Title: Fair Winds at Chesil Beach - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=182615&destination=Portland%2C+England%2C+United+Kingdom&selected=102082945&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Fair Winds at Chesil Beach ## Photo gallery for Fair Winds at Chesil Beach ![Living area - Fair Winds at Chesil Beach (Portland)](https://images.trvl-media.com/lodging/103000000/102090000/102083000/102082945/eef2cb13.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Beach nearby - Fair Winds at Chesil Beach (Portland)](https://images.trvl-media.com/lodging/103000000/102090000/102083000/102082945/w1609h1071x6y4-8632e901.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Living area - Fair Winds at Chesil Beach (Portland)](https://images.trvl-media.com/lodging/103000000/102090000/102083000/102082945/aa8bdb8b.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Dining - Fair Winds at Chesil Beach (Portland)](https://images.trvl-media.com/lodging/103000000/102090000/102083000/102082945/90651f94.jpg?impolicy=resizecrop&rw=297&ra=fit) ![2 bedrooms, free WiFi, bed sheets - Fair Winds at Chesil Beach (Portland)](https://images.trvl-media.com/lodging/103000000/102090000/102083000/102082945/159d4418.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies 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. ## Reviews 9.8 Exceptional ### Entire home 2 bedrooms1 bathroomSleeps 4 ## Popular amenities - Ocean view - Washer - Free WiFi ## 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 ![Cottage | Interior](https://images.trvl-media.com/lodging/60000000/59650000/59649000/59648969/bd002153.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Panoramic View Portland - Pool - Kitchen - Washer - Parking included [](https://www.expedia.ca/Hotel-Search?startDate=2026-04-01&endDate=2026-04-02&selected=59648969&PinnedHotelID=59648969&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/92000000/91630000/91621500/91621464/12b7a0e3.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Bear's Apartment Portland - Pool - Kitchen - Parking included - Free WiFi CA $861 CA $1,033 total includes taxes & fees Mar 21 - Mar 22 [](https://www.expedia.ca/Hotel-Search?startDate=2026-03-21&endDate=2026-03-22&selected=91621464&PinnedHotelID=91621464&HadPinnedHotel=true®ionId=-1&adults=2) [Compare similar properties](/Hotel-Search?startDate=2026-04-01&endDate=2026-04-02&selected=102082945&PinnedHotelID=102082945&HadPinnedHotel=true®ionId=-1&adults=2&comparePropertyIds=102082945,59648969,91621464) ## 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 Information provided by the property may be translated using automated translation tools ### 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 Durdle Door. Osprey Leisure Centre and Bennetts Water Gardens 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 - ![Durdle Door, Wareham, United Kingdom](https://images.trvl-media.com/place/182682/c5ed7add-c104-42ce-8724-4a699e31d6ea.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Weymouth Bay 3 min walk \- 0.3 km - ![Jurassic Coast](https://images.trvl-media.com/place/553248635998143517/df9d8755-7b81-4a85-a556-f42f0cd6c73d.