Pet-friendly holiday 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

Authentic, cosy, thatched cottage, mins from coast

Cosy Carters Cottage nestles in the peaceful Dorset hamlet of North Chideock, adjacent to 16th century Home Farm Cottage. A fab rambler's location, with EV charger, 40 mins walk from the Jurassic coastline, 3 thatched pubs, Spar shop, Felicity's Farm Shop, Hell's Lane smugglers hollow-way, Colmers Hill & Symondsbury Estate Cafe. 15 mins drive to Lyme Regis. The cottage is simply furnished - 2 bedrooms, (second at top of stairs) WC, kitchen & lounge. Guest parking with private, walled garden.

The Snug - 2mins walk from the beach 🏝

Moments from Weymouth beach this lovely self catering apartment is perfectly located. Dorset is breathtaking with its Jurassic coast, explore popular spots like Lulworth cove or the isle of Portland or stay put and enjoy all that Weymouth’s bustling town, harbour and beaches have to offer. With great seafood, and a wonderful selection of restaurants within walking distance you won’t be at a loss of places to eat. Take a rib ride from the harbour and see if you can spot our resident dolphins.

The Old Reading Room West Stafford

The Victorian Reading Room of West Stafford is of historical importance. Used before the war as a Reading Room for the villagers and estate workers, the newspapers were provided, the village shop in the late 1930s, then a workshop and a store room for the church. We have now lovingly restored, decorated and furnished this amazing building into a cosy self catering holiday retreat, "far from the madding crowd" Open plan, comfy double sofabed, wood burner, country walks and fabulous village pub.

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.

Discover Little Drey: Your Perfect Getaway

At Little Drey, you'll find comfort, and warm hospitality, all while being conveniently close to Dorchester. A variety of restaurants, cafes, and shops are all within walking distance. Close to some of the best places to visit in Dorset, and within easy reach of famous beauty spots and amazing places to visit. Parking on property along with self-check-in, makes it super easy to have a relaxing, enjoyable break. Your host lives next door and is on hand to make your stay the best possible.

Stunning Barn conversion with heated swimming pool

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

Marwells Farm Cottage

Beautiful countryside Cottage, located in a rural setting on the river Wey. Local walks from your doorstep, Short car journey to Weymouth sea front. Self contained annexe with private entrance. Fully fitted galley kitchen. One bedroom with a double and single bed+ sofa bed in the sitting room. Children of all ages welcome. I am pet friendly, with felines of my own. Wi-Fi is available but very limited due to rural location. Free on site parking. All photographs taken in January 2026

Primrose Shepherds Hut

This hut is called Primrose. King size bed with 100% cotton linen, with a choice of pillows. Kitchen with a microwave/grill, small fridge and hob. Underfloor heating. Full size shower and toilet within the hut. Outside shelter for washing dogs/boots and facilities for bike washing on site. Private parking and enclosed garden with out door seating. Welcome pack provided. Famous Jurassic Coast Lulworth Cove and Durdle Door, Monkey World and the Tank Museum are close.

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 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.

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 step. 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.