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Greenhill Holiday Cottages

Our curated collection of Greenhill 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 Greenhill holiday home today.

Visitor Rating
Rating
4.9

Weymouth Bay Apartment B

Hot Tub
Sleeps 7
Pets 1
Bedrooms: 3
  • Stunning sea views to Portland
  • Sleeps 7 in 3 bedrooms
  • Garage parking space included
  • 2 minutes walk to beach
  • Dog-friendly with secure garden
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Visitor Rating
Rating
4.9

Weymouth Bay Apartment C

Hot Tub
Sleeps 7
Pets 1
Bedrooms: 3
  • Stunning sea views from bedrooms
  • Just 2 minutes to beach
  • Sleeps 7 across 3 bedrooms
  • Secure garage parking space
  • Shared garden for groups
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Visitor Rating
Rating
4.7

Milton Manor

347 miles from Greenhill
Hot Tub
Sleeps 33
Pets 1
Bedrooms: 14
  • Georgian mansion sleeps 33
  • Hot tub and games room
  • 14 bedrooms 14 bathrooms
  • Beautiful walled gardens
  • Near Stourhead and Longleat
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Visitor Rating
Rating
4.9

Chase House

347 miles from Greenhill
Hot Tub
Sleeps 15
Pets 1
Bedrooms: 7
  • Sleeps 15 across seven bedrooms
  • Hot tub and sauna facilities
  • Medieval hall with oak panelling
  • 7000 acre estate with golf
  • Japanese pavilion retreat experience
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Visitor Rating
Rating
4.9

Royal Oak House

350 miles from Greenhill
Hot Tub
Sleeps 12
Bedrooms: 7
  • Swimming pool with pool house
  • Seven bedrooms sleeping 12 guests
  • Games room with entertainment
  • Two acres of private grounds
  • Parking for 10 cars
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Visitor Rating
Rating
4.8

The Stable House

351 miles from Greenhill
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • Hot tub in private courtyard
  • Pool table and table tennis
  • Sleeps 8 with enclosed garden
  • Three bathrooms, well-equipped kitchen
  • Near Sherborne, welcomes three dogs
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Visitor Rating
Rating
4.9

The Gully

351 miles from Greenhill
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • Hot tub and games room
  • Sleeps 8 with 3 bathrooms
  • Six off-road parking spaces
  • Welcomes up to three dogs
  • Six miles from Sherborne attractions
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Visitor Rating
Rating
4.8

Samstone

351 miles from Greenhill
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • Outstanding countryside views
  • Ground floor accessible bedroom
  • Dual kitchen setup
  • Spacious rooms throughout
  • Beautiful peaceful location
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Visitor Rating
Rating
4

The Farmhouse At Coking Farm Fishery

351 miles from Greenhill
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • Spacious farmhouse for large groups
  • Peaceful fishing ground setting
  • Multiple vehicle parking spaces
  • Close to Stourhead and Longleat
  • Pet friendly Dorset countryside retreat
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Visitor Rating
Rating
4.9

Hillside Cottage

352 miles from Greenhill
Hot Tub
Sleeps 10
Pets 1
Bedrooms: 5
  • Wood-fired hot tub
  • Five ensuite bedrooms
  • Open-plan group living
  • Countryside wildlife views
  • Near Shaftesbury attractions
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Visitor Rating
Rating
4.9

Dukums House

353 miles from Greenhill
Hot Tub
Sleeps 8
Bedrooms: 4
  • Sleeps 8 in 4 bedrooms
  • Private wood-fired hot tub included
  • Games barn with table tennis
  • Countryside walks from the door
  • Near Shaftesbury and Longleat Park
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Visitor Rating
Rating
4

Heron Lake Cottage

355 miles from Greenhill
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • Indoor heated swimming pool access
  • Sleeps 8 in 4 bedrooms
  • Play area and football pitch
  • Two lakes in extensive grounds
  • Wood burner and open-plan living
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Visitor Rating
Rating
4.4

