Title: Chester Holiday Homes from £109: Search Holiday Homes in Chester | Expedia.co.uk [Hotels in Chester](https://expedia.co.uk/Chester-Hotels.d3000440455.Travel-Guide-Hotels)[Holiday Rentals in Chester](https://expedia.co.uk/Chester-Holiday-Rentals.d3000440455.Travel-Guide-HolidayRentals)[Chester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chester.d3000440455.Car-Hire-Guide)[Chester Holidays](https://expedia.co.uk/Chester.d3000440455.Holidays-City-Breaks) ![](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Patricia Knorr ![](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2.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 prices for these dates In two weeks [24 Apr - 26 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=3000440455&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [5 Jun - 7 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=3000440455&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [3 Jul - 5 Jul](https://www.expedia.co.uk/Hotel-Search?regionId=3000440455&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [31 Jul - 2 Aug](https://www.expedia.co.uk/Hotel-Search?regionId=3000440455&startDate=2026-07-31&endDate=2026-08-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester holiday homes ![Exterior detail](https://images.trvl-media.com/lodging/129000000/128420000/128417500/128417470/55152f23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/129000000/128420000/128417500/128417470/3d3727e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/129000000/128420000/128417500/128417470/6a4e6884.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/129000000/128420000/128417500/128417470/073cfcb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Annapolis Gem- Tranquil 4 BR Murray Hill Victorian [](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Gem-Tranquil-4-BR-Murray-Hill-Victorian.h128417470.Hotel-Information) Historic District £384 includes taxes & fees 20 Apr - 21 Apr [](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Gem-Tranquil-4-BR-Murray-Hill-Victorian.h128417470.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/a71c8e39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/w1024h678x0y5-f3e384c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/7d796cd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/c53ddff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Coastal/Country Home w/3 Acres & Sauna! [](https://www.expedia.co.uk/Stevensville-Hotels-Charming-CoastalCountry-Home-W3-Acres-Sauna.h84063895.Hotel-Information) Stevensville 9.6/10 Exceptional (35 reviews) "Great stay, would do it again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon D. £183 includes taxes & fees 12 Apr - 13 Apr [](https://www.expedia.co.uk/Stevensville-Hotels-Charming-CoastalCountry-Home-W3-Acres-Sauna.h84063895.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/57f188cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/12356e9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/99582f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/80cf0fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax on Kent Island in a 4 Bedroom Home w/Waterview! [](https://www.expedia.co.uk/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information) Stevensville 9.8/10 Exceptional (43 reviews) "We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Supriya V. £180 includes taxes & fees 12 Apr - 13 Apr [](https://www.expedia.co.uk/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/2a64ee56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table football](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/44a64359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/23f1d475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/30ebd57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 2 bedroom duplex located conveniently near Route 50 East and West. [](https://www.expedia.co.uk/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.Hotel-Information) Grasonville 9.6/10 Exceptional (12 reviews) "Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joe C. £312 includes taxes & fees 9 Apr - 10 Apr [](https://www.expedia.co.uk/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/a2c7c68e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/4cfce214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/8ae0a25a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/21befbf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayside Cottage steps from Rock Hall Harbor [](https://www.expedia.co.uk/Rock-Hall-Hotels-Bayside-Cottage-Steps-From-Rock-Hall-Harbor.h83921931.Hotel-Information) Rock Hall 10/10 Exceptional (2 reviews) "Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dorothy R. £264 includes taxes & fees 20 Apr - 21 Apr [](https://www.expedia.co.uk/Rock-Hall-Hotels-Bayside-Cottage-Steps-From-Rock-Hall-Harbor.h83921931.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/e5c30638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/a5c24734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/86c425c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/3a482076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large 2 bedroom house with private parking in a nice neighborhood [](https://www.expedia.co.uk/Arnold-Hotels-Large-2-Bedroom-House-Private-Parking-Nice-Neighborhood.h89057630.Hotel-Information) Arnold 9.4/10 Exceptional (38 reviews) "Super clean place, great communication from the host, and home is exactly as described and shown in pictures. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Traci L. £244 includes taxes & fees 9 Apr - 10 Apr [](https://www.expedia.co.uk/Arnold-Hotels-Large-2-Bedroom-House-Private-Parking-Nice-Neighborhood.h89057630.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/3f3bd4d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/bf60932b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/28005d62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/42bbbfcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk to Beach! King Bed & Free Beach Passes [](https://www.expedia.co.uk/North-Beach-Hotels-Plant-Filled-Oasis-Near-Beach-Town-With-Passes-Tips.h69541327.Hotel-Information) North Beach 10/10 Exceptional (19 reviews) "Delightful one-night stay! Place was clean, quiet, convenient and very comfortable. Especially grateful that our beloved dog was welcomed" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elaine D. £257 includes taxes & fees 12 Apr - 13 Apr [](https://www.expedia.co.uk/North-Beach-Hotels-Plant-Filled-Oasis-Near-Beach-Town-With-Passes-Tips.h69541327.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/0cad4612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/3334515c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/0cab7732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101090000/101083600/101083507/f79dd58b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bay Ridge unit by Downtown Annapolis and Quiet Waters Park [](https://www.expedia.co.uk/Annapolis-Hotels-Bay-Ridge-Unit-By-Downtown-Annapolis-And-Quiet-Waters-Park.h101083507.Hotel-Information) Annapolis 8.8/10 Excellent (3 reviews) "The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William £358 includes taxes & fees 9 Apr - 10 Apr [](https://www.expedia.co.uk/Annapolis-Hotels-Bay-Ridge-Unit-By-Downtown-Annapolis-And-Quiet-Waters-Park.h101083507.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/93000000/92090000/92080200/92080111/w4000h1746x0y0-fc1adaf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92090000/92080200/92080111/68ce83bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92090000/92080200/92080111/w4000h1729x0y0-ae4201db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92090000/92080200/92080111/2b0352ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### BAYSIDE BUNGALOW [](https://www.expedia.co.uk/Rock-Hall-Hotels-BAYSIDE-BUNGALOW.h92080111.Hotel-Information) Rock Hall 10/10 Exceptional (52 reviews) "Very quaint and quiet place to stay. Very relaxing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roger £207 includes taxes & fees 4 May - 5 May [](https://www.expedia.co.uk/Rock-Hall-Hotels-BAYSIDE-BUNGALOW.h92080111.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/dc0187f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/3f9288e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/6b287c9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/ea596829.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Annapolis Home | Fenced Yard | Pool Table | 10 Guests [](https://www.expedia.co.uk/Annapolis-Hotels-Neptune-By-The-Water.h101897342.Hotel-Information) Cape Saint Claire 9.8/10 Exceptional (11 reviews) "Enjoyed our stay- thank you!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) KateriK £417 includes taxes & fees 15 Apr - 16 Apr [](https://www.expedia.co.uk/Annapolis-Hotels-Neptune-By-The-Water.h101897342.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/110000000/109470000/109465100/109465066/197cec39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109470000/109465100/109465066/61b9de4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109470000/109465100/109465066/b3eeb69f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/110000000/109470000/109465100/109465066/d339d550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded Tiny Pool House -Private Pool -Self Check in [](https://www.expedia.co.uk/Glen-Burnie-Hotels-CLEAN.h109465066.Hotel-Information) Glen Burnie 8.6/10 Excellent (10 reviews) "Jordan was a great host and communicated in a timely and professional manner. Outdoor space and pool were lovely for the hot sunny weekend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ellie F. £109 includes taxes & fees 9 Apr - 10 Apr [](https://www.expedia.co.uk/Glen-Burnie-Hotels-CLEAN.h109465066.Hotel-Information) ![Beach nearby, sun-loungers, beach towels](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/35e98514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/5c5b72be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/8a80c02f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/92000000/91040000/91033700/91033683/825e8c03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach [](https://www.expedia.co.uk/Annapolis-Hotels-Charming-Cottage-With-Hot-Tub-1-Block-From-The-Bay.h91033683.Hotel-Information) Arundel on the Bay 9.6/10 Exceptional (13 reviews) "Great communication with the host, easy check in.. nice property. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Henry P. £460 includes taxes & fees 20 Apr - 21 Apr [](https://www.expedia.co.uk/Annapolis-Hotels-Charming-Cottage-With-Hot-Tub-1-Block-From-The-Bay.h91033683.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/c81ba3f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/85376bca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/0348d35e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/4ec9c7d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Pet-Friendly Stay - Near Bay & Beaches. [](https://www.expedia.co.uk/Annapolis-Hotels-Cozy-Retreat-Near-The-Bay.h113272210.Hotel-Information) Annapolis 10/10 Exceptional (7 reviews) "Very clean and very convenient location for our trip. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Greg S. £395 includes taxes & fees 4 May - 5 May [](https://www.expedia.co.uk/Annapolis-Hotels-Cozy-Retreat-Near-The-Bay.h113272210.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/d0edf916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun-loungers, beach towels](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/c0808af9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/b40492dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/e5b3706d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants [](https://www.expedia.co.uk/North-Beach-Hotels-Huge-Beach-Bungalow-WYard.h83966408.Hotel-Information) North Beach 10/10 Exceptional (32 reviews) "Perfect place to spend quality time with our three adult children and their significant others. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Malarkey F. £361 includes taxes & fees 4 May - 5 May [](https://www.expedia.co.uk/North-Beach-Hotels-Huge-Beach-Bungalow-WYard.h83966408.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/9d27d09a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/8f010e7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/c889c2aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/125000000/124830000/124829800/124829757/dd15abfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cute, Cozy 2-bedroom house in near Annapolis with water access [](https://www.expedia.co.uk/Crownsville-Hotels-Cute.h124829757.Hotel-Information) Herald Harbor 9.6/10 Exceptional (4 reviews) "Just as advertised no issues. Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dan O. £176 includes taxes & fees 21 Apr - 22 Apr [](https://www.expedia.co.uk/Crownsville-Hotels-Cute.h124829757.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305193/a5cfb38f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305193/b36dd134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Renovated Bungalow | Walk to Beach | Dog-Friendly [](https://www.expedia.co.uk/Edgewater-Hotels-London-Towne-Bungalow-WLoft-Walk-To-The-Beach.h96305193.Hotel-Information) Edgewater 9.2/10 Wonderful (5 reviews) "Very cute house. It was exactly what I was looking for. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Collin G. £350 includes taxes & fees 12 Apr - 13 Apr [](https://www.expedia.co.uk/Edgewater-Hotels-London-Towne-Bungalow-WLoft-Walk-To-The-Beach.h96305193.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/d00ee2e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/48c7542a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/8156a7b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/100000000/99480000/99470800/99470706/9df6bc62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Annapolis Retreat - 7 mins from downtown Annapolis! [](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Retreat-7-Mins-From-Downtown-Annapolis.h99470706.Hotel-Information) Hillsmere 10/10 Exceptional (6 reviews) "Great house in cute neighborhood. Thanks for a very comfortable stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul C. £397 includes taxes & fees 21 Apr - 22 Apr [](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Retreat-7-Mins-From-Downtown-Annapolis.h99470706.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/841d93b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/b6d125f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/e8979b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100210000/100202700/100202663/b3be55ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cute bungalow blocks to Stadium [](https://www.expedia.co.uk/Annapolis-Hotels-Cute-Bungalow-Blocks-To-Stadium.h100202663.Hotel-Information) Admiral Heights 9.8/10 Exceptional (8 reviews) "Great property. Third time staying at property while visiting Annapolis. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Holly W. £386 includes taxes & fees 20 Apr - 21 Apr [](https://www.expedia.co.uk/Annapolis-Hotels-Cute-Bungalow-Blocks-To-Stadium.h100202663.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/fc34c762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/7e2b4765.