Holiday houses in Weymouth and Portland District

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Top-rated holiday rentals in Weymouth and Portland District

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Guest favourite

Guest suite in Weymouth

4.96 out of 5 average rating, 352 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.

29 Sept – 6 Oct

$1,718 AUD total

Guest favourite

Condo in Dorset

4.9 out of 5 average rating, 315 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.

12 – 19 Dec

$897 AUD total

Guest favourite

Guesthouse in Dorset

4.96 out of 5 average rating, 111 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.

11 – 18 July

$1,357 AUD total

Guest favourite

Guesthouse in Dorset

4.98 out of 5 average rating, 102 reviews

Palm Cottage

A good sized modern One bedroom garden annex only a short walking distance to local pub, take away, convenience store & hairdressers with a 20 minute walk into the Town Centre and Beach (£6 - £7 taxi ride) Weymouth is a very popular tourist attraction with numerous high end eating establishments, a superb beach and harbour which are particularly vibrant during the Spring and Summer months, a golf course and a railway station. Only 13 miles from the picturesque Lulworth Cove & Durdle Door

23 – 30 Sept

$1,278 AUD total

Guest favourite

Cottage in Easton

4.92 out of 5 average rating, 166 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.

17 – 24 Dec

$1,366 AUD total

Guest favourite

Condo in Weymouth

4.91 out of 5 average rating, 333 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.

18 – 25 Jan

$1,605 AUD total

Guest favourite

Cottage in Dorset

4.92 out of 5 average rating, 135 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.

16 – 23 July

$1,230 AUD total

Guest favourite

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.

6 – 13 Aug

$1,292 AUD total

Guest favourite

Condo in Dorset

4.97 out of 5 average rating, 137 reviews

Townhouse Flat

A lovely one bed first floor flat within family home. The flat sleeps up to 4. The flat is self-contained, but is accessed via the family home front door, hallway and stairs. The flat is on the first floor of a period townhouse on Dorchester Road, and is close to local amenities (including a Tesco Express, pub, Post Office and chip shop). The beach is a 10 min walk away and the town centre is a 20 min walk. Free on street parking is available.

12 – 19 Dec

$791 AUD total

Guest favourite

Apartment in Weymouth

4.9 out of 5 average rating, 338 reviews

(Upper Deck) Beachside studio Weymouth

A stones throw from the waters edge this studio has 270 degrees of coastal views from an elevated position (The 'crows nest' balcony! ) The windows and Private balcony have outstanding panoramic views across the Jurassic coast and Weymouth, catching beautiful sunrise and sunsets. NO NEED FOR A CAR- ITS ALL HERE! ...hikes, cycle, kayak, swim, run! Please note: Beach terrace shared with shop - can get busy in July/August period.

10 – 17 Apr

$920 AUD total

Guest favourite

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.

15 – 22 Jan

$936 AUD total

Guest favourite

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

3 – 10 Nov

$1,294 AUD total