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Dorset and East Devon Coast 3 min walk \- 0.3 km - Portland Castle 3 min walk \- 0.3 km - Weymouth and Portland National Sailing Academy 8 min walk \- 0.7 km - Portland Harbour 8 min walk \- 0.7 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 - Sticks And Bones 9 min drive - The Cove House Inn 10 min walk ## Frequently asked questions ### Is Fair Winds at Chesil Beach pet-friendly? ### What time is check-in at Fair Winds at Chesil Beach? ### What time is check-out at Fair Winds at Chesil Beach? ### Where is Fair Winds at Chesil Beach located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Fair Winds at Chesil Beach Reviews ## Reviews 9.8 ### Exceptional ### Expedia's Latest Trends ### Hotels > - [Seacote Hotel](https://www.expedia.ca/St-Bees-Hotels-Seacote-Hotel.h15731415.Hotel-Information) > - [Parkview Apartments](https://www.expedia.ca/High-Wycombe-Hotels-Parkview-Apartments.h32463857.Hotel-Information) > - [Private detached cottage to rent on Chesil Beach](https://www.expedia.ca/Weymouth-Hotels-Vrbo-Property.h39977662.Hotel-Information) > - [Low Wood Bay Resort & Spa](https://www.expedia.ca/Windermere-Hotels-Low-Wood-Bay.h5243.Hotel-Information) > - [Village Hotel Warrington](https://www.expedia.ca/Warrington-Hotels-Village-Hotel-Warrington.h8696.Hotel-Information) > - [Harbour Hotel St Ives](https://www.expedia.ca/St-Ives-Hotels-St-Ives-Harbour-Hotel.h175599.Hotel-Information) > - [The Lantana](https://www.expedia.ca/Weymouth-Hotels-The-Lantana.h32462453.Hotel-Information) > - [No Man's Fort](https://www.expedia.ca/Portsmouth-Hotels-No-Mans-Fort.h11536410.Hotel-Information) > - [Acqua Beach](https://www.expedia.ca/Weymouth-Hotels-Acqua-Beach.h4189361.Hotel-Information) > - [Broadlands Guest House](https://www.expedia.ca/Windermere-Hotels-Broadlands-Guest-House.h18420266.Hotel-Information) > - [The White Hart Royal Hotel, Moreton-in-Marsh](https://www.expedia.ca/Moreton-In-Marsh-Hotels-White-Hart-Royal-Hotel.h3848404.Hotel-Information) > - [Sandford House Hotel by Wetherspoon ](https://www.expedia.ca/Huntingdon-Hotels-Sandford-House-Hotel-By-Wetherspoon.h49136820.Hotel-Information) > - [Harbour View](https://www.expedia.ca/Brixham-Hotels-Harbour-View.h23925647.Hotel-Information) > - [The Pearl Hotel](https://www.expedia.ca/Peterborough-Hotels-The-Pearl-Hotel.h6335144.Hotel-Information) > - [Marina Court Hotel](https://www.expedia.ca/Weymouth-Hotels-Marina-Court-Hotel.h24454235.Hotel-Information) > - [Harris House](https://www.expedia.ca/Doncaster-Hotels-Harris-House.h24719309.Hotel-Information) > - [The Ocean Guest House](https://www.expedia.ca/Weymouth-Hotels-The-Ocean-Guest-House.h78249454.Hotel-Information) > - [The Manor House](https://www.expedia.ca/Scarborough-Hotels-The-Manor-House.h44509462.Hotel-Information) > - [Best Western Weymouth Hotel Rembrandt](https://www.expedia.ca/Weymouth-Hotels-Best-Western-Weymouth-Hotel-Rembrandt.h4102869.Hotel-Information) > - [YotelAIR London Gatwick ](https://www.expedia.ca/Gatwick-Hotels-Yotel-Air-London-Gatwick.h18969729.Hotel-Information) > - [Pennyhill Park Hotel And Spa](https://www.expedia.ca/Bagshot-Hotels-Pennyhill-Park-Hotel-And-Spa.h517256.Hotel-Information) > - [The George](https://www.expedia.ca/Cheltenham-Hotels-The-George-Hotel.h45140643.Hotel-Information) > - [Tregarland Farm B&B](https://www.expedia.ca/Looe-Hotels-Tregarland-Farm-BB.h40111725.Hotel-Information) > - [Doubletree by Hilton Hotel Woking](https://www.expedia.ca/Woking-Hotels-Doubletree-By-Hilton-Hotel-Woking.h786850.Hotel-Information) > - [Ranscombe House](https://www.expedia.ca/Brixham-Hotels-Ranscombe-House.h33222653.Hotel-Information) > - [The Kings Head Hotel](https://www.expedia.ca/Dereham-Hotels-The-Kings-Head-Hotel.h6983061.Hotel-Information) > - [Middle Flass Lodge](https://www.expedia.ca/Clitheroe-Hotels-Middle-Flass-Lodge.h4531075.Hotel-Information) > - [Tides Cottage](https://www.expedia.ca/Pevensey-Hotels-Tides-Cottage.h42241061.Hotel-Information) > - [Delta Hotels by Marriott Peterborough](https://www.expedia.ca/Peterborough-Hotels-Peterborough-Marriott-Hotel.h691233.Hotel-Information)