Title: TOP Hotels with Entertainment in Portland for 2026 | Expedia.co.uk [Portland Travel Guide](https://expedia.co.uk/Portland.dx182615)[Hotels in Portland](https://expedia.co.uk/Portland-Hotels.d182615.Travel-Guide-Hotels)[Holiday Rentals in Portland](https://expedia.co.uk/Portland-Holiday-Rentals.d182615.Travel-Guide-HolidayRentals)[Things to do in Portland](https://expedia.co.uk/Things-To-Do-In-Portland.d182615.Travel-Guide-Activities)[Portland Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Portland.d182615.Car-Hire-Guide)[Portland Holidays](https://expedia.co.uk/Portland.d182615.Holidays-City-Breaks) ![Adobe](https://images.trvl-media.com/place/182615/0db1baf5-d984-433d-99e7-8908d576f968.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/182615/0db1baf5-d984-433d-99e7-8908d576f968.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Portland Hotels with Entertainment Tonight [17 Feb - 18 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=182615&startDate=2026-02-17&endDate=2026-02-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [18 Feb - 19 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=182615&startDate=2026-02-18&endDate=2026-02-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [20 Feb - 22 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=182615&startDate=2026-02-20&endDate=2026-02-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [27 Feb - 1 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=182615&startDate=2026-02-27&endDate=2026-03-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Portland hotels with entertainment ![Standard Apartment, Ensuite (Shared Terrace) | Floor plan](https://images.trvl-media.com/lodging/4000000/3500000/3496600/3496530/5e080d2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Suite, Private Bathroom (portland1)](https://images.trvl-media.com/lodging/4000000/3500000/3496600/3496530/c4b3f8fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Apartment, Ensuite (Shared Terrace) | Dining](https://images.trvl-media.com/lodging/4000000/3500000/3496600/3496530/81c221ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Apartment, Ensuite (Shared Terrace) | Shared kitchen](https://images.trvl-media.com/lodging/4000000/3500000/3496600/3496530/e8426fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wilton Guest House [](https://www.expedia.co.uk/Weymouth-Hotels-The-Wilton-Guest-House.h3496530.Hotel-Information) Weymouth 7.8/10 Good (176 reviews) "Guest house was in walking distance of everything and parking just across the road would stay there again " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Sandra £66 includes taxes & fees 19 Feb - 20 Feb [](https://www.expedia.co.uk/Weymouth-Hotels-The-Wilton-Guest-House.h3496530.Hotel-Information) ![32-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/1000000/900000/892300/892279/d1198738.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room | Premium bedding, pillow-top beds, individually decorated](https://images.trvl-media.com/lodging/1000000/900000/892300/892279/b5a24f0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/900000/892300/892279/c4eaac26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/900000/892300/892279/918a2a5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleeping Bear Hotel Dorchester [](https://www.expedia.co.uk/Dorchester-Hotels-Sleeping-Bear-Hotel-Dorchester.h892279.Hotel-Information) Dorchester 8.8/10 Excellent (568 reviews) "Very pleasant stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Russell £53 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Dorchester-Hotels-Sleeping-Bear-Hotel-Dorchester.h892279.Hotel-Information) ![Bed sheets](https://images.trvl-media.com/lodging/5000000/4060000/4052300/4052265/593d9aef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bed sheets](https://images.trvl-media.com/lodging/5000000/4060000/4052300/4052265/24b3b41c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/5000000/4060000/4052300/4052265/a9da7a3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dock](https://images.trvl-media.com/lodging/5000000/4060000/4052300/4052265/db75b005.