Family-friendly vacation rentals in Chickerell

Batch Hut (Dog Friendly but just one please)

Wooden clad hut set in the heart of Upwey village, it’s similar to a Shepherd's Hut but slightly bigger. The hut is sited in a field only 3 minutes walk from two local pubs, set on the Jurassic Trail so country walks in abundance, 5 min drive to Weymouth Beach. This is ideally suited for those wanting down to earth but acceptable accommodation. Everybody who has stayed here has really enjoyed the country setting and although basic I have been told many times that the photos don't do it justice.

Flat One The Beaches

New for 2026 parking permit for Zone F on street parking The apartment is in a central position & can be noisy in the evenings especially at the weekends Recently converted Grade II listed property on Weymouth seafront. The apartment is one of four located off a private inner courtyard on the first floor. well equipped apartment across the road from Weymouth’s award winning beach and nestled a stones throw away from Weymouth town with its great choice of harbour side restaurants and bars.

Blue Bay Cottage - Cove Street, Weymouth Harbour

Beautiful 3 bedroom cottage close to Weymouth harbour and town centre. Own entrance leading to dining room, kitchen, conservatory, cloakroom and rear courtyard. Stairs to lounge with gas stove, bathroom with large shower and single bedroom. Further stairs to master bedroom and twin bedroom. Kitchen with integrated dishwasher, fridge, Neff hide and slide oven, microwave. The cottage has gas central heating and a parking permit for on street/harbourside parking. WiFi and outside space to sit

The Cosy Crab Cave - Steps from Weymouth Harbour

Tucked one street behind the bustling main harbour at the heart of Weymouth is where you’ll find The Cosy Crab Cave. Less than 5 minutes walk from the beach and even closer to a plethora of pubs, restaurants and cafes, our location is ideal whether you’re after a lively beach weekend on your doorstep or a stepping stone to explore the rest of our idyllic county Dorset. A self contained apartment with private entrance, master bedroom and additional submarine room - ideal for 2 and cosy for 3!

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

Home from home

Enjoy a stylish experience at this centrally-located accommodation. Coming with a friend but don’t want to share bed, bed settee available, request when booking. Nature reserve within a minute walk, off main road but short walking distance to beach, shops, pubs and local buses. Off road parking for 1 car, small outside seating area to enjoy your morning cuppa or evening drinks. Self contained with own front door. Stair lift on request, bathroom has low level access shower, handrails and seat.

The Snipe House with Hot Tub

Set on the Jurassic coast in an area of outstanding natural beauty. Snipe House offers access to a beautiful scenic part of Dorset. Situated just 5 minutes from Abotsbury and 10 minutes from Weymouth close to award winning beaches and convenient access to many miles of glorious country walks. Private, secluded exclusive. The House is situated on a dog boarding site. Snipe House comes with your own private dog run, we can also offer doggy day care. Luxury Spa set at 38C so unwind and chill.

A luxurious modern 3-bedroom Swift Bordeaux

A luxurious modern 3-bedroom Swift Bordeaux Silver Prestige. This fabulous caravan is situated at Haven Littlesea Holiday Park in Weymouth in a spacious plot with views of the Fleet Lagoon and Chesil Beach. Sleeps up to 6 people. 1.5 bathrooms Linen and towels supplied. Parking spaces for 2 cars. Outside decking and seating area. Onsite restaurant, laundrette and local shop. For use of swimming pool, entertainment venue and booking activities you can purchase Play Passes from Haven

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

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.

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.

Seaview Self-Catering-Fossils Reach

Modern double bed studio with bath/shower room and open plan kitchen/lounge situated on a working farm. Beautiful seaviews over the fleet and jurassic coast. Only 2 miles from Weymouth beach and a few strides from the south west coastal footpath. We are in walking distance of 5 public houses and restaurants and have ample parking. If your here for the breathtaking seaview walks or the attractions that weymouth has to offer you have found the right place.