Moles Cottage

357 miles from Greenhill
Hot Tub
Sleeps 16
Pets 1
Bedrooms: 8
  • Sleeps 16 across 8 bedrooms
  • All bedrooms have en-suites
  • Parking for 7 cars
  • Museum Inn next door
  • Enclosed garden for pets
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Visitor Rating
Rating
4

Old Orchard Melbury Osmond

358 miles from Greenhill
Hot Tub
Sleeps 7
Pets 1
Bedrooms: 4
  • Sleeps seven across four bedrooms
  • Games room with table tennis
  • Large enclosed garden for dogs
  • Two bathrooms plus ground floor WC
  • Six miles from Sherborne attractions
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Visitor Rating
Rating
4

Rose Farm

358 miles from Greenhill
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
4.9

Brook Cottage

358 miles from Greenhill
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
5

Old Post Office

358 miles from Greenhill
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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Visitor Rating
Rating
4

Stonehaven

359 miles from Greenhill
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • Sleeps 8 in 4 bedrooms
  • Parking for 4 cars
  • Split-level garden with BBQ
  • Pet-friendly welcomes 2 dogs
  • Walking distance to village pub
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Visitor Rating
Rating
4.8

Newfield Farm Cottages

359 miles from Greenhill
Hot Tub
Sleeps 20
Pets 1
Bedrooms: 10
  • Three separate barn conversion cottages
  • Games room with entertainment facilities
  • Sleeps 20 across 10 bedrooms
  • Parking for 8+ cars included
  • Ground floor accessible accommodation
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Visitor Rating
Rating
4

Poppy Cottage

361 miles from Greenhill
Hot Tub
Sleeps 7
Pets 1
Bedrooms: 4
  • Four bedrooms sleeping seven
  • Enclosed garden space
  • Woodburning stove feature
  • Central Beaminster location
  • Off-road parking included
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The Victorian Manor

362 miles from Greenhill
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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The Downwood

362 miles from Greenhill
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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Visitor Rating
Rating
5

Stapleford Farm

363 miles from Greenhill
Hot Tub
Sleeps 20
Pets 1
Bedrooms: 10
  • Sleeps 20 across three cottages
  • Games room with pool table
  • Gym and fitness facilities
  • Beautiful Dorset countryside views
  • Shared courtyard with barbecue
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Drackenorth

363 miles from Greenhill
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • Sleeps 12 guests comfortably
  • Multiple bathrooms for groups
  • Fully equipped group kitchen
  • Beautiful Dorset countryside location
  • Easy access coastal attractions
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Bower Cottage

363 miles from Greenhill
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • Traditional Dorset cottage character
  • Spacious group accommodation available
  • Peaceful countryside location setting
  • Near Jurassic Coast attractions
  • Multiple bedrooms and bathrooms
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Visitor Rating
Rating
4

Lower Pound Farm

363 miles from Greenhill
Hot Tub
Sleeps 9
Pets 1
Bedrooms: 4
  • Sleeps 9 in 4 bedrooms
  • Stunning sea and valley views
  • Extensive gardens with play equipment
  • Wood burner in inglenook fireplace
  • 5 miles to Jurassic Coast beaches
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Visitor Rating
Rating
4.4

The Cow Shed

363 miles from Greenhill
Hot Tub
Sleeps 15
Pets 1
Bedrooms: 9
  • Nine en-suite bedrooms
  • Nature reserve location
  • On-site visitor centre
  • Ground floor accessibility
  • Private grounds access
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Visitor Rating
Rating
4

The Farmhouse

363 miles from Greenhill
Hot Tub
Sleeps 8
Bedrooms: 4
  • Sleeps 8 in rural Dorset setting
  • Large enclosed garden with climbing frame
  • Two cosy wood burners provided
  • Exceptionally well equipped throughout
  • Four miles from Lyme Regis beach
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Visitor Rating
Rating
4

