List your home
Apply filters
£ to

27 Holiday homes in Portland

Reset search

Show results on map

Filter your search

Price per day

£ to

Bedrooms

Location

  • England Clear
  • West Country Clear
  • Dorset Clear
  • Weymouth Clear
  • Portland Clear
  • All locations

more +

less -

Also consider

Cornwall
2,983 properties
Greater London
941 properties
Cumbria / Lake District
940 properties
Devon
2,810 properties
Central England / Cotswolds
940 properties
Dorset
819 properties
Isle of Wight
507 properties
Peak District / Derbyshire
460 properties
Somerset
610 properties
Kent
557 properties
Sussex
770 properties
Norfolk
1,023 properties
Isle of Man
11 properties
Northumberland
640 properties
Yorkshire / Yorkshire Dales
1,496 properties
Coastal Cottages
222 properties
Central London/Zone 1
2,431 properties
Central London/Zone 2
1,207 properties
Newquay
616 properties
Bideford
490 properties

Filters applied: Cycling holidays (27)

To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more
27 Results  |  
14 Photos

Cottage | 2 Bedrooms | sleeps 5

Very Good 4.5/5 

3 Nights min stay

Add to shortlist

from £55 /night

£385 - £759 / week

View

Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Situated in a quiet location at the southern end of the island with stunning sea views just a stone's throw away from beautiful coastal walks and scenery - near Portland Bill lighthouse and the Lobster Pot restaurant.  …see more

9 Photos

House | 3 Bedrooms | sleeps 6

Very Good 4/5 

4 Nights min stay

Add to shortlist

from £71 /night

£495 - £660 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Pebbles view cottages is the perfect holiday destination whether you just want to get away from it all exploring the Isle of Portland or beaches of Weymouth or a more active holiday with fantastic sailing,diving rock climbing cycling and walking, portland has it all.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £38 /night

£263 - £406 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Very spacious self catering “studio style” apartment close to Portland Bill & Jurassic coastal scenery. Sleeps 2+ cot. Flexible living area. Large enclosed sun-trap patio with safe parking. Very well equipped with 32” Flat screen Sat. TV & WiFi Broadband. Pets welcome. Ideal for young/mature couples. Seating for four plus. Car unnecessary, close to walks/sailing/sports  …see more

Featured properties

20 Photos

Studio | sleeps 2

Very Good 4.5/5 

3 Nights min stay

Add to shortlist

from £42 /night

£290 - £406 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Not suitable for children
  • Car advised
  • No pets allowed
WEYMOUTH, PORTLAND, DORSET, JURASSIC COAST, CAR ADVISED, SEA VIEW, BEACH, SPA, CLIFF WALKS, SAILING, WATER SPORTS, FISHING,GOLF, ROCK CLIMBING, HORSE RIDING, BIRD WATCHING, ON-SITE CRECHE THIS APARTMENT IS SITUATED IN A STUNNING SETTING OVERLOOKING THE OCEAN AT PORTLAND BILL.  …see more

14 Photos

Cottage | 3 Bedrooms | sleeps 4

Very Good 4.5/5 

Short stays welcome

Add to shortlist

from £40 /night

£275 - £748 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Suitable for children over
  • Car advised
  • Pets welcome
Cottage newly decorated in good order dog friendly with sea views also from south facing patio looking over Chesil beach In quiet street close to all amenities buses pubs restaurant. Lovely walks along sea front and beach ideal fishing water sports dogs and swimming. Portland was the choice for the Olympic sailing venue chosen from all the places in the UK.  …see more

21 Photos

House | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £55 /night

£384 - £769 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
Very spacious self catering detached house close to Portland Bill and Jurassic coastal scenery. Sleeps up to 8 + cot in 4 bedrooms. Large enclosed family-friendly garden with safe parking. Very well equipped with 42” Flat screen Sat. TV and WiFi Broadband. Pets welcome. Ideal for families/large groups. Large, safe, grass garden. Car unnecessary, close to walks/sailing/sports.  …see more