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aaran Guesthouse [](https://www.expedia.co.uk/Weymouth-Hotels-Aaran-Guesthouse.h4052265.Hotel-Information) Weymouth 9.4/10 Exceptional (224 reviews) "Room was clean and comfortable Excellent location Very good breakfast Lovely host" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Alison £113 includes taxes & fees 23 Feb - 24 Feb [](https://www.expedia.co.uk/Weymouth-Hotels-Aaran-Guesthouse.h4052265.Hotel-Information) ![Lounge](https://images.trvl-media.com/lodging/103000000/102660000/102656100/102656084/9de02004.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/103000000/102660000/102656100/102656084/99a8b088.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/103000000/102660000/102656100/102656084/6a31842e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/103000000/102660000/102656100/102656084/f52fe3dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jurassic Bay Holidays [](https://www.expedia.co.uk/Weymouth-Hotels-Jurassic-Bay-Holidays.h102656084.Hotel-Information) Weymouth 8.8/10 Excellent (5 reviews) "Was great property for family to all stay in one room. Had everything we needed . Would stay again Thank you " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Rachel £90 includes taxes & fees 18 Feb - 19 Feb [](https://www.expedia.co.uk/Weymouth-Hotels-Jurassic-Bay-Holidays.h102656084.Hotel-Information) ![Cottage | Interior](https://images.trvl-media.com/lodging/45000000/44460000/44459200/44459143/fb5dc36e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | Interior](https://images.trvl-media.com/lodging/45000000/44460000/44459200/44459143/cd2a5754.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | Property grounds](https://images.trvl-media.com/lodging/45000000/44460000/44459200/44459143/1256a00c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | Interior](https://images.trvl-media.com/lodging/45000000/44460000/44459200/44459143/387554cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterson [](https://www.expedia.co.uk/Weymouth-Hotels-Waterson.h44459143.Hotel-Information) Weymouth 8.0/10 Very good (1 review) "lovely location , inside house a little tired " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Nigel £906 includes taxes & fees 23 Feb - 24 Feb [](https://www.expedia.co.uk/Weymouth-Hotels-Waterson.h44459143.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/75000000/74900000/74899100/74899098/191ca34c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/75000000/74900000/74899100/74899098/bc7a7d85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, Ensuite, Sea View | 1 bedroom](https://images.trvl-media.com/lodging/75000000/74900000/74899100/74899098/07ef060e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room, Ensuite, Sea View | 1 bedroom](https://images.trvl-media.com/lodging/75000000/74900000/74899100/74899098/f5baecf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chapter 1 Hotels [](https://www.expedia.co.uk/Weymouth-Hotels-Chapter-1-Hotels.h74899098.Hotel-Information) Weymouth 10/10 Exceptional (100 reviews) "Very clean and comfortable…enjoyed the breakfast " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Simon £125 includes taxes & fees 18 Feb - 19 Feb [](https://www.expedia.co.uk/Weymouth-Hotels-Chapter-1-Hotels.h74899098.Hotel-Information) ![Room](https://images.trvl-media.com/lodging/7000000/6350000/6342800/6342769/w500h371x0y0-3cfc08a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/7000000/6350000/6342800/6342769/49085975.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/7000000/6350000/6342800/6342769/be7ecb6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/7000000/6350000/6342800/6342769/c7446d30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Clifton Hotel [](https://www.expedia.co.uk/Weymouth-Hotels-The-Clifton-Hotel.h6342769.Hotel-Information) Weymouth 8.8/10 Excellent (296 reviews) "Great stay" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Kerry Ann £98 includes taxes & fees 24 Feb - 25 Feb [](https://www.expedia.co.uk/Weymouth-Hotels-The-Clifton-Hotel.h6342769.