Dairy Cottages Big Barn

363 miles from Greenhill
Hot Tub
Sleeps 8
Pets 1
Bedrooms: 4
  • Four en-suite bedrooms sleeping eight
  • Open-plan living with vaulted ceiling
  • Outdoor kitchen with plancha grills
  • Enclosed garden and shared paddock
  • Near Bournemouth and New Forest
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Visitor Rating
Rating
4

The Cheese House

364 miles from Greenhill
Hot Tub
Sleeps 10
Pets 1
Bedrooms: 4
  • Sleeps 10 in four bedrooms
  • Games barn with table tennis
  • Grade II* listed 15th-century farmhouse
  • Large enclosed garden with BBQ
  • 2.5 miles from Charmouth beach
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Big Cottages Greenhill: Your Complete Planning Guide

Booking Big Cottages in Greenhill gives you the perfect base for a memorable group break with space and facilities that hotels simply can't match. This charming Dorset village sits near Weymouth and offers stunning coastal views alongside peaceful countryside that makes it ideal for large groups seeking both adventure and relaxation.

You'll find everything from spacious holiday homes with hot tubs to massive properties that sleep 20 or more guests. The area combines easy access to the Jurassic Coast with local amenities and attractions that cater brilliantly to family reunions and celebrations of all kinds.

Avoiding stress and planning the perfect group break

Which cottage?

Start with your must-haves before browsing through hundreds of properties on Snaptrip and other rental sites. Set your budget first because large holiday houses vary wildly in price depending on season and facilities. Location matters hugely when you're coordinating big groups.

How many bedrooms and bathrooms do you really need? A 10 bedroom property sounds massive but might only have three bathrooms which creates queues every morning. Distance from the nearest town affects your food shopping options and restaurant choices significantly.

Pet-friendly or pet-free makes a huge difference to your search results. Dog friendly cottages with enclosed gardens are brilliant for families bringing their pets but some guests prefer properties without animal access. Modern or rustic changes the entire feel of your stay and impacts heating costs during winter breaks.

Plan these in advance

How many bedrooms and bathrooms for your group

Calculate one bathroom per four guests as a minimum for comfortable group accommodation. An 8 bed cottage needs at least two full bathrooms plus a downstairs toilet. Properties that sleep 12 should ideally have three bathrooms to avoid morning chaos.

Bedroom allocation drama

Decide who gets the master suite before you arrive to prevent awkwardness. Couples with young children often need ground floor rooms whilst elderly relatives benefit from ensuite facilities. Discuss sleeping arrangements openly when booking cottages for 10 or more guests.

Splitting costs between your group

Use apps like Splitwise to track who pays what throughout your stay. Some groups divide the rental equally whilst others charge per bedroom based on size and facilities. Agree the method before anyone transfers deposits.

Deposits and getting reimbursed

One person typically books and collects money from everyone else. Set clear deadlines for payment because holiday lets and lodges require deposits months in advance. Bank transfers work better than cash for tracking contributions to your group cottage rental.

Hidden fees

Check if electricity and heating cost extra during winter. Some self-catering properties charge for firewood and hot tub usage. Cleaning fees and damage deposits add significantly to the total cost of houses to rent for big groups.

Group cottage entertainment & activities

Stuff in the cottage itself - Look for properties with games rooms and large dining tables that seat everyone together. Villas with pool tables and cinema rooms keep teenagers entertained during downtime. An indoor pool transforms a rainy weekend into something special for families.

Coordinating group activities like a pro - Create a shared document where everyone suggests activities they'd enjoy. Vote on must-do experiences versus optional extras. Book popular attractions weeks ahead especially for Christmas and New Year breaks when availability shrinks fast.

Creating itineraries that please everyone - Build in free time because not everyone wants constant activity. Split into smaller groups for different interests rather than forcing everyone to do everything together. Stag dos and hen party groups need different planning approaches than family reunions.

