Family-friendly holiday rentals in Weymouth and Portland District

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Top-rated family-friendly rentals in Weymouth and Portland District

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Superhost

Cottage in Dorset

4.87 out of 5 average rating, 340 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...

Top guest favourite

Barn in Whitchurch Canonicorum

5 out of 5 average rating, 148 reviews

The Barn @ Lower Park Farm, Nr Lyme Regis

A luxury barn conversion set in an area of outstanding natural beauty. This property blends comfort and space with seductive and classy interiors situated in a converted milking parlour. The area is renowned for great walks, cycling and horse riding through the picture-perfect countryside of Marshwood Vale. The nearest beach 3 miles away, with Lyme Regis just 6 miles away. This property offers the best of both worlds in terms of scenery and pretty seaside towns. Ideal for Coastal Path walkers.

Guest favourite

Chalet in Weymouth

4.96 out of 5 average rating, 203 reviews

Summer Lodge

The Summer Lodge boasts uninterrupted views of the Fleet Lagoon and world famous Chesil Beach from its elevated position on the South West Coast Path (Jurassic Coast). Located just one mile from the Isle of Portland, the home of the 2012 Olympic sailing events and a short drive from Weymouth town centre and harbour, our stunning holiday home is perfectly situated for anyone wanting a coastal escape. Our sea view lodge sleeps 6 people. There are 2 double bedrooms and a small double sofa bed.

Superhost

Townhouse in Dorset

4.87 out of 5 average rating, 142 reviews

Historic Seaman Chaplaincy, Seaview all rooms

The Gift House Portland is a historic Seaman's Chaplaincy, 3 storey late Georgian stone house. All 4 spacious bedrooms have sea view & perfect for sunset watching. Dog friendly (1dog only) Locate in island village, 5-8 mins walk to pebble beach, 17th century pub, restaurants, good coffee, good chippy & grocery shop. Jurassic coast walks, sculpture park, Portland stone quarry, cycling, swimming, rock climbing, sea fishing, diving, kayak, sailing, paddling, windsurf & more are around.

Top guest favourite

Guest house in Dorchester

4.97 out of 5 average rating, 317 reviews

Lovely, Quiet Studio Annex (with Netflix)

Self contained, self catering studio annex based in the county town of Dorchester. The annex is suitable for 2 adults (a z-bed can be supplied for 1 child under 12). The towns amenities are all within a short walking distance, including the new 'Brewery Square' development. Great base to explore Dorset's fabulous coast, countryside and walk in the footsteps of Thomas Hardy's Casterbridge. Motorbike friendly, high chair & travel cot available. Complimentary tea and coffee. Netflix TV.

Top guest favourite

Home in Wynford Eagle

4.94 out of 5 average rating, 217 reviews

Woodpeckers Rest - Alpacas-Gardens-Brook-Tennis

Nestled in an area of Outstanding Natural Beauty, Wynford Eagle is one of West Dorset's hidden gems. Woodpeckers Rest is a cosy studio retreat, a haven for peace and relaxation which opens out onto a large terrace with stunning views of the valley, 8 acres of grounds and gardens and beautiful alpacas. A great base to explore Dorset, situated just 15 minutes from the Jurassic coastline and all this incredible area has to offer. Please also see listing for airbnb.com/h/swallows-return

Top guest favourite

Home in Lyme Regis

4.99 out of 5 average rating, 245 reviews

Grand Cosy Stay by the Seaside in Lyme Regis

‘Waterside’ sits on the River Lym, originally built in the 1800’s, inspired by France in the busy port trading days of Lyme Regis. This well photographed house commands its place along this notable stretch of water. Completely and beautifully renovated in early 2021. Enjoy views from the middle and top floor overlooking the 17th century Gosling Bridge and the ‘Lynch’ where the waterway divides to service the town mill. 4-minute walk to the beach, artisan shops & high street.

Top guest favourite

Cottage in Bridport

5 out of 5 average rating, 212 reviews

Berry Farm Cottage

Berry Farm Cottage nestles in a private area of the grounds of Berry Farm, which dates back to the 16th century. It is located in the charming Conservation Village of Walditch, within walking distance of Bridport. The Cottage itself has 2 bedrooms and two bathrooms with an open-plan living space and is set away from the main house in its own private grounds, with 1,200sqm (0.3acres) of orchard garden, as well as an outside patio with table and chairs, with country views.

Top guest favourite

Cottage in Dorset

4.97 out of 5 average rating, 206 reviews

Character cottage with sea views and parking

200-year old 'Quarryman's Cottage' is just a short walk from Chesil Beach and the South West Coast Path and the perfect base for a family holiday in Dorset. It offers a private balcony with stunning sea views, off-road parking, three bedrooms, and open plan dining/living room with log burner. The local area is fantastic for windsurfing, sailing, kitesurfing, paddleboarding, climbing, walking, bird-watching, diving and fishing. We hope you enjoy it as much as we do!

Top guest favourite

Cottage in Dorset

4.98 out of 5 average rating, 354 reviews

The Condo (Indoor Pool available May- end Sept)

Self contained detached cottage in a tranquil location close to the famous 'Jurassic Coast' ; Durdle Door, Lulworth, Corfe Castle, Weymouth and Dorchester are all a short drive away. Further attractions close by are Monkey World, Bovington Tank Museum, and Sculpture by the lakes. There is a well stocked village shop and good village pub. Dorset has so much to offer, with beautiful coastline and breathtaking scenery. Relax in the pool at your leisure!

Top guest favourite

Place to stay in Weymouth

4.94 out of 5 average rating, 253 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.

Top guest favourite

Apartment in Dorset

4.95 out of 5 average rating, 328 reviews

Your hideaway on Weymouth harbourside!

Harbour Hideaway....light and airy basement apartment with own courtyard in fantastic harbourside location. Permit parking for 1 car and dogs welcome. Main sandy beach 5 mins away and town is just across the bridge. Friday changeovers preferred if weekly durations. Please note that there are two single beds in the bedroom and a drop down King Size bed in the lounge (not in a separate room) x