Holiday rentals in Weymouth and Portland District

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Top-rated holiday rentals in Weymouth and Portland District

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Home in Portland
4.96 out of 5 average rating, 124 reviews

Blue Skies Retreat,Modern house Chesil Beach

Modern semi-detached house located two minutes walk from Portland Marina and Chesil beach. Perfectly situated for divers, walkers sailors and anyone who pursues water based activities. Pubs restaurants and takeaways within walking distance of the house. Private parking situated at the front of the property. This house has a modern contemporary interior with two double bedrooms. One of these with twin beds. Enclosed rear garden with patio and seating area perfect for watching the Chesil sunset.

Top guest favourite
A round porthole window features a serene view of calm waters reflecting the sky. A distant rocky shoreline with palm trees can be seen on the left side, framed by a textured wooden wall.
Bungalow in Dorset
4.95 out of 5 average rating, 230 reviews

Islands Wrest (The Galleon Rm). Pet friendly.

Nautical galleon themed room with own entrance, kitchen & shower room this your own space within owner occupied property. Explore Portland, an Island that features breathtaking views, beautiful walks. Castles, 3 lighthouses. Chesil beach. a Museum, rock climbing, wildlife, water sports. History of smugglers & pirates explore Church Ope Cove. 20 min on bus to Weymouth for more seaside fun! Set centrally on the Jurassic coast. This is a real hidden gem. Not suitable for infants (Adults only)

Top guest favourite
An exterior view of the cabin shows double doors opening onto a private deck, surrounded by bamboo fencing and potted plants. A small table with a chair is positioned on the deck, providing a welcoming entry to the stylish interior.
Guest house in Dorset
4.94 out of 5 average rating, 315 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.

Superhost
A modern penthouse terrace features a spacious outdoor deck that seamlessly transitions into the bright living area. Expansive glass walls invite natural light, while the inviting interior includes comfortable seating and greenery. The serene sky above is visible, adding to the tranquil setting.
Apartment in Bournemouth
4.85 out of 5 average rating, 188 reviews

The Beach Hytte - Stunning Sea View Penthouse

Enjoy your perfect getaway in this award winning 2 bed penthouse apartment with 180 degree sea views in the heart of the tranquil Alum Chine area of Bournemouth just a few minutes walk from the beach. The property boasts two dining areas, one of which sits on the large balcony with views across Bournemouth beach and a bespoke wood burning stove for the winter nights. The open plan kitchen leads onto a cozy living room where you can enjoy Sky Glass TV entertainment through super fast WiFi.

Top guest favourite
Apartment in Dorset
4.97 out of 5 average rating, 213 reviews

Townhouse Flat

A lovely one bed first floor flat within family home. The flat sleeps 4, max 5 with z bed. 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 (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. See additional charges for Z bed hire.

Superhost
A sandy beach stretches along the coastline, meeting gentle waves as they roll ashore. In the background, tall cliffs rise sharply, contrasting with the open sky that holds scattered clouds. Small figures can be seen enjoying the beach, while a few distant structures are perched on the hillside.
Cottage in Sutton Poyntz
4.83 out of 5 average rating, 187 reviews

A peaceful retreat to rest, recharge and explore.

A cosy self-contained Annex with open plan living area, log burner and character wood floor and stone walls. A spiral staircase leads up to a very comfortable double bedroom with a king-size bed. The bedroom on the ground floor contains a double bed and enjoys patio doors leading onto a small private garden with patio table and chairs. The property is hidden away in a very quiet, peaceful setting and is entered from the gravel drive through the front door into the light airy kitchen.

Top guest favourite
Apartment in Dorset
4.91 out of 5 average rating, 139 reviews

Beachside View

Enjoy easy access both beach and town centre from this beachfront couples' retreat. This top floor (3rd floor) flat has panoramic views across the bay and there's even a telescope. This apartment is right next to a M&S food hall and within 100m of a fish n chip shop, a Chinese takeaway, a traditional pub and several bars and restaurants. There is a king size bed in the bedroom and a sofa that pulls out into a bed in the lounge. Access to the bathroom is through the bedroom.

Guest favourite
Tiny home in Portland
4.92 out of 5 average rating, 215 reviews

Breeze - White Stones Studios

Come and enjoy unique contemporary eco-friendly accommodation set in peaceful and creative surroundings at the heart of Easton, Portland, on the tip of The Jurassic coast. Located to the rear of White Stones Art Cafe's secluded and tranquil gardens there are three holiday studios available, each sat nestled together in peaceful surroundings. Breeze is one of our three bespoke holiday studios, finished to a high standard and providing a contemporary holiday experience.

Guest favourite
Home in Dorset
4.93 out of 5 average rating, 107 reviews

The Palms at No10 - Spacious and Family Friendly

Welcome to the Palms at No10! Unwind in this stylish and beautifully appointed home for your stay on the Jurassic Coast. The property offers ample space for 6 guests across three stunningly finished bedrooms, and our outdoor terrace provides al fresco to unwind after a day exploring everything Dorset has to offer. The Palms is perfectly located for a coastal getaway, with both the town centre just a short 20 minute walk away and the seaside only a stones throw away.

Guest favourite
The exterior view showcases a stone-clad building with a welcoming entrance. A small window and a hanging planter add charm. A pathway leads to the door, with a black chair positioned nearby for outdoor seating.
Guest house in Dorset
4.86 out of 5 average rating, 106 reviews

The Penthouse (Small but mighty)

Enjoy a stylish experience at this centrally-located place on the Isle of Portland. So many places to visit and all within a stones throw away from our newly refurbished Penthouse. Guest access- just off the road down a private drive with one parking space directly outside. The space- One small but stylish room with a double bed and luxury bedding. Mini fridge and kettle. En-suite modern bathroom, towels included. Check-in from 16:00pm Check out before 10:00am

Top guest favourite
A welcoming lounge area features a red sectional sofa and a circular dining table with black chairs. A brick feature wall houses a mounted TV above a cozy fireplace. Lush greenery and a small potted plant add subtle touches of nature to the space.
Flat in Dorset
4.97 out of 5 average rating, 138 reviews

The Bunker • Stylish Coastal Stay • Walk to Beach

Stay close to everything in this stylish apartment, just a short walk from Weymouth’s beach and town centre. The area is breathtaking, with the Jurassic Coast and iconic spots like Lulworth Cove and the Isle of Portland nearby. Weymouth’s harbour, restaurants, cafés and coastal paths are all within easy reach, making it a great base for exploring. Complimentary tea, coffee, some biscuits and toiletries are provided to help you settle in on arrival.

Guest favourite
A hot tub is positioned beneath a blue canopy, featuring brick walls that enhance the rustic setting. Two round, green topiary plants are placed on either side of the steps leading to the tub, which is surrounded by a tranquil outdoor area.
Holiday home in Easton
4.93 out of 5 average rating, 225 reviews

Quirky 2 bed holiday home with hot tub and sauna.

Newly built 2 bedroom cottage with hot tub and sauna located in Easton on Portland in Dorset. This unique home is built in Portland stone and has a ground floor outdoor space with patio and outdoor oven area as well as having an upstairs outdoor mezzanine area with bi-folding doors. The main living space that includes a 90” smart television. Both bedrooms have super king beds and are en-suite with doors to outside access and large smart tv screens

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