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Compare 168 Vacation Homes in Portland with updated reviews, rates, and availability.

Luxury Detached House and Grounds, also benefits from full disabled facilities.
Property grounds
Luxury Detached House and Grounds, also benefits from full disabled facilities.
9.4 out of 10, Exceptional, (65)
"Perfect property for our trip with teens, grandparents, extended family and our 2 well behaved dogs. Wonderful space, facilities and views. Host very attentive and excellent communication. We needed somewhere we could access with a wheelchair abd this property was well designed for easy access, a lift and multiple wet rooms. Enjoyed large family dining and quality time in the open planned living space. Highly recommend !"
Luxury Detached House and Grounds, also benefits from full disabled facilities.
Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight
Views over the valley from bedroom
Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight
9.6 out of 10, Exceptional, (58)
"We have stayed here many times before. The cottage is perfect."
Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight
Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)
Room
Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)
9.8 out of 10, Exceptional, (31)
"Lovely stay in the Farm house, plenty of room for everyone. The grandchildren loved seeing the horses and plenty of open space for them to run around. Thanks for a very enjoyable stay."
Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)
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Stunning 1-bedroom coach house with free parking
Dining
Stunning 1-bedroom coach house with free parking
9.6 out of 10, Exceptional, (5)
"Georgous coach house, beautiful decor and had eveything you needed. It was very clean and just lovely. Annabelle, th host, couldnt have been more helpful. Would love to stay here again."
Stunning 1-bedroom coach house with free parking
3 Bed Holiday home close to idyllic Lulworth Cove
Exterior
3 Bed Holiday home close to idyllic Lulworth Cove
10.0 out of 10, Exceptional, (3)
"This property is in a perfect position in the beautiful village of West Lulworth. It is very spacious and comfortable with plenty of outdoor space for kids to run around. Practically everything is provided (BBQ charcoal, kitchen roll, coffee pods etc) and the local Londis is about 10 minutes' walk away. The reason I only gave 4 stars for accuracy of description is that I think the website undersells it. It is ideally situated for trips out to places such as Lulworth Castle (well worth a visit,...
3 Bed Holiday home close to idyllic Lulworth Cove
Seafeathers - Luxury Holiday Home with Sea Views
Decking
Seafeathers - Luxury Holiday Home with Sea Views
Seafeathers - Luxury Holiday Home with Sea Views
Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast
Exterior
Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast
10.0 out of 10, Exceptional, (75)
"The cottage is so comfortable, well-located, and well-equipped. I could not have asked for a better experience. Thank you!"
Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast
Beautiful, family friendly Cottage with sea views of Chesil Beach
Room
Beautiful, family friendly Cottage with sea views of Chesil Beach
9.6 out of 10, Exceptional, (14)
"Had a lovely time good central location. Nice place to stay better than a B&B"
Beautiful, family friendly Cottage with sea views of Chesil Beach
escape the ordinary - private self catered group holiday stay
Property grounds
escape the ordinary - private self catered group holiday stay
10.0 out of 10, Exceptional, (1)
"We had a lovely long weekend at the Piddle Inn. Downstairs is just like a pub - all for us! Bar, games room and pub kitchen fantastic for a family group. Gorgeous bedrooms and the sound of the stream at night. Lovely walks straight from the back and Alan the host, was incredibly helpful and friendly."
escape the ordinary - private self catered group holiday stay
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
wonderful view from first floor veranda
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
10.0 out of 10, Exceptional, (38)
"Spacious and clean with incredible views. We thoroughly enjoyed our week here. Promises a lot and delivers more. A pleasant walk into Weymouth and close to Portland. We hope to be back."
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
2-9 AUG AVAILABLE Coastal House with Sea Views Nr Sea & Sandy Beaches
STUNNING DETACHED HOUSE WITH INCREDIBLE SEA VEWS NEAR SUPERB BEACHES
2-9 AUG AVAILABLE Coastal House with Sea Views Nr Sea & Sandy Beaches
10.0 out of 10, Exceptional, (84)
"the house was perfect our a work team of 7. The flexibility of the bedrooms was amazing as we could have some of the beds split into twin beds. Fantastic living room with lots of space. Thoughtful Welcome Pack was also available there when we arrived. Everything we could possibly need was in the kitchen and simple instructions for things that we needed to know. Beautiful walks literally across the road. We would not hesitate to stay again."
2-9 AUG AVAILABLE Coastal House with Sea Views Nr Sea & Sandy Beaches
Perfect little hideaway 3 minutes walk to the beach. One minute to the station.
Living area
Perfect little hideaway 3 minutes walk to the beach. One minute to the station.
8.0 out of 10, Very Good, (1)
"Beds and sofa very comfortable. A very nice touch to have lego and a range of dvd's for adults and children, also the children's story books a great idea too!"
Perfect little hideaway 3 minutes walk to the beach. One minute to the station.
DO NOT BOOK THIS LISTING. I CANNOT CANCEL IT ON VRBO BUT I'M CLOSED
Property grounds
DO NOT BOOK THIS LISTING. I CANNOT CANCEL IT ON VRBO BUT I'M CLOSED
DO NOT BOOK THIS LISTING. I CANNOT CANCEL IT ON VRBO BUT I'M CLOSED
Barn conversion, quiet location and heated swimming pool ( from mid May)
Barn conversion, quiet location and heated swimming pool ( from mid May)
9.4 out of 10, Exceptional, (57)
"Fantastic property. Great location. Clean, with all the necessary facilities and utilities."
Barn conversion, quiet location and heated swimming pool ( from mid May)
Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea
Bedroom 3
Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea
9.0 out of 10, Wonderful, (42)
"Very nice and i will stay again"
Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea
Luxury coastal property with private indoor pool.
Interior
Luxury coastal property with private indoor pool.
10.0 out of 10, Exceptional, (7)
"This is a beautiful house, well equipped and was really suitable for our holiday with three generations of family. The pool was a big hit with the children in particular and the adults enjoyed the hot tub, sauna and steam room. The beach at Weymouth together with all of the attractions are within easy reach. This was a very enjoyable week."
Luxury coastal property with private indoor pool.
Entire home hosted by Lisa
Exterior
Entire home hosted by Lisa
10.0 out of 10, Exceptional, (9)
"This is our second stay at this home and it was just as lovely. The location next to church Ope beach is wonderful; Lisa is an excellent host; and the house is homely, stylish and well-equipped. We loved it!"
Entire home hosted by Lisa
Two Bedroomed Bungalow at Cove Holiday Park
Lounge with sea views
Two Bedroomed Bungalow at Cove Holiday Park
9.8 out of 10, Exceptional, (74)
"The property is lovely, clean and well equipped in a great location. Great communication for arrival."
Two Bedroomed Bungalow at Cove Holiday Park
5 minutes walk to the beach. 6 bedroom 6 bathroom house, parking for 2/3 cars.
Living area
5 minutes walk to the beach. 6 bedroom 6 bathroom house, parking for 2/3 cars.
10.0 out of 10, Exceptional, (2)
"The Grange was a great property for our large family of 11 to stay for a week. 6 bedrooms, each with their own attached bathroom with shower, was extremely convenient for our family. The back garden was a nice bonus as well. The house was in a good location that was walkable to the beach, shopping, Sealife, and other activities. Harriet was great to work with and a wonderful host. Would recommend this property to others in the future."
5 minutes walk to the beach. 6 bedroom 6 bathroom house, parking for 2/3 cars.
Private detached cottage to rent on Chesil Beach
Exterior
Private detached cottage to rent on Chesil Beach
10.0 out of 10, Exceptional, (59)
"We loved our week at Greenbanks. We have stayed in many holiday homes over the years and loved pretty much all of them, but Greenbanks is an absolute star. The location is delightful and so quiet, which is great. The house is beautifully furnished and very homely. It is made extra special by the mentions and photos of Gt. Uncle Edgar and Aunt Marian and all the family books and furnishings. The kitchen is exceptionally well equipped with just about everything you need and all of it is high...
Private detached cottage to rent on Chesil Beach
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Portland

