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Cottage vacation rentals in Chesil Bank

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Top-rated cottage rentals in Chesil Bank

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Top guest favorite
The cottage, constructed from Portland stone with a thatched roof, is framed by a well-maintained garden. The exterior features multiple windows and a welcoming entrance, surrounded by neatly arranged flower beds and green lawns, presenting a serene countryside setting.
Cottage in Chilfrome

Beautiful 2 bedroom cottage in glorious Dorset

Nestled in the picturesque Dorset countryside, this charming Portland stone cottage offers a quintessential English retreat. Set within the grounds of a historic Old Rectory, the property is surrounded by rolling hills, lush meadows, and the tranquil River Frome, providing an idyllic spot for a holiday. It is all on one level,we are able to rent out the whole cottage also which creates an additional 2 bedrooms for extended family - we rarely rent this out to another party and is mostly empty.

4.98 out of 5 average rating, 108 reviews
Top guest favorite
The charming exterior of a Grade 1 listed cottage is presented, showcasing a white facade with traditional windows. Stone pathing and stone planters filled with greenery add to the welcoming appearance. The neighboring cottages feature historic architectural details, enhancing the village's character.
Cottage in Cerne Abbas

Pilgrims Cottage-Luxury Grade 1 Listed cottage

Take it easy at this unique and tranquil getaway. Come and unwind in our Grade 1 listed cottage set in the most beautiful street in gorgeous Cerne Abbas. Steeped in history you won’t want to leave this hidden gem. Out the front door are walks for miles and a visit to the Giant is a must! Then either cook up a storm in the well equipped kitchen , enjoy the garden with Big Green Egg bbq or wander down to the choice of three local pubs. The Sea is just a short 30 mins drive. Parking free opposite

4.97 out of 5 average rating, 108 reviews
Guest favorite
A cottage made of natural stone is surrounded by lush greenery and colorful flowers. A spacious balcony extends over the entrance, providing an outdoor area to enjoy the views. The sun illuminates the property, enhancing its inviting presence in the serene landscape.
Cottage in Morcombelake

Romantic hillside hideaway with outstanding views

A unique and romantic hideaway, Quarryman's Cottage is dinner on the roof terrace watching the sunset over Lyme Bay & Charmouth, stargazing from the luxury freestanding bath, epic views from the double shower, reading under the old oak tree, BBQ's & firepits, leisurely walks to The Anchor at Seatown via Golden Cap or the coastal path, the sound of birdsong, the glimpse of a deer, curling up in front of the wood burner in winter. It is a tranquil & heavenly escape from the bustle of daily life.

4.95 out of 5 average rating, 498 reviews
Superhost
An indoor pool is surrounded by sleek gray tiling and illuminated by recessed lighting. The pool's inviting turquoise water reflects the ceiling lights. A cozy seating area with cushions is visible in the corner, providing a relaxed atmosphere.
Cottage in Osmington

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.

4.85 out of 5 average rating, 206 reviews
Top guest favorite
A decked seating area features two woven chairs positioned around a small circular table, overlooking a scenic view of rolling hills and green fields. The area is surrounded by a neatly trimmed hedge, creating a private and tranquil atmosphere.
Cottage in Chideock

Cottage Near Beach and 3 Pubs. South facing garden

Enjoy coastal walks straight from the door whilst staying in this stylish, cosy cottage. Lovely hill views from the garden with decked area and 3 excellent pubs all walkable from the cottage and just a 20 minute walk to the beach at Seatown. Buses every hour so you can walk one way and ride back. Spar shop with EV charging just down the road. Greenwich Cottage in Chideock is perfect for a restful break with all the mod-cons you expect with good wifi and smart TV. Cosy log-burner. Parking.

4.95 out of 5 average rating, 119 reviews
Guest favorite
A person sits in a small boat on a clear, calm waterway surrounded by lush greenery. The boat is gently gliding through the water, with vibrant foliage reflecting in the serene surface. Wildlife may be observed in this tranquil setting.
Cottage in Portesham

Pond outside your bedroom window.