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/081c863e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/4de85be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2br home w/ parking in downtown Annapolis [](https://www.expedia.co.uk/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information) Historic District 10/10 Exceptional (75 reviews) "Welcoming host, great location and easy parking " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris B. £266 includes taxes & fees 5 May - 6 May [](https://www.expedia.co.uk/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/101000000/100560000/100556100/100556061/83e5c5cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100560000/100556100/100556061/f220c1f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100560000/100556100/100556061/6352c6da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100560000/100556100/100556061/1cd38316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Annapolis Home | 2 Blocks to Main St [](https://www.expedia.co.uk/Annapolis-Hotels-Fisher-House-Downtown-Annapolis.h100556061.Hotel-Information) Historic District 10/10 Exceptional (16 reviews) "Great house and location. Great communication. We had a great time there!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara S. £491 includes taxes & fees 13 Apr - 14 Apr [](https://www.expedia.co.uk/Annapolis-Hotels-Fisher-House-Downtown-Annapolis.h100556061.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=2026-04-22&endDate=2026-04-23®ionId=3000440455&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find holiday rentals that suit your style Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-07-07&d1=2026-07-07&endDate=2026-07-10&d2=2026-07-10&lodging=APARTMENT) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-07-07&d1=2026-07-07&endDate=2026-07-10&d2=2026-07-10&lodging=VACATION_HOME) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-07-07&d1=2026-07-07&endDate=2026-07-10&d2=2026-07-10&lodging=CONDO) Houseboats [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-07-07&d1=2026-07-07&endDate=2026-07-10&d2=2026-07-10&lodging=HOUSE_BOAT) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America®ionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-07-07&d1=2026-07-07&endDate=2026-07-10&d2=2026-07-10&lodging=COTTAGE) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChester-Private-Holiday-Homes.d3000440455-aaPrivateHolidayHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Private-Holiday-Homes.d3000440455-aaPrivateHolidayHomes.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![Hampton Inn & Suites Annapolis](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/ff58e28e_y.jpg) ### Hampton Inn & Suites Annapolis 6/10 Okay "Dirty mirrors, broken irons, super sensitive smoke detectors (went off twice because of iron) couch bed super uncomfortable " [](https://expedia.co.uk/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.Hotel-Information) ![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/0f404f98_y.jpg) ### Crowne Plaza Annapolis by IHG 6/10 Okay "Would have been nice to know when booking (or in advance) that the jacuzzi was out of service. I was looking forward to that. For the name sake, there was nothing special about this hotel. Would have been nice to have an included breakfast for the price." [](https://expedia.co.uk/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/eac8c079_y.jpg) ### Sonesta ES Suites Annapolis 10/10 Excellent "Super spacious and clean. Would stay again" [](https://expedia.co.uk/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![Country Inn & Suites by Radisson, Annapolis, MD](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/65a79802_y.jpg) ### Country Inn & Suites by Radisson, Annapolis, MD 8/10 Good "I enjoyed my stay. The staff was friendly and the room was clean. The breakfast provided had a great variety. The only draw back was the pool hours. I didn’t get to enjoy it as the two days I was there it was closed one day and the other day I was out exploring the area and DC so by time I came back it was already closed. " [](https://expedia.co.uk/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![The Westin Annapolis](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/73550aaf_y.jpg) ### The Westin Annapolis 10/10 Excellent "Beautiful hotel. Great location. Friendly staff. " [](https://expedia.co.uk/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) ![Best Western Kent Narrows Inn](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3217cd56_y.jpg) ### Best Western Kent Narrows Inn 10/10 Excellent "Yes very good" [](https://expedia.co.uk/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![SpringHill Suites by Marriott Annapolis](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/80b99d82_y.jpg) ### SpringHill Suites by Marriott Annapolis 4/10 Poor "The room did not have a fresh smell, toilet clogged. No new sheets or cleaned room 2 nd day" [](https://expedia.co.uk/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information) ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "Fantastic accessibility to all shops" [](https://expedia.co.uk/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Good location, fair price" [](https://expedia.co.uk/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ## Find out more about Chester ## Chester Holiday Homes information | Number of reviews | 337 | | ----------------- | ----------------- | | Accommodation | 659 Holiday Homes | | Lowest Price | £109 | | Highest Price | £491 | ## Explore a world of travel with Expedia - More ways to book - [Book Holiday Homes in Chester on Expedia.com ](https://www.expedia.com/Chester-Private-Vacation-Homes.d3000440455-aaPrivateVacationHomes.Travel-Guide-Accommodation)