Sunseeker Renagade 60ft in Weymouth. Perfect to explore the Jurassic Coast.
Marina
Sunseeker Renagade 60ft in Weymouth. Perfect to explore the Jurassic Coast.
10.0 out of 10, Exceptional, (1)
"Had a wonderful stay on this beautiful boat, extremely clean and tidy with all the amenities you could hope for. Excellent location and lovely marina to enjoy with great facilities. Will definitely be returning again very soon. Very highly recommended."
Sunseeker Renagade 60ft in Weymouth. Perfect to explore the Jurassic Coast.
One bed apartment next to Chesil Beach Dorset
King sized bed, light airy bedroom.
One bed apartment next to Chesil Beach Dorset
10.0 out of 10, Exceptional, (2)
"The apartment was very clean and modern. It was great there is a washing machine which helped immensely. The beds are very comfortable. The only downside is unloading the car as you can’t park right outside but other than that it’s perfect. I would recommend. Thanks Helen for a great stay."
One bed apartment next to Chesil Beach Dorset
Beautiful, family friendly Cottage with sea views of Chesil Beach
Room
Beautiful, family friendly Cottage with sea views of Chesil Beach
9.6 out of 10, Exceptional, (14)
"Had a lovely time good central location. Nice place to stay better than a B&B"
Beautiful, family friendly Cottage with sea views of Chesil Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Recent reviews of Portland hotels
Expedia verified reviews

Bankes Arms Hotel

Bankes Arms Hotel

5/5 Excellent
Recommend
"Perfect location, good hotel with wonderful staff. Clean, comfortable rooms. Breakfast was superb 5⭐️"
A verified traveler stayed at Bankes Arms Hotel
Posted 2 days ago
Bankes Arms Hotel