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Vacation rentals in Weymouth and Portland District

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Top-rated vacation rentals in Weymouth and Portland District

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Cottage in Dorset

4.88 out of 5 average rating, 307 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...

Feb 12 – 19

G$45,872 GYD per night

Guest suite in Weymouth

4.96 out of 5 average rating, 350 reviews

Charlottesview - On The Beach with Parking inc.

Situated overlooking Weymouth Bay and the South West Coast Path with direct beach access through the car park and garden. Ground floor apartment access through secure communal grand entrance, via six stone steps. Georgian property (1776) with varied history through Georgian/Victorian era and two world wars, spacious, high ceilings, chandeliers and many period features. Covered semi underground car parking space in adjoining building with no roads to cross to access Charlottesview or the beach.

Sep 24 – Oct 1

G$32,391 GYD per night

Condo in Dorset

4.9 out of 5 average rating, 314 reviews

1 Bed Apartment Weymouth and Portland, Dorset

The apartment is located in Portland 5 miles to Weymouth The area is noted for diving,windsurfing,fishing,sailing,extensive coastal walks and cycle routes to Weymouth. It is a one bedroom apartment.There is a small Beach 30 seconds of the doorstep and it’s a short walk to shops,cafe's and restaurants.Includes an open plan kitchen,living room and en-suite bathroom with electric shower.There is a sofa bed suitable for young children. Parking is nearby but free parking is available in the street.

Nov 17 – 24

G$17,255 GYD per night

Guesthouse in Dorset

4.96 out of 5 average rating, 109 reviews

Seaside studio cabin minutes from 'secret' beach

Tucked away up an unmade track & five minutes walk from a 'secret' local beach; Cove Cabin is a compact, stylish, private space; perfect for a couple or two companions. On the doorstep of lesser known beaches & gardens but not far from Weymouth's bustling scenic harbour & golden sands. Ideal stop off whilst walking the SW Coast Path. The perfect area for watersports, wild swimming, walking, mooching around the harbour & locality, sampling the local seafood & eateries & just simply relaxing.

Jun 21 – 28

G$22,621 GYD per night

Cottage in Portland

4.89 out of 5 average rating, 129 reviews

Number 107, Isle of Portland, Dorset

Number '107' positioned on the Isle of Portland with its close proximity to Chesil Beach is a spacious, comfy & well equipped cottage within 5 mins walk of the beach. Situated close to all local amenities with shops, cafes & pubs all within a short walking distance. The cottage is perfect for families & couples looking for a cosy seaside retreat & those looking for a place to relax after a day of walking, climbing, and water sports. An ideal base for exploring Jurassic Coast and beyond.

May 9 – 16

G$24,756 GYD per night

Cottage in Easton

4.92 out of 5 average rating, 165 reviews

Milly Moll Cottage, next to Church Ope Cove.

Julie and Matt welcome you to Milly Moll Cottage. A quirky C18th, grade 2 listed property full of character and charm, just next door to the Portland museum. Built of Portland stone with original fireplaces and a cozy lounge with a log burner, from here you can explore the Jurassic coast. It’s a 2 minute walk to Church Ope Cove, either passing under Rufus Castle arch or via the ruins of St Andrews church and is ideally placed for numerous outdoor pursuits. We hope you will enjoy your stay.

Jun 3 – 10

G$25,185 GYD per night

Condo in Weymouth

4.91 out of 5 average rating, 331 reviews

Cosy beach front apartment overlooking the sea

A brand new apartment just 50 steps from the beach with free parking in the heart of Weymouth directly on the Esplanade with panoramic sea views of the award winning beach. Well equipped and nestled amongst shops and restaurants . Just minutes walk to bars , the harbour and train station. Fully fitted kitchen with family size fridge freezer, oven, microwave, toaster, kettle, cutlery, crockery, dishwasher, washing machine, flat screen TV's, Wifi, Hand, bath and beach towels provided.