Self-contained bedroom, a sitting room and shower room. Your suite of rooms is separate from the house with its own entrance. The windows overlook the village duck pond and spring and pretty waterfall. There is parking, for your car, at your door. We're in a Dorset village with Trafalgar history, centuries old church, busy pub. The coast is only a couple of miles away. We are on the Dorset Coastal Path and the SSSI Jurasic Coast. £7.50 for a full Dorset breakfast. Evening meal £7 to £12.

4.76 out of 5 average rating, 450 reviews
Top guest favorite
A modern kitchen features a wooden dining table surrounded by four woven chairs. A large range cooker is positioned against the tiled backsplash, with ample white cabinetry overhead and below. Open shelving displays glassware and decorative items, complemented by soft lighting and a neutral-colored floor.
Cottage in Weymouth

Strawberry Cottage

Lovingly restored and modernised by Harry in 2011, Strawberry Cottage is nestled by the river Wey in the village of Upwey, Dorset. This quaint property is close to the famous Jurassic Coast, within 4 miles of the seaside town of Weymouth and Dorchester town.Durdle Door / Lulworth Cove is an approximate 29 minute drive,and the main supermarket is 8 minutes away by car. Upwey has two pubs a busy tearoom,garden nursery and Tesco Express all within 5 to 10 minutes walk. Relax inside or out.

4.95 out of 5 average rating, 245 reviews
Top guest favorite
Cottage in Weymouth

Cobb Cottage - Harbourside, permit parking

Cobb Cottage is a stylish hideaway, tucked down a cobbled side street in the heart of Weymouth's historic harbour. The cottage has been lovingly converted from a former bookshop into a contemporary, centrally located holiday home with easy access to Weymouth harbour. Perfectly suited for two couples or a family, with three bedrooms and two bathrooms. There is a parking permit to for one car which provides free parking on street outside the cottage, or in a nearby car park. Dog friendly!

4.93 out of 5 average rating, 106 reviews
Guest favorite
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 in Dorset

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

4.8 out of 5 average rating, 203 reviews
Guest favorite
A private garden features a round table surrounded by four chairs, set on a stone patio. Lush greenery and flowering plants border a well-maintained lawn, while a rustic shed is visible in the background under a clear blue sky dotted with clouds.
Cottage in Lewell

Jasmine Cottage

Jasmine Cottage is a characterful, compact barn conversion, that sits next to the 400 year old farm house. It sleeps up to four people (including infants), with a double and a twin room. We are one mile away from The Wise Man Inn - an award-winning pub; 6 miles from Dorset's stunning Jurassic coast and 3 miles from the county town of Dorchester. You will, however, need a car- or bikes! Sorry, no pets and no smoking. No EV charging, yet, but there are many fast charging points nearby.

4.94 out of 5 average rating, 325 reviews
Top guest favorite
The exterior of the cottage is showcased, highlighting a charming wooden structure adorned with climbing foliage. A gravel driveway leads up to the entrance, framed by neatly arranged planters. A wooden fence enhances the privacy of the property, complemented by young trees.
Cottage in Bridport

Berry Farm Cottage

Berry Farm Cottage nestles in a private area of the grounds of Berry Farm, which dates back to the 16th century. It is located in the charming Conservation Village of Walditch, within walking distance of Bridport. The Cottage itself has 2 bedrooms and two bathrooms with an open-plan living space and is set away from the main house in its own private grounds, with 1,200sqm (0.3acres) of orchard garden, as well as an outside patio with table and chairs, with country views.

4.99 out of 5 average rating, 272 reviews
Top guest favorite
A view of Maidenwell Cottage from the garden, showcasing a landscaped area with palm trees and vibrant flowers. The cottage's exterior features a blue door and a stone wall, framed by greenery that enhances the inviting outdoor space.
Cottage in Portland

Maidenwell Cottage. Near Chesil Beach, Portland

Maidenwell Cottage is a Grade II listed period property on Portland, the southernmost point of the Jurassic Coast that has been refurbished to a high standard and designed to make you feel at home. Chesil Beach, local shops, cafes and pubs are all a within a short walking distance. Maidenwell Cottage is perfect for families and couples looking for a cosy seaside retreat and those looking for a place to relax following a day of walking, climbing and water sports.

