Vacation rentals with breakfast in Isle of Portland

The Old School House Annexe

Our Annexe is a peaceful and quiet space situated in the semi rural area of Upwey in Weymouth. It is the perfect spot to recharge your batteries, it is fully equipped, clean and comfortable. We have an inside Entertainment area which guests are welcome to use with a hot tub, tv and darts board and comfortable seating for chilling. There is also a Woodburner oven for guests use. Fantastic local walks on the doorstep and good local amenities with Weymouth town, beach and shops 10 mins drive.

Cosy private Loft overlooking Dorset countryside

Nestled in the heart of the Dorset countryside, The Loft is your ideal 'getaway'. From stunning views to a comfy king-size bed, this cosy space will provide you with everything you need to relax. Open the stable door, and listen to the birds, reconnect with nature while sipping coffee and tucking into a selection of breakfast options provided upon your arrival. With an abundance of local amenities, please see the guide for my favourite secret spots! We look forward to welcoming you!

Stunning Beachfront 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.

Garden View Annexe near West Bay, Bridport.

Our light bright garden view annexe is ideally situated for enjoying all that the Jurassic coastline has to offer. The harbour at West Bay (setting for ITV’s drama Broadchurch) is a pleasant 10 minute walk away. The bustling historic town of Bridport is only 5 minutes by car or about 25 minutes on foot. There you will find a twice weekly street market, a variety of shops and a good choice of pubs and cafes. Both Bridport Leisure Centre and the Golf Club with driving range are nearby.

Little House at the Seaside.

Quiet and peaceful residential area within a mile of Weymouth beach and SW coast path, bird reserves, parks and town centre with private off-road parking space 50m away. Within 2km of 4 main supermarkets and 5 minutes walk from local shops. Great as a snug cosy retreat in winter. Excellent seafront restaurants are within walking distance. Local attractions include Sealife Centre, Abbotsbury Sub-tropical gardens, Chesil Beach, Portland Bill and Thomas Hardy’s Dorchester.

A charming one bedroom guesthouse nr Maiden Newton

The Woodshed is a self contained guesthouse that is situated in a paddock behind our main house and in the heart of the glorious Dorset countryside, perfect for holidays and short breaks. A lovely one double bedroom property with secure private parking and a decking area with outdoor seating and stunning views of the Frome valley. Surrounded by rolling hills and close to some of Dorset's most treasured landmarks, this is a place to truly escape and relax. *NO PETS

The Seaside Shepherd’s Hut

Fall asleep to the sound of waves on shingle in this stunning, hand-crafted oak shepherd’s hut. In winter the Hut is cosy with double glazing, a wood burner plus radiator. In summer relax on the deck to enjoy glorious views of Lyme Bay on the World Heritage Jurassic Coast. Nestling in my garden, Chesil Beach and the South West Coast Path are 30 seconds away down a private path. Watch magnificent sunsets over the bay and enjoy stargazing in our dark skies.

Delightful 1 bedroom cabin/ 'sleep out'

Located in the picturesque 18th century village of Milton Abbas, the cabin is situated on the edge of a forest within our garden There are beautiful places to walk or cycle and we are very close to the historical Milton Abbey and chapel The village has a gastro pub , a shop and post office and tea rooms There are also other pubs close by which all provide food All bedding , towels and tea towels provided Check in after 15.00 Check out before 11.00

Cosy Hut in Woodland with breakfast

3 nights for the price of 2! Tucked away in its own private woodland, our off-grid Shepherd’s Hut offers a peaceful escape surrounded by nature. Fall asleep to the sound of the stream and owls calling, and wake to birdsong and dappled light. With a cosy coal burner, comfy bed and star-filled skies above, it’s the perfect place to unwind after exploring the coast, visiting RSPB Arne or walking the Purbeck hills. Pure Dorset magic. 🌿✨

The Long Barn

Stone and oak barn in the grounds of a grade II listed farmhouse. The space is light and airy, it has 2 bedrooms and so is ideal for families or two couples. Well behaved dogs are accepted. Although separate from the farmhouse, it is not self-contained, as there are no cooking facilities, other than a fridge, kettle and toaster. Breakfast provisions are provided for guests to have at their leisure.

The Haven Garden room Weymouth

We offer 1 double bedroom with a doorway leading to your breakfast area which includes a. fridge, kettle + toaster. We supply a cold continental style breakfast daily to the breakfast area leaving you then to decide when you would like to eat. The bathroom which is in the main house (approx 6 metres) is exclusively for guests and accessible along a short pathway. (See photos)

Lake View Classic Sailing boat on private lake

Beautiful Lake view classic boat moored on a private lake. Set in the heart of the Jurassic coast world heritage site. Private decking area is right on the waters edge. There is a private bathroom within 5 meters of the boat. The lovely town of Wareham is only a 20 minute walk with numerous pubs, restaurants and shops.