[See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Fair Winds at Chesil Beach Vacation home in Portland ![Beach nearby](https://images.trvl-media.com/lodging/103000000/102090000/102083000/102082945/w1609h1071x6y4-8632e901.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Private kitchen](https://images.trvl-media.com/lodging/103000000/102090000/102083000/102082945/63c57085.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Living area](https://images.trvl-media.com/lodging/103000000/102090000/102083000/102082945/aa8bdb8b.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Private kitchen](https://images.trvl-media.com/lodging/103000000/102090000/102083000/102082945/991715f4.jpg?impolicy=resizecrop&rw=297&ra=fit) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102090000/102083000/102082945/ce944860.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location Nestled near the ocean and Portland Marina, Fair Winds offers a peaceful retreat with sea views just minutes from Portland Castle Beach and Chesil Beach. Stroll along the coast or relax in this modern home, where free parking is provided. 9.8 Exceptional ### Entire home 2 bedrooms1 bathroomSleeps 4 ## Popular amenities - Washer - Free WiFi - Ocean view ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### Fair Winds at Chesil Beach Fair Winds offers a getaway just a stone's throw from the ocean and Portland Marina. Wake up to sea views and stroll 2 minutes to Portland Castle Beach, or 5 minutes to the renowned Chesil Beach. The interior of our home boasts a contemporary style, blending modern amenities with a cosy, welcoming atmosphere. Free parking is provided. Whether you're seeking a peaceful retreat or an adventure by the sea, Fair Winds is the ideal base for exploring the wonders of Dorset's stunning coastline. ## Property amenities ### Beach - Beach nearby ### Internet - Available in the house: Free WiFi ### Bedrooms - 2 bedrooms - Bedsheets provided ### Bathroom - 1 bathroom - Soap - Toilet paper - Towels provided ### Laundry - Laundry facilities - Washing machine ### Comfort - Heating ### Pets - No pets allowed ### Suitability/Accessibility - Smoking not allowed ### Safety features - Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector) - Smoke detector not reported (host has not indicated whether there is a smoke detector on the property) ## Similar properties ![Marina](https://images.trvl-media.com/lodging/104000000/103030000/103021500/103021437/fca7d34e.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Cove Cottage - Brewers Quay Harbour Weymouth - Kitchen - Washer - Dryer - Pet-friendly 10 Exceptional 1 review [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-28&endDate=2025-10-29&selected=103021437&PinnedHotelID=103021437&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach](https://images.trvl-media.com/lodging/115000000/114470000/114466900/114466873/0a197687.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 3 bedroom accommodation in Portland Portland - Kitchen - Washer - Pet-friendly - Free WiFi [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-28&endDate=2025-10-29&selected=114466873&PinnedHotelID=114466873&HadPinnedHotel=true®ionId=-1&adults=2) ![On the beach](https://images.trvl-media.com/lodging/115000000/114380000/114370500/114370404/5388887e.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Host & Stay | The Aquamarine Weymouth Beach Weymouth - Ocean view - Kitchen - Washer - Dryer [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-28&endDate=2025-10-29&selected=114370404&PinnedHotelID=114370404&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach nearby](https://images.trvl-media.com/lodging/34000000/33660000/33650500/33650414/10637d8c.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Close to Weymouth Harbour and Hope Square. 10 minutes walk to Weymouth beach. Weymouth - Kitchen - Washer - Dryer - Free WiFi 9.8 Exceptional 50 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-28&endDate=2025-10-29&selected=33650414&PinnedHotelID=33650414&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach nearby](https://images.trvl-media.com/lodging/34000000/33590000/33580200/33580124/8e446ef2.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Luxury mobile home with spectacular sea views. Weymouth - Ocean view - Pool - Kitchen - Washer 9.8 Exceptional 119 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-28&endDate=2025-10-29&selected=33580124&PinnedHotelID=33580124&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach nearby](https://images.trvl-media.com/lodging/31000000/30080000/30077400/30077346/19bbb671.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Beautiful, family friendly Cottage with sea views of Chesil Beach Fortuneswell - Ocean view - Kitchen - Washer - Free WiFi 9.4 Exceptional 23 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-28&endDate=2025-10-29&selected=30077346&PinnedHotelID=30077346&HadPinnedHotel=true®ionId=-1&adults=2) ## Policies ### Check-in Check-in time starts at 2:00 PM Minimum check-in age: 18 ### Check-out Check-out before 10:00 AM ### Special check-in instructions You will receive an email from the host with check-in and check-out instructions ### Pets Pets not allowed ### Children and extra beds Children are welcome ### Events No events allowed ### Smoking Smoking is not permitted ## Important information ### You need to know Extra-person charges may apply and vary depending on property policy Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed Onsite parties or group events are strictly prohibited Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip Host has not indicated whether there is a smoke detector on the property This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation ## About the area Located in Portland, this vacation home is near the beach. The area's natural beauty can be seen at Weymouth Beach and Chesil Beach. Bennetts Water Gardens and Pirate Adventure Mini Golf are also worth visiting. [Visit our Portland travel guide](https://www.expedia.ca/Portland.dx182615) [View more Vacation homes in Portland](https://www.expedia.ca/Portland-Private-Vacation-Homes.d182615-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C50.56651%2C-2.44860&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=OUGdRqxQNeELmokdRSzqnJoYWxQ=) Portland, dorset ### What's nearby - Portland Castle - 3 min walk - 0.3 km - Portland Harbour - 8 min walk - 0.7 km - Weymouth Harbour - 9 min drive - 6.8 km - Weymouth Beach - 9 min drive - 7.1 km - Chesil Beach - 34 min drive - 23.5 km ### Getting around - Weymouth Station - 14 min drive - Bournemouth (BOH-Bournemouth Intl.) - 73 min drive ### Restaurants - ‪Beehive - ‬3 min walk - ‪The Wyke Smugglers - ‬5 min drive - ‪Crab House Cafe - ‬4 min drive - ‪The Little Ship - ‬7 min walk - ‪Old Castle Hotel - ‬7 min drive ## Frequently asked questions ### Is Fair Winds at Chesil Beach pet-friendly? > No, pets are not allowed at this property. ### What time is check-in at Fair Winds at Chesil Beach? > Check-in begins at 2:00 PM. ### What time is check-out at Fair Winds at Chesil Beach? > Check-out is at 10:00 AM. ### Where is Fair Winds at Chesil Beach located? > Situated near the beach, this vacation home is within a 5-minute walk of Portland Castle, Weymouth Bay, and Dorset and East Devon Coast. Portland Beach and Portland Harbour are also within 10 minutes. ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. 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