4.99 out of 5 average rating, 336 reviews

Popular amenities for Chesil Bank cottage rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

Guest favorite
Cottage in Alton Pancras

The Hideaway - sustainable hidden gem with hottub

4.96 out of 5 average rating, 113 reviews
Top guest favorite
A thatched farmhouse is set amidst a lush green lawn, featuring vibrant flowerbeds along the front. A well-maintained garden includes wooden outdoor furniture, offering a serene space for relaxation. Large windows allow natural light to enhance the inviting exterior of the cottage.
Cottage in Dinnington

The Cottage, Parsonage Farmhouse with hot tub

4.95 out of 5 average rating, 608 reviews
Guest favorite
A charming black lodge is positioned on a grassy area, showcasing a spacious patio with a private hot tub. Sunlight filters through scattered clouds overhead, highlighting the surrounding greenery and wooden fencing that provides a sense of separation from the countryside.
Cottage in Salwayash

Exclusive Lodge with Hot Tub and stunning views

4.94 out of 5 average rating, 112 reviews
Top guest favorite
An open plan living area features a custom-built wooden four-poster bed, surrounded by ample space. A small dining table sits nearby, complemented by two lounge chairs. Large windows provide natural light, with views of the garden and wooden fence visible in the background.
Cottage in Chard

Abbey View Cottage - Scandi Hot Tub - EV Charging

4.96 out of 5 average rating, 347 reviews
Top guest favorite
The charming thatched cottage features a wooden roof terrace surrounded by lush greenery. Stonework and a blue door create a rustic appearance, while ample sunlight illuminates the exterior. A gravel pathway leads to the entrance, framed by trees and shrubs.
Cottage in Moreton

A Stunning Dorset Thatched Cottage - Dog friendly

4.95 out of 5 average rating, 205 reviews
Top guest favorite
Cottage in Dorchester

Peaceful Dorset Cottage, Hot tub, Family-Friendly

4.98 out of 5 average rating, 244 reviews
Top guest favorite
Cottage in Henley Dorchester

New Luxury Hot Tub August 2026 Shepherds Cottage

4.93 out of 5 average rating, 413 reviews
Guest favorite
A private outdoor area features a wooden hot tub surrounded by a pebble path and manicured shrubs. A small table with two chairs sits nearby, illuminated by string lights overhead. The rustic building's stone facade adds character to the tranquil setting.
Cottage in Somerset

Romantic Retreat with hot tub

4.86 out of 5 average rating, 125 reviews

Pet-friendly cottage rentals

Guest favorite
A cozy living area features a wood burner set into a simple mantel, complemented by a glass coffee table with wooden legs. Two colorful armchairs, one yellow and one teal, are arranged around the space, with natural light streaming through the windows adorned with potted plants.
Cottage in Weymouth

A Charming Cottage, Just a Moment from the Beach

4.94 out of 5 average rating, 217 reviews
Top guest favorite
Cottage in Beaminster

Blackbird Cottage near Jurassic Coast & Walks

4.92 out of 5 average rating, 166 reviews
Guest favorite
A cozy lounge area features a rustic stone fireplace with a log burner, surrounded by soft seating. A plush rug lies on the wooden floor, and framed pictures are hung on the walls. A staircase leads to the upper level.
Cottage in Portland

Milly Moll Cottage, next to Church Ope Cove.

