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Holiday rentals with a pool in Chickerell

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Chickerell

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Superhost
The interior features two twin beds with colorful bedding arranged against wooden walls. A dining table is set with two glasses of red wine, a bottle, and a small vase of flowers. A window offers views of the surrounding greenery.
Shepherd’s hut
4.89 out of 5 average rating, 196 reviews

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)

Top guest favourite
A serene outdoor seating area is highlighted, featuring two wicker armchairs with soft cushions and a glass-topped table. Beyond, the tranquil Fleet Lagoon reflects sunlight, providing picturesque views, while colorful flowers add a touch of warmth to the setting.
Chalet
4.96 out of 5 average rating, 233 reviews

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.

Guest favourite
An indoor pool area is presented under a wooden-beamed ceiling, featuring exposed brick walls. Soft lighting creates a calm ambiance around the clear water of the pool. A cozy seating area is visible in the background, adding to the overall relaxation space.
Home
4.86 out of 5 average rating, 129 reviews

Large coastal cottage with spa and private pool

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.

Top guest favourite
An inviting outdoor dining area is nestled beside a serene swimming pool. A glass table is set with plates and cutlery, surrounded by comfortable seating adorned with patterned cushions. Lush greenery and flowering plants create a relaxing atmosphere.
Home
4.96 out of 5 average rating, 26 reviews

East Creek, beach, pool, dog, hot tub - Ringstead

East Creek in Ringstead is newly refurbished with a brand new kitchen, lounge and bathroom. This house sleeps 10, has fast broadband and has fantastic views. Step onto your expansive deck, where panoramic views of the azure sea stretch endlessly before you. This is the ultimate vantage point for coastal bliss. Your own private pool awaits, inviting you to cool off in style or soak up the sun in absolute privacy. Swimming pool open May to end of September, for 2025 trailing end of October.

Top guest favourite
A modern caravan is positioned on a spacious grassy plot. It features a large deck with white railing and a series of windows providing ample natural light. The exterior is clad in light-colored panels, and nearby caravans are visible in the background.
Chalet
4.94 out of 5 average rating, 109 reviews

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

Guest favourite
A spacious corner sofa is adorned with colorful cushions in yellow, gray, and blue. A cozy navy blanket drapes over the side. A wooden coffee table holds a selection of brochures, with natural light filtering through sheer curtains at the nearby window.
Home
4.85 out of 5 average rating, 120 reviews

Spacious Caravan near sea Weymouth Bay Haven

Our holiday home is spacious with a well equipped kitchen. Located 12-15min flat walk (buggy friendly) from the seaside. The Haven park offers a swimming pool, live entertainment and play areas for kids until 14th November (access to indoor complex is an additional fee on a first come first serve basis) We are opposite the activity field. One car parking space next to the caravan.. CHANGEOVER DAYS ARE MONDAY OR FRIDAY. Please contact us to make a shorter booking or with any questions.

Guest favourite
A charming barn conversion features natural stone walls and large windows that invite ample sunlight. The surrounding landscape includes lush greenery and a clear blue sky, creating a serene rural atmosphere. The driveway leads to the entrance, providing easy access to the property.
Cottage
4.8 out of 5 average rating, 198 reviews

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

Guest favourite
Bungalow
4.89 out of 5 average rating, 73 reviews

The Granary

Benefit from far reaching views over rolling countryside from both the living area and master bedroom. The Granary is a charming contemporary conversion perfect for modern day living with its exposed beams and relaxed styling. Downstairs, you’ll find a farmhouse style dining table for four, and two large comfortable sofas around the TV. A fully equipped galley kitchen leads off this area. Sleeps 4 across a King size bed and 2 single beds. 550m walk from the descent to Durdle Door.

Top guest favourite
A renovated railway carriage features a wooden deck, framed by lush grass and potted plants. Outdoor seating arrangements include a circular table and two chairs, contributing to a welcoming atmosphere. Large glass doors open up to a bright interior, framed by decorative flower pots.
Train
4.99 out of 5 average rating, 343 reviews

Foxglove Carriage with pool, sauna & 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 heated pool and sauna in the pool house, beautiful walks both from the carriage or a short drive to the coast path, pub lunches, sunsets, fairy lights and romantic outdoor bath.

Guest favourite
A charming cottage is set amidst a lush garden, featuring well-tended greenery and colorful shrubs. The building's white exterior is complemented by a slate roof, with trees casting gentle shadows over the expansive, manicured lawn under a clear sky.
Flat
4.93 out of 5 average rating, 293 reviews

The Duck Wing, quirky dog friendly apartment

The Duck Wing is a quirky, self contained apartment on the first floor within Plenty Cottage. It's beautifully appointed for a relaxed, carefree stay in a wonderfully rural environment. Nothing is too much trouble. It sleeps two in double bed in a pretty bedroom and has a double sofa bed too. Own bathroom/shower, a separate WC and a warm spacious living area. The pub is 7 mins walk away and the beaches a 5 mins drive. The private, heated swimming is available 1st April - 31 Sept

Top guest favourite
An indoor swimming pool is featured, surrounded by large windows allowing natural light. The ceiling beams reveal a spacious, airy atmosphere. Two red chairs are positioned nearby, and a shallow end is visible with steps leading into the water. A blue cover rests along one side of the pool.
Cottage
4.98 out of 5 average rating, 387 reviews

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!

Guest favourite
A solid wood cabin is nestled among lush greenery and vibrant flowering shrubs. Tall trees surround the cabin, providing a sense of seclusion while allowing natural light to filter through the leaves. A warm, inviting entrance with a lantern enhances the rustic charm.
Cabin
4.9 out of 5 average rating, 165 reviews

Woodpecker Lodge - Log Cabin with Private Hot Tub

Each solid wood log cabin is encircled by trees for your privacy yet open enough to let sunlight through. We aim to give you that cosy, romantic log cabin retreat experience with a solid wood burner, private hot tub and free access to our seasonal outdoor heated pool (end May - Sept). If the dates you require are already booked, please look at our other cabins: Nuthatch Lodge, Tawny Owl Lodge, Hedgehog Lodge (all with private hot tubs) or Roe Deer Lodge.

Popular amenities for Chickerell rentals with a pool

Quick stats about holiday rentals with a pool in Chickerell

  • Total holiday rentals

    Explore 30 holiday rentals in Chickerell

  • Nightly prices starting at

    Chickerell holiday rentals start at ÂŁ52 per night before taxes and fees

  • Verified guest reviews

    Over 530 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Wifi availability

    20 of Chickerell holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chickerell rentals

  • 4.8 Average rating

    Chickerell stays are highly rated by guests – averaging 4.8 out of 5!

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