<span>Big Cottages & Group Accommodation in Portland</span>

Big Cottages & Group Accommodation in Portland

Now driving your route . . .

We can't find your location. Please try again

± {{flex}} days

We have a dedicated site for smaller properties. Take me to Snaptrip >

We have a dedicated site for pet friendly holidays. Take me to Dog Friendly Cottages >

See all deals for this weekend

Big Cottages & Group Accommodation in Portland

Portland is an island connected to the southern coast of Dorset. The island forms the southernmost point of the famous Jurassic Coast, and it's a popular destination for sports such as rock climbing, sailing, diving, and kite surfing. If you love nature and the outdoors there are many options for birdwatching from the Portland Bill Observatory. Alternatively, you can climb to the top of Portland Bill Lighthouse for fantastic views.

Here at Big Cottages, we have a great selection of big cottages in Portland to choose from for group accommodation. We have everything from rustic cottages to modern barn conversions. We even have properties with hot tubs, pools, enclosed gardens, and open fireplaces. You can use our handy search filters to find properties that you'll love. Also, thanks to our best price guarantee, you know you're getting a great deal when you book with us.

Visit the Tout Quarry Nature Reserve & Sculpture park, or visit Portland Castle for a great day out. After a long day, try The Boat That Rocks restaurant, which has lovely sea views. Portland is a great destination with plenty to do, and you'll only be a few minutes from the bustling seaside town of Weymouth with even more attractions to enjoy. See our range of big cottages in Portland for a great holiday.

Best locations for a large cottage nearby

Want to find other great destinations near Portland? Here are some of our top picks for big cottages nearby.

Read more > less >

Portland Cottages & Lodges

  • Last Minute Cottages - The Old Police Station

Dorset

The Old Police Station

Ref: S376613

Reviews 7

3
6
Fortuneswell is a picturesque village nestled on Dorset’s wonderful Jurassic Coast. The village not only boasts access to a long stretch of golden sands, but contains a vast selection of pubs, eateries and shops; making for a great seaside break....

From

£129

per night
View
  • Last Minute Cottages - The Blue Cottage

Dorset

The Blue Cottage

Ref: S700504

Reviews 4

3
7
The community of Fortuneswell is located on the Isle of Portland peninsula, connected to the mainland by Chesil Beach, a pebble spit that spans 18 miles towards West Bay, on Dorset's beautiful Jurassic Coast, now a World Heritage Site. Formerly a...

From

£87

per night
View
  • Last Minute Cottages - Pebble Reef

Dorset

Pebble Reef

Ref: S598025

3
6
Dorset's Jurassic Coast is a World Heritage Site, and the thriving community of Easton may be found near the tip of the craggy Isle of Portland Peninsula, which is connected to the mainland by the pebbled beach of Chesil Beach, which extends for...

From

£87

per night
View
  • Last Minute Cottages - House in Dorset

Dorset

House in Dorset

Ref: S229384

3
6
Situated on a one way street, the house enjoys panoramic views over Chesil Cove to Clay Ope and Chesil Beach. Reached via a causeway from Weymouth, the Isle of Portland is an unique destination, full of maritime history and quirky places. Portland...

From

£111

per night
View
1
  • Last Minute Cottages - 33 High Street

Dorset

33 High Street

Ref: S777334

Reviews 1

3
6
Situated on Dorset's spectacular Jurassic Coast, now a World Heritage Site, the village of Fortuneswell can be found on the rugged Isle of Portland peninsula, joined to the mainland via Chesil Beach, a pebble spit, which stretches 18 miles towards...

From

£95

per night
View
  • Last Minute Cottages - Jurassica House

Dorset

Jurassica House

Ref: S274177

Reviews 3

4
8
Fortuneswell can be found resting amongst the spectacularly scenic Jurassic coast, on the rugged Isle of Portland, Dorset. With a past of a quarrying area, the historic village now offers a good selection of shops, pubs and restaurants, as well as...

From

£136

per night
View
2
  • Last Minute Cottages - Cottage in Dorset

Dorset

Cottage in Dorset

Ref: S842358

3
5
Located on the picturesque Isle of Portland, the perfect base for family and friends to immerse themselves in the beauty and adventure of this unique destination. Whether you're drawn to the sparkling waters for sailing and windsurfing or prefer...

From

£88

per night
View
2
  • Last Minute Cottages - Kimberlin

Dorset

Kimberlin

Ref: S425976

Reviews 18

3
6
Portland Bill is a small promontory at the tip of the mountainous Isle of Portland peninsula, connected to the mainland by Chesil Beach, an 18-mile-long shingle spit that stretches towards West Bay. Portland Bill is located on Dorset's magnificent...

From

£81

per night
View
1
  • Last Minute Cottages - Pebbles Reach

Dorset

Pebbles Reach

Ref: S517067

Reviews 16

3
7
The village of Fortuneswell is on the rugged Isle of Portland peninsula, joined to the mainland by Chesil Beach, a pebble spit that stretches 18 miles towards West Bay. With stunning views of the Jurassic Coast and the rolling Dorset hills beyond,...

