Holiday rentals with a pool in Weymouth

Headland Hideaway Shepherd's Hut in Lyme Regis

SHEPHERDS HUT An opulent hideaway retreat nestled on the Lyme Bay headland with uninterrupted ocean views, perfect for romantics & family adventurers. With an expansive sundeck, fire pit & swimming pool & endless expanse of garden. Embark on the most charming private adventure from bedroom shepherd's hut & adjacent shower room to the architectural wonder of the glass framed kitchen, diner & sitting room with freestanding log burner & stylish interior. Sit and wonder at the expanse of ocean views

Shepherd's Hut (wood-fired hot tub/sauna optional)

Get away from it all and create romantic memorable moments in your rustic Acorn Hut. Step outside and be enveloped by nature and enjoy sitting in front of a fire pit or have a BBQ or a relaxing hot tub (EXTRA CHARGE). Acorn Hut has everything you need to stay comfortably and is particularly suited for nature lovers. Its small Hobbit wood burner will keep you snug and warm on a cold evening. Toilet/shower. Other cabins on site/ Horton Road which can be noisy at times. Hut is not fully fenced in.

Everdene shepherd's hut

Lovely views of the Blackmore Vale (amazing sunsets weather permitting!) Our huts are in a secluded area of the farm. Kingsize bed/twin beds opposite ends with curtains for privacy. Woodburner, hot/cold running water, fridge, hob, microwave, wardrobe. Picnic bench & fire pit outside. Wonderful walks, only 10 minutes on foot to village shop and pub. Great for families. Short walk to luxury wetrooms, w/m, drier. Fishing on farm. Indoor exercise pool payable locally. (Subject to availability)

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.

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

Shepherds Pye - Lakeside Retreat In The New Forest

Shepherd's Pye is a unique, 1920's Railway Carriage. Rescued from a local farm as a neglected frame, it has been lovingly restored by ourselves into a cosy, modern retreat on the edge of the New Forest. The hut is set in a secluded, private spot on our farm overlooking a lake. It is self contained and finished to a high standard; including a comfy double bed, heating, mains electrics and a fully equipped kitchen and en-suite bathroom, supplying all you need for rural yet comfortable stay.

Clover Carriage with pool, sauna and outdoor bath

Nestled into our working farm, this lovingly restored railway carriage is the perfect spot for a romantic stay away. The views are out of this world and all viewable from the large glass doors so you can stay tucked up in bed or on the sofa in front of the fire, with great wifi, free access to our beautiful heate pool & sauna (located in the pool house), beautiful walks both from the carriage or a short drive to the coast path, pub lunches, sunsets, fairy lights and a romantic outdoor bath

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

Piilopirtti - a traditional Finnish log cabin

Spend your days in a traditional Finnish log cabin with a grass roof. Step outside and be enveloped by rhododendrons and enjoy sitting in front of a fire pit or a BBQ amongst trees and nature. The main room is for sleeping and living with a super-king size bed, table, TV, 2 easy chairs. The cabin has a fully equipped kitchen and a bathroom. Cabin is not fenced in. Adjacent to Ringwood Forest where you will find a cycle trail, Moors Valley Country Park, a golf course and a lake.

The Duck House. A child/dog friendly rural chalet

The Duck House is a lovely child/dog friendly chalet nestling in the orchard at Plenty Cottage. Quiet and peaceful it's the perfect retreat for a family - and dogs are especially welcome! Open plan living it’s a comfortable and home from home. A wonderful rambling garden, summerhouse, BBQ and a (free) heated swimming pool (1st April - 31st Sept). The mantra is 'No Stress'. Ample parking, dog/child friendly pub 7 mins walk away. Wonderful NT beaches just five min drive.

Private use of Indoor Pool available May- end Sept

Self contained detached cottage in a tranquil location close to the famous 'Jurassic Coast' ; Durdle Door, Lulworth, Corfe Castle, Weymouth and Dorchester are all a short drive away. Further attractions close by are Monkey World, Bovington Tank Museum, and Sculpture by the lakes. There is a well stocked village shop and good village pub. Dorset has so much to offer, with beautiful coastline and breathtaking scenery. Relax in the pool at your leisure!