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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

4.87 out of 5 average rating, 326 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...

Rental unit in Weymouth

4.92 out of 5 average rating, 127 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, 131 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

Guesthouse in Dorchester

4.97 out of 5 average rating, 300 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

4.97 out of 5 average rating, 190 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!

Townhouse in Dorset

4.93 out of 5 average rating, 105 reviews

Sailor's Watch: A beautiful home by the sea...

A spacious Grade 2 Listed Dutch Style harbourside merchant house which has been split into two homes. You will be renting our home which spans across the first and second floors. It has been recently refurbished and has wonderful views of the harbour. There is a garden out the back with table and chairs. Close to the main town, beach and amenities of Weymouth. Dogs will be charged at £20 each per booking, please let me know if you are bringing your dog with you.

Cottage in Dorset

4.99 out of 5 average rating, 339 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!

Rental unit in Weymouth

4.91 out of 5 average rating, 639 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 .

Place to stay in Weymouth

4.95 out of 5 average rating, 239 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.

Rental unit in Weymouth

5 out of 5 average rating, 422 reviews

Apartment with panoramic sea views

We are situated 600 yards, through the nature reserve, from the beach and at the top of the hill with panoramic views over Weymouth bay, beach and nature reserve. 3 miles from the town With loads of parking available outside .You’ll love my place because of the location, the views. good for couples, solo adventurers, business travellers and small, well behaved dogs.

Cottage in Dorset

4.85 out of 5 average rating, 377 reviews

Character cottage close to beach

Spacious and beautiful house 5 min walk to Chesil Beach. Free superfast wi-fi, well equipped kitchen including dishwasher and a cosy log burner in living room. Scandi style décor. Netflix and smart TV. Right in heart of Fortuneswell, Portland with some shops, pubs and restaurants close by. 10-15 min drive from Weymouth. Great for couples.

Bungalow in Weymouth

4.97 out of 5 average rating, 152 reviews

LITTLE RETREAT. Rural village close to the sea

Stay in a very warm and cosy cottage and enjoy all that Dorset has to offer or just chill out and relax. A one bedroom cottage set in the owners beautiful walled garden with guest parking. In a village with easy access to Dorset's fabulous coast, countryside and main attractions. Two local pubs and cafe within easy walking.

Vacation rentals for every style

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Chalets

Adventure-ready homes with après-ski style

Popular amenities for Weymouth and Portland District family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Cabin in Forton

4.9 out of 5 average rating, 154 reviews

Woodpecker Lodge - Log Cabin with Private Hot Tub

Shepherd’s hut in Ilminster

5 out of 5 average rating, 217 reviews

Romantic Shepherds Hut & Wood-fired Hot Tub

Home in Somerset

4.92 out of 5 average rating, 227 reviews

Country House - Pool Jacuzzi Escape Room Karaoke

Barn in Long Sutton

4.85 out of 5 average rating, 289 reviews

Somerset Threshing Barn w/ Pool, Hot Tub & Sauna

Home in Hamworthy Poole

4.97 out of 5 average rating, 363 reviews

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

Cottage in Dinnington

4.95 out of 5 average rating, 476 reviews

The Cottage, Parsonage Farmhouse with hot tub

Hut in Dorset

4.94 out of 5 average rating, 83 reviews

Astronomer Shepherd's hut

Home in Wimborne St Giles

4.94 out of 5 average rating, 149 reviews

Charming Country Cottage

Family- and pet-friendly home rentals

Cottage in Combpyne

4.94 out of 5 average rating, 335 reviews

Lidyates Cottage near Lyme Regis

Rental unit in Lyme Regis

4.91 out of 5 average rating, 423 reviews

Blue Horizons seaside flat in town centre

Guest suite in Morcombelake

4.91 out of 5 average rating, 423 reviews

Modern studio, hillside garden with amazing views

Guest suite in Cattistock Dorchester

4.91 out of 5 average rating, 392 reviews

Willow Annexe

Guest suite in Duntish

4.9 out of 5 average rating, 445 reviews

Duntish Studio

Home in Dorset

4.92 out of 5 average rating, 500 reviews

Tranquil Townhouse with Parking,minutes from Beach

Home in Beaminster

4.91 out of 5 average rating, 124 reviews

Wantsley Cottage

Rental unit in Dorset

4.83 out of 5 average rating, 418 reviews

1 The Gables

Family-friendly home rentals with a pool

Chalet in Dorset

4.94 out of 5 average rating, 249 reviews

Breathtaking sea views from this light, cosy lodge

Home in Preston Road

4.84 out of 5 average rating, 111 reviews

Spacious Caravan near sea Weymouth Bay Haven

Home in LYME REGIS

5 out of 5 average rating, 22 reviews

Your Own Private Indoor Pool. Rural Seaside

Home in Bridport

4.91 out of 5 average rating, 46 reviews

Moorbath Farmhouse with Indoor Pool & Hot Tub

Home in Blandford Forum

4.98 out of 5 average rating, 50 reviews

Flint Cottage for two with indoor pool & sauna

Rental unit in Whitchurch Canonicorum

4.94 out of 5 average rating, 256 reviews

The Duck Wing, quirky dog friendly apartment

Cottage in Sherborne

4.91 out of 5 average rating, 414 reviews

Secret Rural Retreat

Shepherd’s hut in Dorset

4.89 out of 5 average rating, 173 reviews

Everdene shepherd's hut

Destinations to explore