for up to 8 guests with 4 bedrooms, 2 bathrooms, a large lounge, dining room, kitchen, and spacious garden with a substantial patio giving plenty of room for fun and games and alfresco dining.

Top guest favorite

A spacious living area showcases comfortable seating with a light blue sofa and a wooden coffee table. Large glass doors open to a balcony with sea views, while curtains frame the windows. Dining arrangements are visible with a table set for several, enhancing the welcoming ambiance.

Chalet in Ringstead

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.

Top guest favorite

A row of modern wooden chalets stands along the stony beach, facing the shoreline. Driftwood and smooth stones are arranged in the foreground, providing an natural contrast to the structured design of the chalets. The entryways are framed by wooden decks, emphasizing the coastal location.

Chalet in Dorset

4.96 out of 5 average rating, 130 reviews

Chalet 31 Monmouth Beach Lyme Regis

A delightful, modern, petite wooden chalet located on Monmouth beach in Lyme Regis, overlooking the Jurassic coastline, famous Cobb and fossiling areas including the ammonite graveyard. A unique design, 10/15 minutes walking distance of the main town, shops, bars and restaurants. Perfect location for a relaxing break watersports enthusiasts, fossil hunting, walkers or artists. No pets allowed.