
Guesthouse holiday rentals in Chesil Bank
Find and book unique guesthouse rentals on Airbnb
Top-rated Guesthouses in Chesil Bank
Guests agree: These guesthouses are highly rated for location, cleanliness and more.

A stylish one-bedroom barn adjacent to a stream.
Developed to a high standard, Streamside sits on the edge of a quiet village, in a picturesque Conservation Area in an AONB. It is ideally situated to explore the Jurassic Coast with countryside walks/cycles via footpaths/bridal ways/turbaries from the door. With views of rolling fields in all directions and the fabulous Kings Arms Pub less than 50m away (roaring fires, wholesome food and great beer), Streamside also benefits from a private patio and a shared garden to relax and enjoy the stream
4.99 out of 5 average rating, 116 reviews
Garden Cottage, glorious Somerset countryside
Nestled in the grounds of Tarqua House in this idyllic village. Come and stay in our cosy hideaway on the Somerset/Dorset boarder close to the Jurassic Coast. A newly converted, self-contained cottage with exposed beams and underfloor heating. Super comfy kingsize double bed with mattress topper, White Co linen and towels. Fully equipped kitchenette including Smeg kettle and toaster, Nespresso coffee machine. Roberts Radio, Smart TV, Wifi. Outside space and parking. Great pub in the village.
4.98 out of 5 average rating, 261 reviews
Stunning and luxurious Manor House holiday home
This immaculate and luxurious ground floor expansive accommodation is light, airy, stylish and oozes opulence! Perfect for family, friends with a love for activities and exploring South Dorset. 10 minutes drive from Weymouth beaches, Lulworth Cove. Open plan kitchen to living area, two bedrooms, wet room, utility area, cloakroom, outstanding Orangery with garden views, private walled rear garden , enclosed coach house/ own drive in private grounds of Manor House, with direct countryside walks.
5.0 out of 5 average rating, 124 reviews
The Retreat ~ Hot Tub~ Sauna ~ Charming & Cosy Gem
Step into the stylish and comfortable 1BR 1Bath guest house nestled in the picturesque village of Tarrant Gunville. It offers a relaxing oasis with a luxury hot tub, sauna, and a perfect base to explore natural attractions and historical landmarks of Dorset County. Modern design and a rich amenity list will satisfy your every need. ✔ Comfy BR with a Double Bed ✔ Bright Living Space ✔ Kitchenette Amenities ✔ Garden ✔ Hot Tub ✔ Sauna ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Free Parking See more below.
4.88 out of 5 average rating, 212 reviews
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
4.96 out of 5 average rating, 158 reviews
Seaside studio cabin minutes from 'secret' beach
Tucked away up an unmade track & five minutes walk from a 'secret' local beach; Cove Cabin is a compact, stylish, private space; perfect for a couple or two companions. On the doorstep of lesser known beaches & gardens but not far from Weymouth's bustling scenic harbour & golden sands. Ideal stop off whilst walking the SW Coast Path. The perfect area for watersports, wild swimming, walking, mooching around the harbour & locality, sampling the local seafood & eateries & just simply relaxing.
4.94 out of 5 average rating, 343 reviews
34 Monmouth Beach
34 Monmouth Beach lies to the west of the historic Cobb in Lyme Regis. It is a beautifully finished and stylishly furnished wooden chalet right on the beach. Enjoy uninterrupted sea views from the generous wooden deck at the front of the chalet. There is parking behind the chalet and a ramped access. Our chalet is great for couples, small families and friends; it can sleep 4. Our change over days are Friday and Monday (though this listing may state Fridays only), check in 4pm, check out 10am.
4.99 out of 5 average rating, 268 reviews
Cosy Countryside 2-Bedroom Guest House
Escape to our cosy countryside annexe in Child Okeford within walking distance to historic Hambledon Hill. Set beside a peaceful stream with woodland views and birdsong, it’s perfect for a rural getaway. The self-contained space has 2 bedrooms (one with cot), a fully equipped kitchen for home cooking, and a shower room with washer and dryer. Enjoy the wood fire, private deck with grill, village shop and pubs. A peaceful home away from home to unwind and explore the charm of rural Dorset.
4.98 out of 5 average rating, 146 reviews
Garden Studio with stunning views, West Dorset.
The Garden Studio is situated at the top of our garden and nestles on the side of Hardown Hill (National Trust). It boasts spectacular views over the Marshwood Vale. Great for countryside walks around the vale and along the Jurassic Coast. Good restaurants and places of interest at nearby historic towns Bridport and Lyme Regis. Lovely beaches close by at West Bay, Seatown, Eype, Charmouth and Lyme Regis. We are approx. 2 miles from Charmouth. The Garden Studio welcomes dogs.
4.94 out of 5 average rating, 357 reviews
Characterful 2-bedroom cozy cottage with garden
Enjoy a stylish experience at this cozy, centrally-located cozy two-bedroom cottage with modern facilities plus Sky, coffee machine and private garden. Bedroom one has a double bed, bedroom two is a twin with two single beds. Walking distance from shops, cafes, Church Ope beach, cliff paths. Visit Portland to sail, dive, rock climb, bike ride, hike, visit art exhibitions, relax and explore. Unsafe for pre-school kids. Sorry no under 4 years old . No smoking 🚭
4.97 out of 5 average rating, 126 reviews
The Penthouse (Small but mighty)
Enjoy a stylish experience at this centrally-located place on the Isle of Portland. So many places to visit and all within a stones throw away from our newly refurbished Penthouse. Guest access- just off the road down a private drive with one parking space directly outside. The space- One small but stylish room with a double bed and luxury bedding. Mini fridge and kettle. En-suite modern bathroom, towels included. Check-in from 16:00pm Check out before 10:00am
4.84 out of 5 average rating, 126 reviews
Cosy lodge, parking, beautiful setting, Lyme Regis
Relax with the whole family at this peaceful place to stay. One of two properties available, Beech Lodge is situated in a quiet spot with lovely views towards the Devon countryside. It is a five minute drive to Lyme Regis and is near a footpath that takes you via Uplyme along the River Lim for a meandering walk into Lyme's centre. It is an ideal base for exploring all that Devon and Dorset has to offer. Please read our reviews. Guests love staying here.
4.96 out of 5 average rating, 256 reviewsPopular amenities for Chesil Bank guesthouses
Family-Friendly guesthouses