4.91 out of 5 average rating, 268 reviews
Guest favorite
The image displays the entrance of a recently renovated cottage. A light blue door featuring a diamond-shaped window is centered. A small wall-mounted light fixture is positioned beside the door, and a mailbox is located beneath a window, framed by white walls.
Cottage in Weymouth

Violet Bay - Lovely 2 bedroom fisherman’s cottage

4.84 out of 5 average rating, 121 reviews
Top guest favorite
A light-filled lounge features a combination of two sofas, one in a rich red hue and the other in a neutral tone. A coffee table sits in front, and a white fireplace is located to the side. Decorative wall mounts add character above the sofas.
Cottage in Lyme Regis

Lyme Regis luxury - Cecilia's -3 mins from the sea

4.98 out of 5 average rating, 147 reviews
Superhost
Cottage in Weymouth

Marwells Farm Cottage

4.78 out of 5 average rating, 166 reviews
Top guest favorite
Cottage in Dorset

Beautiful character cottage in Lyme Regis

4.95 out of 5 average rating, 113 reviews
Guest favorite
Cottage in North Chideock

Authentic, cosy, thatched cottage, mins from coast

4.87 out of 5 average rating, 117 reviews

Private cottage rentals

Top guest favorite
A bright living area features a comfortable sofa with navy blue and plaid cushions, complemented by a rustic coffee table. A flat-screen TV is mounted on the wall, and natural light floods in through large windows, illuminating the stone wall and wooden furniture.
Cottage in Weymouth

Cottage close to Beach & Old Harbour with Parking

4.97 out of 5 average rating, 196 reviews
Guest favorite
A charming harbourside cottage is viewed from across the water, showcasing a two-story facade with various window styles. A small boat is docked in the foreground, while the surrounding buildings exhibit a mix of soft colors and architectural features that complement the waterfront setting.
Cottage in Weymouth

Harbour's Edge Cottage - Nothe Parade, Weymouth

4.93 out of 5 average rating, 151 reviews
Top guest favorite
The exterior of the eco-friendly lodge showcases a wooden façade with a triangular feature window. A cozy patio area is visible, furnished with a table and four chairs, surrounded by lush greenery, providing a serene outdoor space.
Cottage in Bridport

Cosy ecolodge with free parking near town & beach

4.94 out of 5 average rating, 237 reviews
Top guest favorite
A charming stone cottage is surrounded by lush greenery and various colorful flowering plants. A small white table and two chairs are placed outside, inviting guests to enjoy the garden view. The cottage features a traditional door framed by vibrant foliage.
Cottage in Dorset

Cute, Cosy & Stylish Bothy Cottage, near Sherborne

4.97 out of 5 average rating, 695 reviews
Top guest favorite
The cozy sitting area features a gray sofa adorned with decorative cushions, complemented by a round ottoman. A wooden shelf displays a vase and art, while rustic stone walls add texture. Warm lighting is provided by two wall sconces, enhancing the inviting ambiance.
Cottage in Lyme Regis

Happy Riverside Cottage by the Seaside, Lyme Regis

4.98 out of 5 average rating, 407 reviews
Top guest favorite
The exterior of The Old Mill is showcased, featuring a charming stone façade. Lush greenery surrounds the building, with a well-maintained garden visible in the foreground. Comfortable lounge chairs are positioned on the grass, inviting relaxation in this peaceful outdoor setting.
Cottage in Isle Brewers

Secluded and Romantic Paradise on Somerset Levels

4.98 out of 5 average rating, 106 reviews
Top guest favorite
The exterior of Oak Tree Barn displays rustic brick walls complemented by wooden window frames. A small tree is planted in a pot near the entrance, while a bench sits on a gravel path, surrounded by a tranquil rural landscape.
Cottage in Dorset

Lovely cosy place to stay in the heart of Dorset

4.99 out of 5 average rating, 277 reviews
Top guest favorite
A charming two-story cottage features a symmetrical facade painted in white, complemented by green accents around the entrance. The door is flanked by small windows with flower boxes. A narrow street runs alongside the building, with a parking sign positioned nearby.
Cottage in Lyme Regis

3 Bed Family cottage close to beach, Sea View.

4.96 out of 5 average rating, 270 reviews

Destinations to explore