Oct 3 – 10

G$32,887 GYD per night

Bungalow in Weymouth

4.98 out of 5 average rating, 240 reviews

Sunnyside Lodge

Sunnyside Lodge is a fully self-contained property with a private entrance and off-road parking located 1.4 miles from Weymouth town centre. The property has been converted to a holiday let, decorated to a crisp, clean and comfortable finish. The property comes with access to high speed WiFi, Sky Q and is fully fitted with fire alarms and a CO2 alarm. The location provides excellent transport links to surrounding local attractions including The Jurassic Coast - a World Heritage Site.

Feb 13 – 20

G$26,546 GYD per night

Cottage in Dorset

4.92 out of 5 average rating, 134 reviews

Chesil Cove Holiday Cottage

A Grade II listed traditional characterful fisherman's cottage located adjacent to the iconic Chesil Cove on the island of Portland, part of the Jurassic Coast. The cottage is small and cosy with two bedrooms, small upstairs wetroom and modernised kitchen with solid wood breakfast bar. The wooden stairs are very steep and narrow so the property is not suitable for young children. An enclosed south-facing backyard is a suntrap for private sunbathing, drying swimming/diving gear etc.

Jun 19 – 26

G$23,785 GYD per night

Apartment in Chickerell

4.95 out of 5 average rating, 140 reviews

Little Knapp

In a designated area of outstanding natural beauty “Little Knapp” a modern coach house style self contained studio apartment is nestled within a private hamlet very close to all the amenities of Chickerell and within a five minute drive of the coastal resort of Weymouth. Situated on the famous Jurassic coast road and only a five minute walk to join the Jurassic South Coast foot path, “Little Knapp” is ideally placed for exploring the wonderful county of Dorset.

Apr 25 – May 2

G$21,654 GYD per night

Place to stay in Dorset

4.96 out of 5 average rating, 168 reviews

The Hide in the treetops near weymouth town/beach

Open plan space: sleeps 2; king size bed; bed linen. Kitchen with induction hob; electric oven; microwave and fridge freezer; coffee machine; tea towels. Ensuite shower room; hand towels & Bath sheets. Beach Towels not provided so please remember to pack yours! Comfy sofa; dining table and 4 chairs. Large TV and wifi. No children of any age and no animals/pets allowed. Smoking strictly prohibited inside The Hide or on the grounds.

Jun 12 – 19

G$30,089 GYD per night

Tiny home in Weymouth

4.85 out of 5 average rating, 140 reviews

Cosy Sail Loft on the harbour.

This special place is close to everything, making it easy to plan your visit. With your own parking space, own entrance, bedroom / lounge, own kitchen and Bathroom, you can be fully self sufficient or enjoy all the local pubs and restaurants on your door stop. Literally right on the harbour front and only a minute away from the beach, this cosy property allows you to enjoy all of this seaside town within a few minutes.

Jan 15 – 22

G$16,932 GYD per night

Vacation rentals for every style

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Houses

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Chalets

Adventure-ready homes with après-ski style

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Weymouth and Portland District vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Weymouth and Portland District

Cottage in Fortuneswell

4.98 out of 5 average rating, 184 reviews

Maidenwell Cottage. Near Chesil Beach, Portland

Jan 19 – 26

G$32,628 GYD per night

Home in Dorset

4.89 out of 5 average rating, 301 reviews

Weymouth house, full of plants and near the sea

Nov 12 – 19

G$32,592 GYD per night

Guesthouse in Dorset

4.98 out of 5 average rating, 102 reviews

Palm Cottage

Sep 18 – 25

G$24,832 GYD per night

Home in Dorset

4.97 out of 5 average rating, 263 reviews

Sea View

Oct 1 – 8

G$35,710 GYD per night

Apartment in Weymouth

4.9 out of 5 average rating, 338 reviews

(Upper Deck) Beachside studio Weymouth

Jun 30 – Jul 7

G$37,811 GYD per night

Condo in Dorset

4.87 out of 5 average rating, 63 reviews

The Bolthole - only footsteps from the beach.

Sep 30 – Oct 7

G$28,520 GYD per night

Townhouse in Dorset

4.99 out of 5 average rating, 80 reviews

3 Storey, 4 bed town house, with street parking

May 21 – 28

G$23,175 GYD per night

Condo in Dorset

4.94 out of 5 average rating, 31 reviews

Beachside View

Feb 28 – Mar 7

G$27,572 GYD per night

Destinations to explore