Portland Private Holiday Homes

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Portland holiday homes

A spacious loft with high ceilings, exposed wooden beams, and large windows.

1. The Old Portland Courthouse

Portland

RM6,738 total

includes taxes & fees

29 Oct - 30 Oct

A dining area with a table set for four, a bottle of wine, and a bowl of fruit.

2. Weybury Cottage

Rodwell

RM3,745 total

includes taxes & fees

30 Oct - 31 Oct

A modern kitchen with stainless steel appliances, wooden countertops, and a herringbone floor pattern.

3. 15 Hardwick Street

Weymouth Town Center

RM4,782 total

includes taxes & fees

30 Oct - 31 Oct

A corner room with a bay window overlooking a beach, two leather chairs, and a small ottoman.

4. Low Tide

Weymouth Town Center

RM8,472 total

includes taxes & fees

4 Nov - 5 Nov

A stone house with a sloped roof, a wooden door, and a gravel driveway.

5. The Courthouse

Weymouth

RM4,587 total

includes taxes & fees

6 Nov - 7 Nov

A view from a room with a glass door leading to a balcony with a wooden railing.

6. Village View

Bridport

A modern two-story house with a sloped metal roof and a white facade.

7. 8 Driftwood

Bridport

kevin

RM2,458 total

includes taxes & fees

31 Oct - 1 Nov

A wooden table with a bottle, glasses, and a newspaper, set under a beige umbrella on a patio with a view of the sea.

8. Seacliff

Bridport

Vicki

RM5,049 total

includes taxes & fees

31 Oct - 1 Nov

View all properties

Find holiday rentals that suit your style

Apartments

Cottages

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Portland Hotel Reviews

Sleeping Bear Hotel Dorchester

10/10 Excellent

"This is a lovely hotel - the building itself is full of character with plenty of space throuhgout. With free hot drinks and a vending machine for snacks, soft drinks and some alchoholic ones too, there is no need to rush out - but literaly within a stone's throw are 2 restaurants and 2 pubs - and for powerfully-armed cricketers - a couple of cafes. Our limited interactions with the staff found them all to be very helpful and friendly. A huge thank-you to all."

The Bull Hotel

10/10 Excellent

"We recently stayed in the Bull hotel and opted for a delux room. WE are so glad we did as the room was wonderful. very impressed, The stairs to the upper floors may be a challenge for the less mobile but I was told there a few rooms on the ground floor, one of which is deluxe. The hotel is convenient for the main shopping area and has a vety useful parking area to the rear of the hotel. All the staff were very helpful and friendly. A good breakfast and evening meal. The outside seating looked good too. A great place to stay in a lovely town."

Heights Hotel

8/10 Good

"Very friendly and welcoming staff on arrival. Nice Reception area, but once you get beyond the reception the corridors and our room (203) were somewhat austere. Nice breakfast, but a wider selection of fresh fruit salad would be very welcome. The red berries were still frozen but the cooked breakfast was nice, plus a good choice of teas and coffee. Fabulous views over Chesil Beach from the restaurant, but the view from our room was compromised by the double glazing having condensation between the panes of glass (plus a net curtain for privacy). I would stay here again purely for the view and convenience of being where we needed to be (on Portland)"

The Jubilee Hotel West- with Spa Facilities

10/10 Excellent

"The room was a good size, we had a family room for 5. The room was clean and tidy and good amenities in the room itself. The best aspect was the seaview which was fantastic helped by some good October weather. We didn't use the bar much as we were visiting relatives who live in Weymouth - but it looked good with plenty to do. The best thing about staying in the older hotels on the front is access to the beach/Weymouth centre, room size and view. Overall very happy with the hotel and the price. Would definitely stay again - thanks."

Find out more about Portland