24 Photos

Cottage | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £54 /night

£377 - £803 / week

View

Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
A traditional Portland stone property  …see more

20 Photos

House | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £61 /night

£425 - £800 / week

View

Key info:

  • Nearest beach 0 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Within sound of the breaking surf, take breakfast on the balcony and enjoy stunning views of Chesil Beach. Situated in a quiet area of Fortuneswell yet only a short walk from Shops, Restaurants, Pubs and Beach and 5 minutes from the Olympic Sailing Venue.  …see more

28 Photos

House | 3 Bedrooms | sleeps 7

Very Good 4.5/5 

3 Nights min stay

Add to shortlist

from £69 /night

£477 - £1556 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Seagull House in Portland Chesil Beach  …see more

17 Photos

House | 4 Bedrooms | sleeps 10

Very Good 4.5/5 

2 Nights min stay

Add to shortlist

from £43 /night

£300 - £1365 / week

View

Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
A new spacious detached house with a safe, secluded and walled garden. Situated in a prime position on top of the island with spectacular rural and sea views looking towards Dorset's Jurassic Coast. Ideally situated in the centre of the County of Dorset.  …see more

16 Photos

House | 3 Bedrooms | sleeps 8

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £36 /night

£250 - £1190 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Contemporary Cottages are ideally situated for anyone visiting Weymouth and Portland and Dorset. Short breaks & weekly bookings are accepted throughout the year. You can book from any day of the week and flexible arrival and departure times can be arranged by request. Situated very near to Weymouth & Portland National Sailing Academy & in centre of Dorset's Jurassic Coast  …see more

24 Photos

Studio | sleeps 2

Very Good 4.5/5 

3 Nights min stay

Add to shortlist

from £47 /night

£325 - £395 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Not suitable for children
  • Car not necessary
  • Pets welcome
Open all year. Tranquil, warm retreat above Church Ope Cove. Self catering Studio for 2 set on the cliff path a 7 minute walk from the nearest village and major amenities. Comfy four poster bed (new pics coming soon) Wet room, Wifi, Woodburner, Ipod dock. Pet welcome. Suits romance and retreat, sail, walk, climb, work or study with Wifi, Pets and walkers Welcome Awards.  …see more

17 Photos

House | 2 Bedrooms | sleeps 6

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £43 /night

£300 - £660 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Hillside is a stunning fully refurbished Victorian house with views from a southwest facing garden overlooking Portland Harbour and WPNSA.Only five minutes walk from Chesil beach, Hillside was refurbished to be our home which we have chosen to allow others to enjoy. What other property on Portland has chandeliers ,roll top bath and feature wallpaper?  …see more

23 Photos

Cottage | 3 Bedrooms | sleeps 4

Very Good 4.5/5 

2 Nights min stay

Add to shortlist

from £38 /night

£260 - £690 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car advised
  • Pets welcome
A character terraced cottage, on a quiet street in the village of Fortuneswell on the Isle of Portland, only a few minutes walk from the famous Chesil Beach, 5 minutes drive from the National Sailing Academy and easy walk ing distance to the Olympic Sailing Village. Excellent restaurants and pubs within walking distance of the cottage. Free Wi-Fi.  …see more

22 Photos

House | 2 Bedrooms | sleeps 5

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £89 /night

£620 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Stunning location with probably the best sea views on Portland. Attractive 2 bedroom house with gardens and easy parking, next to open hillside with uninterupted views of Weymouth Bay, the ocean and coastline. Close to great beaches, sailing, shops, pubs and restaurants Only 5 minutes from the National Sailing Academy. Ideal situation for exploring Portland's natural heritage.  …see more

6 Photos

Cottage | 2 Bedrooms | sleeps 4

1 night min stay

Add to shortlist

from £43 /night

£295 - £495 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Suitable for children over
  • Car advised
  • No pets allowed
Cosy two bedroom cottage in the heart of Fortuneswell, Portland.  …see more

