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Dewlish Holiday Cottages

Our curated collection of Dewlish cottages has something for everyone... Whether you're idea of a great holiday is a modern glamping pod, or a rustic thatched cottage that's a hundred years old, we've got you covered! Each of our rentals features a private hot tub and everything you need for your next family holiday, romantic retreat or that getaway with a group of friends. Discover find your perfect Dewlish holiday home today.

Visitor Rating
Rating
4.8

Churn House

Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • Sleeps 12 guests comfortably
  • Multiple bathrooms available
  • Open plan living areas
  • Rural Dorset countryside location
  • Near Weymouth coastal attractions
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Visitor Rating
Rating
4.7

Manor Farm Barn

Hot Tub
Sleeps 15
Pets 1
Bedrooms: 8
  • Swimming pool for groups
  • Games room entertainment
  • Eight en-suite bedrooms
  • Peaceful village location
  • Period barn conversion
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Visitor Rating
Rating
4

The Beeches Milborne St Andrew

2 miles from Dewlish
Hot Tub
Sleeps 12
Pets 1
Bedrooms: 6
  • Sleeps 12 across six bedrooms
  • Huge kitchen-diner seats 12 guests
  • Four bathrooms including two en-suites
  • Enclosed garden with BBQ and fire pit
  • Walking distance to village pub and shop
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Ilsington Farmhouse

4 miles from Dewlish
Hot Tub
Sleeps 14
Pets 1
Bedrooms: 7
  • Sleeps 14 in seven bedrooms
  • Five-acre enclosed garden with games
  • Parking for 7+ vehicles
  • Library with snooker and piano
  • Nine miles from Jurassic Coast
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The White House

4 miles from Dewlish
Hot Tub
Sleeps 7
Pets 1
Bedrooms: 4
  • Sleeps seven across four bedrooms
  • Six car parking spaces available
  • Enclosed garden with natural stream
  • Village shop just 0.1 miles
  • Dining table seats eight people
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Piddle Inn

4 miles from Dewlish
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • Sleeps 8 in 4 bedrooms
  • Four shower rooms throughout
  • 17th-century inn conversion
  • Pet-friendly with garden terrace
  • Near Dorchester and Jurassic Coast
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Thomas Hardys Old School House

5 miles from Dewlish
Hot Tub
Sleeps 8
Bedrooms: 4
  • Historic Thomas Hardy schoolhouse setting
  • Sleeps eight in four bedrooms
  • Parking for four cars included
  • Three miles from Dorchester attractions
  • Eight miles to Jurassic Coast
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Griffin Cottage Bere Regis

5 miles from Dewlish
Hot Tub
Sleeps 6
Pets 1
Bedrooms: 4
  • Sleeps six across four bedrooms
  • Two dogs welcome with enclosed garden
  • Private parking for two cars
  • Village location near Dorset attractions
  • Recently renovated with modern kitchen
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Visitor Rating
Rating
4.2

Deer Leap House

6 miles from Dewlish
Hot Tub
Sleeps 15
Pets 1
Bedrooms: 7
  • Sleeps 15 across seven bedrooms
  • Heated outdoor swimming pool available
  • Games room with pool table
  • Tennis court with equipment provided
  • Beautiful grounds with roaming deer
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Visitor Rating
Rating
4.9

Agua de Plata

6 miles from Dewlish
Hot Tub
Sleeps 8
Bedrooms: 4
  • Lakeside home with private jetty
  • Swimming pool and gym access
  • Sleeps 8 in four bedrooms
  • Open-plan living for groups
  • Peaceful Dorset estate location
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Visitor Rating
Rating
5

Glyde House

6 miles from Dewlish
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 5
  • Sleeps 12 guests comfortably
  • Six well-appointed bedrooms
  • Multiple vehicle parking spaces
  • Large group kitchen facilities
  • Central Dorset countryside location
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Visitor Rating
Rating
4

Hardys View Lodge

7 miles from Dewlish
Hot Tub
Sleeps 8
Bedrooms: 4
  • Sleeps 8 with snooker room
  • Four en-suite bedrooms available
  • Spectacular south-facing coastal views
  • Open fires in two rooms
  • Direct countryside walking access
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Visitor Rating
Rating
4.9

Brook Cottage

8 miles from Dewlish
Hot Tub
Sleeps 10
Bedrooms: 5
  • Five spacious double bedrooms
  • Four bathrooms plus downstairs WC
  • Large kitchen with AGA
  • Two separate sitting rooms
  • Beautiful rural Dorset location
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Visitor Rating
Rating
4