Cottage for two in Coombe Keynes
4.92 out of 5 average rating, 229 reviews
The Cabin
4.99 out of 5 average rating, 227 reviews
Coast, countryside and towns at your fingertips
4.97 out of 5 average rating, 407 reviews
The Cabin
4.95 out of 5 average rating, 106 reviews
The Countryside Loft in stunning rural Dorset
4.92 out of 5 average rating, 196 reviews
Milkwell’s heavenly place
4.93 out of 5 average rating, 118 reviews
The Yorkshireman @ Piddlehinton
4.96 out of 5 average rating, 223 reviews
Self-contained studio
4.98 out of 5 average rating, 154 reviewsGuesthouses with a patio

Character Barn in the Heart of Beaminster
4.94 out of 5 average rating, 168 reviews
Little Dene A lovely family friendly annexe
4.93 out of 5 average rating, 224 reviews
Old Smokey
4.99 out of 5 average rating, 129 reviews
Cosy cottage in picturesque village
4.93 out of 5 average rating, 101 reviews
Self Contained Guest Suite
4.99 out of 5 average rating, 145 reviews
Charming 2 bed self-contained cottage with Patio
4.98 out of 5 average rating, 183 reviews
Unique Private Cabin in Purbeck Dorset Countryside
4.84 out of 5 average rating, 159 reviews
The Studio @ No 28 Annexe with patio and sauna
4.86 out of 5 average rating, 159 reviewsGuest house rentals with a washing machine and dryer

Cottage with beautiful garden views
5.0 out of 5 average rating, 23 reviews
Delightful barn in scenic North Dorset
5.0 out of 5 average rating, 37 reviews
A spacious home from home in North Dorset
4.92 out of 5 average rating, 66 reviews
Stylish Private Guest Suite w/ Gym | Near Yeovil
4.98 out of 5 average rating, 53 reviews
Uplands Jurassic Guest House
4.93 out of 5 average rating, 45 reviews
Littlesea Holiday Park,Weymouth 3 bedroom sleeps 8
4.83 out of 5 average rating, 23 reviews
The Gatehouse - Friday change-overs only.
5.0 out of 5 average rating, 52 reviews
New 1 bed stable conversion in Dalwood, East Devon
4.96 out of 5 average rating, 74 reviewsDestinations to explore
- Waterfront rentals Chesil Bank
- Rentals with a hot tub Chesil Bank
- Pet-friendly rentals Chesil Bank
- Family-friendly rentals Chesil Bank
- Rentals with pools Chesil Bank
- RV rentals Chesil Bank
- Rentals with lake access Chesil Bank
- Private suite rentals Chesil Bank
- Rentals with beach access Chesil Bank
- Beachfront rentals Chesil Bank
- Condo rentals Chesil Bank
- Apartment rentals Chesil Bank
- Cottage rentals Chesil Bank
- Townhouse rentals Chesil Bank
- Bed and breakfasts Chesil Bank
- Rentals with breakfast Chesil Bank
- Hotel rooms Chesil Bank
- House rentals Chesil Bank
- Guesthouse rentals England
- Guesthouse rentals United Kingdom
- New Forest National Park
- Bournemouth Beach
- Weymouth Beach
- Paultons Park Home of Peppa Pig World
- Longleat Safari Park
- Stonehenge
- Southbourne Beach
- Boscombe Beach
- Mudeford Quay
- Brixham Harbour
- Durdle Door Holiday Park
- Torquay Beach
- The Tank Museum
- Lyme Regis Beach
- Kimmeridge Bay
- Bournemouth International Centre
- Beer Beach
- West Bay Beach
- Alum Chine Beach
- St Audrie's Bay
- Shorefield Country Park
- Highcliffe Beach
- Crealy Theme Park & Resort
- Poole Quay