Think about how far it is to activities - Check actual driving times to beaches and attractions because rural country cottages can be further from amenities than you expect. Coastal cottages by the sea offer immediate beach access but might be distant from inland attractions.

Backup plans for bad weather - Dorset's weather changes quickly so have indoor alternatives ready. Museums and leisure centres work brilliantly when outdoor plans fail. Properties with hot tubs and spacious living areas save the day during storms.

Some things to plan in advance

  • Being too isolated with no shops or restaurants nearby limits your food options significantly
  • Parking inadequate for multiple cars causes daily frustration when guests can't access vehicles easily
  • Who organizes everything including food shopping and activity bookings needs deciding upfront
  • Who's responsible if something breaks should be clear before arrival to avoid disputes
  • Managing different sleep schedules matters when early risers clash with night owls in open-plan spaces

Top 5 group attractions in Greenhill

Greenhill and the surrounding Weymouth area offer fantastic attractions for large groups seeking variety. The location combines maritime heritage with natural beauty and family-friendly venues that work brilliantly for groups of all ages throughout the year.

#1 Weymouth Beach

This award-winning sandy beach stretches for miles and provides space for big groups to spread out comfortably. The shallow waters make it perfect for families whilst the promenade offers cafes and amusements. Beach accommodation nearby means you can walk there in minutes from many holiday rentals.

#2 Nothe Fort

This Victorian coastal defence fort offers interactive exhibits and stunning harbour views that engage all ages. The maze of underground passages fascinates children whilst adults appreciate the historical significance. Groups can explore at their own pace with plenty of space for everyone.

#3 SEA LIFE Weymouth

The aquarium features sharks and sea turtles alongside local marine life in well-designed exhibits. Group rates make it affordable for large holiday parties and the indoor setting works perfectly regardless of weather. Interactive feeding sessions and talks happen throughout the day.

#4 Lodmoor Country Park

This nature reserve combines walking trails with a children's play area and miniature railway. Big groups appreciate the free entry and varied terrain that suits different fitness levels. The RSPB reserve section attracts birdwatchers whilst kids enjoy the adventure playground.

#5 Brewers Quay

This converted Victorian brewery houses shops and the Timewalk museum exploring Weymouth's history. The covered complex works brilliantly for groups on rainy days with cafes providing meeting points. The mix of retail and heritage appeals to diverse interests within large groups.

Indoor activities

Attraction What you'll experience For groups
SEA LIFE Weymouth Marine exhibits with sharks and interactive displays Group discounts available and suitable for all ages
Nothe Fort Victorian fort with underground passages and exhibitions Self-guided tours let groups explore at own pace
Brewers Quay Shopping and museum in historic brewery building Multiple activities under one roof for varied interests
Weymouth Pavilion Theatre shows and entertainment venue Large capacity for group bookings and events
Hollywood Bowl Weymouth Ten-pin bowling with arcade games Lane bookings accommodate parties and competitive fun

Visitor FAQs

How far in advance should we book Big Cottages in Greenhill?
Book six to twelve months ahead for peak season and Christmas breaks. Last minute availability exists but limits choice significantly. Properties that sleep 14 or sleeps 20 get reserved fastest because there are fewer of them.

What's the minimum stay for large cottages?
Most require three nights minimum with seven nights standard during summer. Weekend breaks and one night stays are rare for big houses. New Year and bank holidays often have longer minimum stays.

Are cheap options available for large groups?
Off-season rates drop considerably between November and March excluding holidays. Midweek bookings cost less than weekends. Splitting costs between guests in a 5 bedroom or larger property works out cheaper per person than hotels.

Can we hire properties for parties?
Many large holiday homes prohibit parties explicitly in their terms. Some properties to let welcome celebrations if you inform them beforehand. Damage deposits increase for group events and noise restrictions apply.

What facilities should we prioritize for group accommodation?
A large dining table that seats everyone together matters most. Multiple bathrooms prevent queues. Gardens provide outdoor space whilst properties with hot tubs add luxury. Good WiFi keeps everyone connected.

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