Rose Farm

8 miles from Dewlish
Hot Tub
Sleeps 10
Bedrooms: 5
  • Sleeps 10 in five bedrooms
  • Three bathrooms including two en-suites
  • Games room with table tennis
  • Expansive grounds with resident animals
  • Parking for up to eight cars
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Visitor Rating
Rating
4

Crows Nest Owermoigne

8 miles from Dewlish
Hot Tub
Sleeps 10
Pets 1
Bedrooms: 4
  • Sleeps 10 with games room
  • Four en-suite bedrooms available
  • Large enclosed garden for dogs
  • Four miles from Lulworth Cove
  • Three car parking spaces included
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Visitor Rating
Rating
5

Woodbury Meadow Barn

8 miles from Dewlish
Hot Tub
Sleeps 8
Bedrooms: 4
  • Four en-suite bedrooms for eight
  • Oak-framed summerhouse with table tennis
  • Working farm with countryside walks
  • Five miles from Dorchester town
  • Rangemaster kitchen and wood burner
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Visitor Rating
Rating
5

Lamperts Dairy

8 miles from Dewlish
Hot Tub
Sleeps 12
Bedrooms: 6
  • Six en-suite bedrooms sleeping twelve
  • Dedicated games room with pool table
  • Huge kitchen-diner seats everyone together
  • Three ground floor accessible bedrooms
  • Peaceful Dorset countryside valley location
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Visitor Rating
Rating
4

Rylands

8 miles from Dewlish
Hot Tub
Sleeps 11
Bedrooms: 4
  • Sleeps 11 in four bedrooms
  • Half-acre private garden space
  • Indoor games room with PlayStation
  • Three miles from Lulworth Cove
  • Two bathrooms including en-suite
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Visitor Rating
Rating
5

Brook House

8 miles from Dewlish
Hot Tub
Sleeps 8
Bedrooms: 5
  • Five bedrooms sleeping nine guests
  • Games room with entertainment facilities
  • Wood-fired pizza oven and outdoor kitchen
  • Enclosed garden with children's play area
  • Five miles from Durdle Door
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Visitor Rating
Rating
4

Thornicks House

8 miles from Dewlish
Hot Tub
Sleeps 6
Bedrooms: 4
  • Four bedrooms sleeping six guests
  • Wood burner and cosy lounge
  • Garden room with tuned piano
  • Four miles from Lulworth Cove
  • Enclosed garden with barbecue patio
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Visitor Rating
Rating
4.2

Artists Coastal Retreat

9 miles from Dewlish
Hot Tub
Sleeps 8
Bedrooms: 4
  • Sleeps 8 in 4 bedrooms
  • Enclosed garden for children and dogs
  • Near Jurassic Coast beaches
  • Tank Museum 2.5 miles away
  • Village amenities within walking distance
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Visitor Rating
Rating
5

Old Post Office

9 miles from Dewlish
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • Hot tub in private garden
  • Four bathrooms for eight guests
  • Parking for four cars
  • Woodburning stove and underfloor heating
  • Near historic Sherborne
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Post Office Cottage

10 miles from Dewlish
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • Multiple bedroom group accommodation
  • Spacious social living areas
  • Dorset countryside location
  • Near Weymouth Beach access
  • Off-road parking available
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Old Post Office Cottage Osmington

10 miles from Dewlish
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • Grade II-listed thatched cottage
  • Sleeps eight across four bedrooms
  • Enclosed garden with summer house
  • Traditional AGA in equipped kitchen
  • Two miles from coastal paths
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Visitor Rating
Rating
4.8

Baytree Lodge

10 miles from Dewlish
Hot Tub
Sleeps 12
Pets 1
Bedrooms: 5
  • Indoor swimming pool facility
  • Games room with entertainment
  • Five en-suite bedrooms available
  • Enclosed garden with BBQ
  • Near Jurassic Coast beaches
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Visitor Rating
Rating
4.8

Fisherbridge Cottage

10 miles from Dewlish
Hot Tub
Sleeps 7
Bedrooms: 4
  • Four bedrooms sleeping seven
  • Enclosed garden with patio
  • Off-road parking two cars
  • Walking distance Bowleaze Cove
  • Fully-fitted kitchen facilities
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Visitor Rating
Rating
4.2

Waterson

10 miles from Dewlish
Hot Tub
Sleeps 7
Pets 1
Bedrooms: 3
  • Pool table for group fun
  • Stunning sea and countryside views
  • Two minutes from Smugglers Inn
  • Large garden with fruit trees
  • Direct coastal path access
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Visitor Rating
Rating
4.8

