Pet-friendly vacation rentals in Chickerell

Your hideaway on Weymouth harbourside!

Harbour Hideaway....light and airy lower ground floor apartment with own courtyard in fantastic harbourside location. Permit parking for 1 car & dogs welcome for free! Main sandy beach 5 mins away and town is just across the bridge. NB/ there are two single beds in the bedroom and a drop down King Size bed in the lounge (not in a separate room). My second Airbnb is up the hill behind Hideaway & the reviews are lumped together by Air so that explains them! It's a sleep 6 house but no pets allowed

Summer Lodge

The Summer Lodge boasts uninterrupted views of the Fleet Lagoon and world famous Chesil Beach from its elevated position on the South West Coast Path (Jurassic Coast). 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. Our sea view lodge sleeps 6 people. There are 2 double bedrooms and a small double sofa bed.

A luxury unique home spa - White Stones Retreats.

Set in a prime position amidst a quintessential village of thatched cottages. Where wildflower paths and trickling streams amble down the the beautiful Osmington Bay. Toe dipping in the shallows, coastal walks under flaring sunsets, hibernating in our home spa while storms crash outside. Our unique holiday home offers a sanctuary in all weathers. With a collated & collected vibe, this light filled cottage is perfect for families looking for a beach escape, only a 5 minute drive to the sea.

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Guest favorite

Enchanting Manor Coach House

An elegant, relaxed home in the grounds of the Manor in this AONB with walks directly from the house. The pretty village of Winterbourne St. Martin (Martinstown) has a great pub and a super village shop both within a short walk. Close to the Jurassic Coast and spectacular country views, its the perfect place to chill after a walk, a day at the beach (approx five miles away) or visiting the many attractions in and around Dorchester. Guests have a private garden, and access to a tennis court.

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.

Cobb Cottage - Harbourside, permit parking

Cobb Cottage is a stylish hideaway, tucked down a cobbled side street in the heart of Weymouth's historic harbour. The cottage has been lovingly converted from a former bookshop into a contemporary, centrally located holiday home with easy access to Weymouth harbour. Perfectly suited for two couples or a family, with three bedrooms and two bathrooms. There is a parking permit to for one car which provides free parking on street outside the cottage, or in a nearby car park. Dog friendly!

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Guest favorite

Stunning Barn conversion +heated pool (15/5-15/9)

Courage Cottage is a two bedroom detached barn conversion in a Georgian farmyard.The barn was converted in 2013 so has all modern conveniences including underfloor heating. It is very individual and situated in a quiet , rural setting. It has two bedrooms with en-suite bathrooms. The village of Martinstown has an excellent pub and shop. Dorchester is 2 miles away and has every facility including good rail connections in all directions.Swimming pool (shared ) open May 15th-Sept 15th

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Guest favorite

A Charming Cottage, Just a Moment from the Beach

Right on the gateway of the best beach in the United Kingdom. This is an excellent place to get your Weymouth adventure underway. Sympathetically updated and located a moment from the beach and train station; it'll suit most visitors needs. We've tried to update the cottage in keeping with a turn of the century victorian home, yet keeping it stylish and up to date with all the mod-cons you would expect. We're located close-by, so we're on-hand to support your trip. Enjoy.

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.

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Guest favorite

Captain's Quarters Apartment

Just a short stroll from Weymouth’s award-winning beach, this stylish retreat is near shops, restaurants, and the train station with links to London. Recently refurbished, it features a cozy bedroom with a double bed and a living room with a sofa bed. Step onto the decked balcony to unwind with fresh sea air. Please note: As a traditional 1910s building in a central town location, occasional outside noise and some sound from neighbouring properties may be audible.

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Guest favorite

Spacious luxury home | 200m from beach | parking

Set on a quiet street close to everything, this renovated Victorian townhouse offers a calm, comfortable place to settle in and relax. Guests often mention how clean, stylish and genuinely homely it feels. With generous living space and thoughtful touches throughout, it suits both families and groups of friends. You’re just a short walk from the station, beach, harbour, shops, cafés and restaurants, making it an easy, well-equipped base for a laid-back coastal stay.

"The Escape" 2 bed property 100m from beach ..

Location, Location, Location! The Escape is nestled right in the heart of Weymouth, a few minutes walk from the beach, shops, pubs and restaurants. This beautiful refurbished 2 bedroom 2 bath maisonette can sleep up to 5 comfortably, perfect for a family holiday or couple/s enjoying a short break . Bedroom 2, has a King size bed and a single bed. Nearby carparks. A permit can be arranged at extra cost. Parking is not guaranteed.