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/45000000/44460000/44458200/44458160/32ed8002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | Pool | Outdoor pool](https://images.trvl-media.com/lodging/45000000/44460000/44458200/44458160/d7f4671d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | Living room](https://images.trvl-media.com/lodging/45000000/44460000/44458200/44458160/fb682f0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | Dining](https://images.trvl-media.com/lodging/45000000/44460000/44458200/44458160/ddf963ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Churn House [](https://www.expedia.co.uk/Dorchester-Hotels-Churn-House.h44458160.Hotel-Information) Dorchester £791 includes taxes & fees 23 Feb - 24 Feb [](https://www.expedia.co.uk/Dorchester-Hotels-Churn-House.h44458160.Hotel-Information) ![Cottage | Private kitchen | Dishwasher, cookware/dishes/utensils](https://images.trvl-media.com/lodging/45000000/44460000/44456400/44456347/28731599.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/45000000/44460000/44456400/44456347/2f10b0de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | Dining](https://images.trvl-media.com/lodging/45000000/44460000/44456400/44456347/92a6a082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | 8 bedrooms, individually decorated, individually furnished, free WiFi](https://images.trvl-media.com/lodging/45000000/44460000/44456400/44456347/020f7c2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Manor Farm Barn [](https://www.expedia.co.uk/Dorchester-Hotels-Manor-Farm-Barn.h44456347.Hotel-Information) Dorchester £2,122 includes taxes & fees 12 Mar - 13 Mar [](https://www.expedia.co.uk/Dorchester-Hotels-Manor-Farm-Barn.h44456347.Hotel-Information) ![Cottage | Interior](https://images.trvl-media.com/lodging/45000000/44460000/44456600/44456501/w2500h1874x0y0-c1726028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | Interior](https://images.trvl-media.com/lodging/45000000/44460000/44456600/44456501/5b518463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | Interior](https://images.trvl-media.com/lodging/45000000/44460000/44456600/44456501/ef68ada6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | Interior](https://images.trvl-media.com/lodging/45000000/44460000/44456600/44456501/a5d73f00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbourside House [](https://www.expedia.co.uk/Weymouth-Hotels-Harbourside-House.h44456501.Hotel-Information) Weymouth £1,364 includes taxes & fees 20 Feb - 21 Feb [](https://www.expedia.co.uk/Weymouth-Hotels-Harbourside-House.h44456501.Hotel-Information) 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. [View all properties](https://expedia.co.uk/Hotel-Search?startDate=2026-03-03&endDate=2026-03-04®ionId=182615&adults=2&nearby_group=entertainment&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=AFFINITY_SPRING_PROMO_182615) ## Top Portland Hotel Reviews ![Sleeping Bear Hotel Dorchester](https://images.trvl-media.com/lodging/1000000/900000/892300/892279/e83c8493_y.jpg) ### Sleeping Bear Hotel Dorchester 10/10 Excellent "Clean, warm room. Felt happy and safe as a lone-female traveller. Close to plenty of choice of food outlets." [](https://expedia.co.uk/Dorchester-Hotels-Sleeping-Bear-Hotel-Dorchester.h892279.Hotel-Information) ![The Lugger Inn](https://images.trvl-media.com/lodging/5000000/4590000/4589200/4589174/253e8ac0_y.jpg) ### The Lugger Inn 10/10 Excellent "Awesome place people are friendly hotel amazing we are definitely coming back here the owner well he couldnt of done enough for us thank you " [](https://expedia.co.uk/Weymouth-Hotels-The-Lugger-Inn.h4589174.Hotel-Information) ## Explore a world of travel with Expedia - Accommodation - [Business Hotels in Dorset ](https://www.expedia.co.uk/Destinations-In-Dorset-Business-Hotel.0-0-d6046198-tBusinessHotel.Hotel-Filter-Destinations) - [Casino Hotels in Dorset ](https://www.expedia.co.uk/Destinations-In-Dorset-Casino-Hotel.0-0-d6046198-tCasinoHotel.Hotel-Filter-Destinations) - [Golf Hotels in Dorset ](https://www.expedia.co.uk/Destinations-In-Dorset-Golf-Hotels.0-0-d6046198-tGolfHotels.Hotel-Filter-Destinations) - [Green Hotels in Dorset ](https://www.expedia.co.uk/Destinations-In-Dorset-Green-Sustainable.0-0-d6046198-tGreenSustainable.Hotel-Filter-Destinations) - 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