The Grain Store

10 miles from Dewlish
Hot Tub
Sleeps 7
Pets 1
Bedrooms: 4
  • Sleeps seven across four bedrooms
  • Two living rooms with Smart TVs
  • Open fire for cosy evenings
  • Safe enclosed courtyard garden
  • Walking distance to village pub
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The Downwood

10 miles from Dewlish
Hot Tub
Sleeps 16
Pets 1
Bedrooms: 8
  • Private hot tub for groups
  • Rural Dorset countryside location
  • Multiple bedrooms and bathrooms
  • Close to coast and attractions
  • Spacious open-plan living areas
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The Victorian Manor

10 miles from Dewlish
Hot Tub
Sleeps 16
  • Sleeps 16 luxury cottage
  • Heated swimming pool available
  • Private tennis court included
  • Games room entertainment facilities
  • One acre private gardens
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Big Cottages Dewlish: Your Complete Planning Guide

Big Cottages in Dewlish offer the perfect rural escape for large groups wanting authentic Dorset countryside without the hassle of coordinating multiple hotel rooms. This tiny village sits in the Piddle Valley with rolling chalk hills and ancient farmland stretching in every direction.

The location works brilliantly for family reunions and hen parties because you get proper countryside peace whilst staying within 20 minutes of Dorchester and 40 minutes from the Jurassic Coast. Properties here range from converted farmhouses sleeping 12 to massive country estates that sleep 20 or more.

Avoiding stress and planning the perfect group break

Which cottage?

Start with your absolute must-haves before browsing hundreds of holiday cottages on SnapTrip or other rental sites. We always set the budget first because large holiday houses vary wildly from cheap basic accommodation to luxury villas with indoor pools.

Location matters more than you think. Dewlish itself has no shops or pubs so you'll need cars. Check how many bedrooms versus actual guests because an 8 bed property might only have three bathrooms which creates morning chaos.

Decide on dog friendly versus pet-free early. Properties with enclosed gardens cost more but save arguments. Modern self-catering lodges offer different vibes than rustic country cottages so match the property to your group's expectations.

Plan these in advance

How many bedrooms and bathrooms for your group

Calculate one bathroom per four guests minimum. A 10 bedroom property sounds spacious until 14 people queue for two bathrooms. Check bedroom configurations too because some large groups prefer twin beds over doubles.

Bedroom allocation drama

Sort out who gets the master suite before arrival. We suggest drawing names for the best rooms or rotating if it's a long weekend. Couples usually expect double beds whilst solo guests might share twins.

Splitting costs between your group

Create a shared spreadsheet showing the rental cost per person. Factor in whether couples pay more than singles. Some groups split evenly whilst others charge per bedroom size. Decide this months ahead to avoid awkwardness.

Deposits and getting reimbursed

One person typically books and collects money from everyone else. Set clear payment deadlines because holiday lets require deposits months in advance. Use banking apps for easy tracking and send reminders without being pushy.

Hidden fees

Read the small print on heating costs during Christmas and New Year breaks. Some properties charge extra for hot tubs or firewood. Pet fees add up quickly for dog friendly cottages. Check if linen is included or costs extra per person.

Group cottage entertainment & activities

Stuff in the cottage itself - Look for properties with games rooms or cinema rooms because evenings in the countryside get dark early. Houses to rent with hot tubs provide entertainment without leaving the property. Indoor pools are rare but worth paying extra for stag dos or families with kids.

Coordinating group activities like a pro - Create a shared document with suggested activities but don't over-schedule. We find that big groups naturally split into smaller units during the day then regroup for meals. Build in flexibility rather than rigid itineraries.

Creating itineraries that please everyone - Survey your guests beforehand about interests. Some want countryside walks whilst others prefer visiting nearby Dorchester. Mix active days with lazy mornings. Schedule one big group meal but leave other times flexible.

Think about how far it is to activities or attractions - Dewlish sits centrally for exploring Dorset but you'll drive everywhere. The nearest proper town is Dorchester at 6 miles. Factor in 45 minutes to reach Weymouth beach. Cabins in isolated spots sound romantic until you're doing multiple supermarket runs.

Backup plans for when the weather's rubbish - Dorset gets proper rain so book accommodation with indoor entertainment. Properties with spacious living areas prevent cabin fever. Research indoor attractions within 30 minutes drive before arrival.