8 Photos

Cottage | 4 Bedrooms | sleeps 8

Very Good 4/5 

7 Nights min stay

Add to shortlist

from £65 /night

£450 - £625 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Mallams Cottage is a beautifully finished period cottage, well located for Chesil Beach, Portland Harbour and the National Sailing Academy. Close to the best sailing waters in Europe.  …see more

5 Photos

Cottage | 2 Bedrooms | sleeps 4

1 night min stay

Add to shortlist

from £65 /night

£450 - £550 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Suitable for children over
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
If you were much closer you would be in the sea!!  …see more

8 Photos

Cottage | 3 Bedrooms | sleeps 4

Very Good 4/5 

Short stays welcome

Add to shortlist

from £58 /night

£400 - £550 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Suitable for children over
  • Car advised
  • No pets allowed
  • Private garden
A charming cottage in this pretty road, a short walk down to Chesil Beach and Cove and easy going of the National Sailing Academy at Portland Harbour.  …see more

8 Photos

House | 4 Bedrooms | sleeps 10

Short stays welcome

Add to shortlist

from £72 /night

£500 - £900 / week

View

Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Whether you are looking for that relaxing break, or here to sail or just time with the family this charming cottage would suit your needs. Nestled off Wakeham, you will agree this cottage is a real find. This deceptive very comfortable house offers home from home facilities with everything to entertain a family  …see more

8 Photos

Cottage | 3 Bedrooms | sleeps 7

7 Nights min stay

Add to shortlist

from £58 /night

£400 - £550 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Character cottage over three floors, sleeps seven comfortably. A short walk from Chesil Beach and the local amenities, the National Sailing Academy and Portland Harbour. The harbour is found within a short drive or leisurely walk from the property. At the centre of the Jurassic Coast, Portland is an ideal base for water sports, walking & exploring Dorset.  …see more

10 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £65 /night

£450 - £625 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
Frigate Apartment is a stunning holiday apartment with sea views situated in the eye-catching Ocean Views development, close to Portland Harbour and the National Sailing Academy. The development boasts a state-of-the-art health and fitness centre complete with an indoor swimming pool.  …see more

8 Photos

Cottage | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £58 /night

£400 - £550 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
4 Sea View offers the best of modern comforts with period character in a cottage just a short walk from the splendors of Chesil Beach & Cove on the Isle of Portland Dorset. Offering a fabulous kitchen and comfortable accommodation.  …see more

10 Photos

Cottage | 3 Bedrooms | sleeps 5

Short stays welcome

Add to shortlist

from £58 /night

£400 - £550 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Suitable for children over
  • Car advised
  • No pets allowed
  • Private garden
Fabulous sea views from this cottage just a few minutes from Chesil Beach.  …see more

11 Photos

House | 4 Bedrooms | sleeps 8

Very Good 4.5/5 

Short stays welcome

Add to shortlist

from £72 /night

£500 - £675 / week

View

Key info:

  • Nearest beach 1 km
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
This well presented holiday house has a large and sociable open plan living area with kitchen, seating and dining areas, allowing for a relaxed and inclusive holiday atmosphere.  …see more

20 Photos

House | 4 Bedrooms | sleeps 10

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £69 /night

£480 - £900 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
The Gift House is a beautiful fully renovated and refurbished 4 bedroom house situated 2 minutes walk from the beach, with stunning panoramic sea views from all reception rooms and bedrooms stretching across Chesil Beach to the Olympic Sailing Village. The property is suited to outdoors enthusiasts and families. A perfect retreat with modern luxuries.  …see more

8 Photos

Cottage | 3 Bedrooms | sleeps 8

3 Nights min stay

Add to shortlist

from £71 /night

£495 - £946 / week

View

Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
The perfect base for a beach side holiday. We are close to the National Sailing Academy and a short walk to the Castletown diving centre. The Cove House Inn is a 300 yard walk along the beach and has a lovely atmosphere and good food.  …see more