From

£85

per night
View
  • Last Minute Cottages - Sea Gem

Dorset

Sea Gem

Ref: S517329

Reviews 6

4
7
Castletown is a small village in Underhill, Dorset. It is close to Fortuneswell, on the shores of Portland Harbour, and features a sandy beach, Portland Castle, and the Weymouth and Portland National Sailing Academy. Castletown, like Portland's...

From

£128

per night
View
1
  • Last Minute Cottages - Chesil Views

Dorset

Chesil Views

Ref: S425226

Reviews 5

6
12
Fortuneswell is located on the Isle of Portland peninsula, which is connected to the mainland by Chesil Beach, a gravel spit that extends 18 miles towards West Bay. The Jurassic Coast of Dorset is a World Heritage Site. There is a decent selection...

From

£209

per night
View
LateRooms.com
  • Last Minute Cottages - Lloyds Cottage

Dorset

Lloyds Cottage

Ref: S714127

3
6

From

£155

per night
View
LateRooms.com
  • Last Minute Cottages - Mallams

Dorset

Mallams

Ref: S711494

3
6

From

£90

per night
View
LateRooms.com
  • Last Minute Cottages - The View

Dorset

The View

Ref: S637584

3
6

From

£209

per night
View
LateRooms.com
3
  • Last Minute Cottages - Neptune Cottage, PORTLAND

Dorset

Neptune Cottage, PORTLAND

Ref: S632557

3
6

From

£90

per night
View
LateRooms.com
  • Last Minute Cottages - Nordor

Dorset

Nordor

Ref: S709327

4
8

From

£420

per night
View
LateRooms.com
  • Last Minute Cottages - The Old Portland Courthouse, Portland

Dorset

The Old Portland Courthouse, Portland

Ref: S632562

4
8

From

£326

per night
View
LateRooms.com
  • Last Minute Cottages - Pebble Reef

Dorset

Pebble Reef

Ref: S661874

3
6

From

£173

per night
View
LateRooms.com
  • Last Minute Cottages - Osprey House Portland, PORTLAND

Dorset

Osprey House Portland, PORTLAND

Ref: S632576

4
8

From

£198

per night
View
LateRooms.com
3
  • Last Minute Cottages - Pebbles Reach

Dorset

Pebbles Reach

Ref: S651770

3
6

From

£103

per night
View
LateRooms.com
3
  • Last Minute Cottages - 3 bed house with amazing views & Hot Tub

Dorset

3 bed house with amazing views & Hot Tub

Ref: S732160

3
6

From

£425

per night
View
LateRooms.com
  • Last Minute Cottages - The Old Police Station

Dorset

The Old Police Station

Ref: S648381

3
6

From

£156

per night
View
LateRooms.com
3
  • Last Minute Cottages - Kimberlin

Dorset

Kimberlin

Ref: S648354

3
6

From

£161

per night
View
LateRooms.com
  • Last Minute Cottages - Sea Gem

Dorset

Sea Gem

Ref: S652068

4
8

From

£256

per night
View
Showing 1 - 24 of 46 properties

Best price guarantee

No one can beat our prices.

Best price guarantee

We partner with the largest cottage providers to offer you over 30,000 properties on one website. Our cottages are professionally managed by these partners and payments are taken by them, but rest assured, by booking via The Snaptrip Family you'll pay the lowest possible price for your trip.

We never charge you more than you would pay booking directly on the partner's site and if you become a Big Cottages member you can save even more. If you find a property priced lower anywhere else on the internet (we’d be amazed if you do), simply email us at marketing@big-cottages.com and we'll refund you the difference.

Biggest range of group accommodation

We connect you to a range of great suppliers with a huge selection of properties. We've done the research, so that you don't have to.

View properties

We get you the lowest price

We help you to complete your booking whilst giving you discounts, member only prices and our best price guarantee.

Become a member

A marketplace you can trust

We connect you with the best professionally managed properties and our marketing leading customer services can help you every step of the way.

Start your journey

Search other Portland property types

Become a Big Cottages member for free and enjoy exclusive pricing and discounts on thousands of large properties.

Login to see

  • Discounts exclusive to members
  • Save & share your favourite properties
  • See your previously viewed properties

Sign up to see

Login to see

  • Discounts exclusive to members
  • Save & share your favourite properties
  • See your previously viewed properties

Did you mean {{ suggestedEmail }}?

or

Already a member login here

Not a member?

By entering my email address, I agree to Big Cottage's Terms of Service, Privacy Policy and to receive email updates, news, & offers from Big Cottages.

Thank you for joining, member discounts are now available.

Your browser is out of date and we can't guarantee a consistent experience when using our site. Please consider updating or switching. More info on browser support