Some things to plan in advance

  • Being too isolated with no shops or restaurants nearby means bulk shopping trips to Dorchester
  • Parking inadequate for multiple cars causes daily reshuffling nightmares
  • Who organizes everything including food shops and booking group activities
  • Who's responsible if something breaks and how damages get split
  • Managing different sleep schedules when early risers wake night owls
  • Kitchen equipment for cooking meals for 14 people simultaneously
  • Bin collection days and recycling rules for the property

Top 5 group attractions in Dewlish area

The Piddle Valley and surrounding Dorset countryside offer brilliant days out for large groups wanting history and nature. Most attractions sit within 30 minutes drive making Dewlish ideal for group accommodation that balances rural peace with accessible sightseeing.

#1 Dorchester Roman Town

This historic county town sits 6 miles south with Roman walls and the excellent Dorset Museum. Groups can split between shopping and history then regroup at the many pubs and restaurants. The town works well for mixed-age parties because there's something for everyone within walking distance of the centre.

#2 Cerne Abbas and the Giant

Just 4 miles north you'll find this famous chalk figure and beautiful village. The walk up to view the giant properly takes 20 minutes and groups can grab lunch at the village pubs afterwards. It's perfect for a morning activity before heading elsewhere.

#3 Athelhampton House and Gardens

This Tudor manor house near Puddletown offers 10 acres of gardens and a stunning historic building. Large groups get discounted rates and the grounds provide space for everyone to explore at their own pace. The gardens work brilliantly for family reunion photos.

#4 Maiden Castle

Europe's largest Iron Age hill fort sits just outside Dorchester. It's free to visit and the massive earthworks impress even reluctant historians. Groups can walk the ramparts together then split up to explore. The site rarely gets crowded so you won't queue or feel rushed.

#5 Jurassic Coast Beaches

Weymouth and Lulworth Cove sit 40 minutes away offering proper beach days. Groups can hire equipment for water sports or simply claim a section of sand. The coastal cottages cost more but beach house accommodation suits summer breaks when everyone wants seaside access.

Indoor activities

Attraction What you'll experience For groups
Dorset Museum Roman mosaics and Jurassic fossils in modern galleries Self-paced exploration lets groups split by interest
Brewery Square Dorchester Cinema and restaurants in converted brewery buildings Multiple venues mean groups can eat together or separately
Athelhampton House Tudor architecture and period rooms with guided tours Group bookings available with private tour options
Tutankhamun Exhibition Dorchester Recreation of the pharaoh's tomb with authentic replicas Compact venue keeps groups together throughout visit
Local craft workshops Pottery and art classes in nearby villages Bookable for private groups wanting hands-on activities

Visitor FAQs

How many cars can we bring to Big Cottages in Dewlish?
Most large holiday houses offer parking for 4-6 vehicles but always check before booking. Properties in Dewlish often have generous parking because they're converted farms. Confirm exact numbers with the owner because street parking doesn't exist in rural villages.

Can we book cottages to rent for just one night?
Rarely. Most holiday rentals require minimum 3-night stays and week-long bookings during peak seasons. Last minute availability sometimes offers shorter breaks but expect to pay premium rates. Christmas and New Year properties typically need full week bookings.

Are properties that sleep 10 or more suitable for hen parties?
Check the listing carefully because some owners prohibit parties. Many welcome well-behaved groups but have noise restrictions and guest limits. Be honest when booking because turning up with extra people risks losing your deposit and getting evicted.

Do holiday homes in Dewlish allow dogs?
Many do because it's farming country but always verify pet policies. Some properties accept multiple dogs whilst others allow just one. Expect additional cleaning fees per pet. Properties with gardens usually specify if they're fully enclosed which matters for nervous dogs.

What's included in self-catering accommodation?
Expect fully equipped kitchens with basics like tea and coffee. Bed linen usually comes included but some properties charge extra. Towels might not be provided so check beforehand. Heating and electricity are normally included except in some older cottages during winter.

Making the most of your group break

Dewlish gives you proper Dorset countryside with enough nearby attractions to fill a long weekend or week-long break. The village itself offers pure rural peace whilst Dorchester provides shops and restaurants when you need civilization.

Book early for properties with hot tubs or indoor pools because these features get snapped up months ahead. Summer and bank holiday weekends need even earlier planning. We've found that midweek breaks offer better value and quieter attractions.

The key to successful group holidays is managing expectations upfront. Discuss budgets and house rules before anyone pays deposits. Sort out the boring logistics early so everyone can relax and enjoy the actual break together.

Unit 8, Dorset Business Park, Puddletown Road, Dorchester, Dorset, DT2 8QL