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Family-friendly vacation rentals in Weymouth and Portland District

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

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Cottage in Dorset

4.88 out of 5 average rating, 309 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...

Apartment in Weymouth

4.92 out of 5 average rating, 117 reviews

Marina Place Weymouth

Marina Place Weymouth Is a modern very good sized 2 bedroom 2nd floor Apartment with wonderful views over inner harbour, & marina, Swannery & bowls green. It’s on the edge of town & a 2 minute walk to the beach & shops Its 5 minutes from Train & Bus Station. It has lift, gated, parking for one vehicle. It has Juliet balconies from the bedrooms & kitchen dinner with great views & large bathroom & also ensuite shower room on main bedroom which makes it idea for families or couples. SORRY NO PETS

Home in Dorset

4.94 out of 5 average rating, 120 reviews

Blue Bay Cottage - Cove Street, Weymouth Harbour

Beautiful 3 bedroom cottage close to Weymouth harbour and town centre. Own entrance leading to dining room, kitchen, conservatory, cloakroom and rear courtyard. Stairs to lounge with gas stove, bathroom with large shower and single bedroom. Further stairs to master bedroom and twin bedroom. Kitchen with integrated dishwasher, fridge, Neff hide and slide oven, microwave. The cottage has gas central heating and a parking permit for on street/harbourside parking. WiFi and outside space to sit

Cottage in Portesham

4.78 out of 5 average rating, 360 reviews

Pond outside your bedroom window.

Self-contained bedroom, a sitting room and shower room. Your suite of rooms is separate from the house with its own entrance. The windows overlook the village duck pond and spring and pretty waterfall. There is parking, for your car, at your door. We're in a Dorset village with Trafalgar history, centuries old church, busy pub. The coast is only a couple of miles away. We are on the Dorset Coastal Path and the SSSI Jurasic Coast. £7.50 for a full Dorset breakfast. Evening meal £7 to £12.

Cottage in Winfrith Newburgh

4.98 out of 5 average rating, 252 reviews

Bramble - 17th Century Barn Conv -enclosed garden

Bramble Barn is a beautiful 17th-century barn conversion situated down a private road just 4 miles from Lulworth Cove, Durdle Door and the Jurrasic Coast World Heritage Site. This large splendid brick barn has been converted into two identical properties creating accommodation of the highest standards. Each barn has its own enclosed garden and a south-facing terrace, ideal for eating out. Tadnoll Heath, a Dorset Wildlife Trust Reserve, lies just to the north. Ample off-road parking.

Guesthouse in Dorchester

4.97 out of 5 average rating, 276 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.

Cottage in Dorset

4.98 out of 5 average rating, 162 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!

Cottage in Dorset

4.98 out of 5 average rating, 314 reviews

The Condo (Indoor Pool available May-Oct only)

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!

Apartment in Weymouth

4.91 out of 5 average rating, 602 reviews

Splendid Quiet Ground Floor Apartment Near the Sea

This gorgeous large studio apartment with separate entrance is contained within an historic Georgian house, minutes from the ocean. Peace and quiet are ensured by a large well tended front garden with off street parking. The accommodation has a spacious shared patio, giving way to an established secluded garden. The apartment boasts a stylish fully fitted kitchen and leather Chesterfield sofa, chairs and a large comfy bed .

Chalet in Weymouth

4.95 out of 5 average rating, 170 reviews

Summer Lodge

The Summer Lodge boasts uninterrupted and unrivaled views of the Fleet Lagoon and world famous Chesil Beach from its elevated position on the Jurassic Coast path. 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.

Place to stay in Weymouth

4.94 out of 5 average rating, 208 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.

Condo in Dorset

4.95 out of 5 average rating, 275 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

Vacation rentals for every style

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Popular amenities for Weymouth and Portland District family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Cottage in Dinnington

4.95 out of 5 average rating, 430 reviews

The Cottage, Parsonage Farmhouse with hot tub

Cottage in Dorchester

4.99 out of 5 average rating, 167 reviews

Charming Brick Cottage with a Patio and Hot Tub

Home in Poole

4.97 out of 5 average rating, 334 reviews

Poole Harbour View,Top Location Opp Hot-tub /Sauna

Home in Somerset

4.91 out of 5 average rating, 208 reviews

Country House - Jacuzzi Pool Escape Room Karaoke

Shepherd’s hut in Ilminster

5.0 out of 5 average rating, 202 reviews

Romantic Shepherds Hut & Wood-fired Hot Tub

Cabin in Forton

4.89 out of 5 average rating, 149 reviews

Woodpecker Lodge - Log Cabin with Private Hot Tub

Cottage in Dorchester

4.74 out of 5 average rating, 61 reviews

Nutley Farm Gatehouse

Home in Weymouth

4.67 out of 5 average rating, 209 reviews

Large house close to sea with HOT TUB sleeps 12

Family- and pet-friendly home rentals

Home in Easton

4.94 out of 5 average rating, 131 reviews

Top To Bottom beautiful cottage heart of Easton

Guest suite in Cattistock Dorchester

4.9 out of 5 average rating, 369 reviews

Willow Annexe

Apartment in Dorset

4.82 out of 5 average rating, 383 reviews

1 The Gables

Guest suite in Duntish

4.91 out of 5 average rating, 405 reviews

Duntish Studio

Tiny home in Dorset

4.9 out of 5 average rating, 212 reviews

North End Farm, Old Cricket Pavilion

Bungalow in Dorset

4.95 out of 5 average rating, 151 reviews

Dairy House Self Catering Annexe

Bus in Owermoigne

4.85 out of 5 average rating, 224 reviews

Magic Bus RV nr coastal Durdle door play garden

Cottage in Hooke

4.93 out of 5 average rating, 225 reviews

The Little House, Hooke, Nr Bridport, West Dorset

Family-friendly home rentals with a pool

Chalet in Weymouth

4.93 out of 5 average rating, 121 reviews

Bowleaze Cove with a view

Home in Preston Road

4.83 out of 5 average rating, 109 reviews

Haven Weymouth Bay Holiday Park

Apartment in Whitchurch Canonicorum

4.94 out of 5 average rating, 235 reviews

The Duck Wing, quirky dog friendly apartment

Chalet in Dorset

4.94 out of 5 average rating, 230 reviews

Breathtaking sea views from this light, cosy lodge

Cottage in Sherborne

4.91 out of 5 average rating, 395 reviews

Secret Rural Retreat

Home in Blandford Forum

4.98 out of 5 average rating, 44 reviews

Cottage for two with indoor swimming pool & sauna

Home in LYME REGIS

5.0 out of 5 average rating, 19 reviews

Your Own Private Indoor Pool. Rural Seaside

Home in Devon

4.81 out of 5 average rating, 16 reviews

Family Farmhouse with pool, sleeps 15

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