Title: Holiday Rentals Caroline County from £121: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk [Caroline County Hotels](https://expedia.co.uk/Destinations-In-Caroline-County.d553248635976434148.Hotel-Destinations)[Caroline County Car Hire](https://expedia.co.uk/Destinations-In-Caroline-County.d553248635976434148.Car-Hire-Destinations)[Caroline County Holidays](https://expedia.co.uk/Caroline-County.d553248635976434148.Holidays-City-Breaks) ![Aerial view of the Choptank River in Maryland, with calm waters and vibrant greenery](https://images.trvl-media.com/place/553248635976434148/1612c71d-0db1-48cc-9500-863759de3a04.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Holiday Rentals in Caroline County - ![](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 ## Caroline County Accommodation: Most Popular Cities to Stay ![](https://mediaim.expedia.com/destination/1/e656c6eefce865189ec0da2e321c8605.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Preston [](https://expedia.co.uk/Preston-Holiday-Rentals.d3000440824.Travel-Guide-HolidayRentals) ## Our top choices for Caroline County holiday rentals ![Property grounds](https://images.trvl-media.com/lodging/72000000/71760000/71756700/71756692/a1d87464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71760000/71756700/71756692/f9a95f78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71760000/71756700/71756692/1e473e42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71760000/71756700/71756692/7fda792d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Turnbridge Manor [](https://www.expedia.co.uk/Denton-Hotels-Turnbridge-Manor.h71756692.Hotel-Information) Denton 9.8/10 Exceptional (12) "Really nice place and you can walk to everything.Will stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Glenn S. £454 includes taxes & fees 6 Jan - 7 Jan 2026 [](https://www.expedia.co.uk/Denton-Hotels-Turnbridge-Manor.h71756692.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w1024h677x0y0-664bab42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w509h683x257y0-37962ab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w584h683x220y0-d805a755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/102000000/102000000/101992200/101992106/w451h683x287y0-42a2db1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Guest Suite for up to 2 in a Victorian on the Chester River [](https://www.expedia.co.uk/Millington-Hotels-Guest-Suite-For-Up-To-2-In-A-Victorian-On-The-Chester-River.h101992106.Hotel-Information) Millington 9.6/10 Exceptional (19) "So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia C. £96 includes taxes & fees 1 Jan - 2 Jan 2026 [](https://www.expedia.co.uk/Millington-Hotels-Guest-Suite-For-Up-To-2-In-A-Victorian-On-The-Chester-River.h101992106.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/04bd524d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/92366292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/c04c0cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/a4be0d3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### First Floor Studio Apartment in Historic Chestertown [](https://www.expedia.co.uk/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information) Chestertown 9.6/10 Exceptional (108) "Amazing and neat and very private " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexander M. £121 includes taxes & fees 29 Dec - 30 Dec [](https://www.expedia.co.uk/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/107000000/106750000/106747700/106747609/5d73c26c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/107000000/106750000/106747700/106747609/e6213ea7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106750000/106747700/106747609/9efcf95e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106750000/106747700/106747609/1d7053f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge [](https://www.expedia.co.uk/Cambridge-Hotels-The-Drinking-Gourd-Stunning-Penthouse-In-Historic-Downtown-Cambridge.h106747609.Hotel-Information) Downtown Cambridge 9.8/10 Exceptional (11) "This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lauren V. £267 includes taxes & fees 12 Jan - 13 Jan 2026 [](https://www.expedia.co.uk/Cambridge-Hotels-The-Drinking-Gourd-Stunning-Penthouse-In-Historic-Downtown-Cambridge.h106747609.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/cf034cb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, cookware/dishes/utensils](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/a9ce192e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/86c67d62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101540000/101539300/101539294/7a387636.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amazing Modern house with a full kitchen and parking [](https://www.expedia.co.uk/Smyrna-Hotels-Amazing-Modern-House-With-A-Full-Kitchen-And-Parking.h101539294.Hotel-Information) Smyrna 9.8/10 Exceptional (8) "The house is a beautiful place to stay. The location was ideal for going to attractions and stores. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laurie S. £269 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Smyrna-Hotels-Amazing-Modern-House-With-A-Full-Kitchen-And-Parking.h101539294.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/120000000/119080000/119071400/119071307/4d8cbe20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119080000/119071400/119071307/5db1e307.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/120000000/119080000/119071400/119071307/694f52a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119080000/119071400/119071307/a373d2a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### JVA LUXURY HOUSING [](https://www.expedia.co.uk/Smyrna-Hotels-JVA-LUXURY-HOUSING.h119071307.Hotel-Information) Smyrna 10/10 Exceptional (1) "The house was clean and wonderful. I highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daryl C. £443 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Smyrna-Hotels-JVA-LUXURY-HOUSING.h119071307.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/106000000/105950000/105946100/105946058/65fc84d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/106000000/105950000/105946100/105946058/167fd0dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/106000000/105950000/105946100/105946058/ee3b6008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105950000/105946100/105946058/faf796a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland [](https://www.expedia.co.uk/Cambridge-Hotels-Conductors-Rest-Beautiful-2-Bedroom-Loft-In-Historic-Cambridge.h105946058.Hotel-Information) Downtown Cambridge 10/10 Exceptional (10) "Just a beautiful place. I would stay here again. Everything was walking distance. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sylvie G. £272 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Cambridge-Hotels-Conductors-Rest-Beautiful-2-Bedroom-Loft-In-Historic-Cambridge.h105946058.Hotel-Information) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/102000000/101540000/101532700/101532690/30af39b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/102000000/101540000/101532700/101532690/7223890a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/102000000/101540000/101532700/101532690/acf170e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/102000000/101540000/101532700/101532690/26dc0ecd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf! [](https://www.expedia.co.uk/Frederica-Hotels-Totally-Remodeled-Cozy-Apartment-25-Miles-To-Delaware-Turf.h101532690.Hotel-Information) Frederica 10/10 Exceptional (17) "Great place to stay, very clean and spacious. About 20 minutes from the Dover NASCAR race which was perfect. I would absolutely recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric F. £151 includes taxes & fees 28 Dec - 29 Dec [](https://www.expedia.co.uk/Frederica-Hotels-Totally-Remodeled-Cozy-Apartment-25-Miles-To-Delaware-Turf.h101532690.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112760000/112759100/112759073/cb8b4409.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/113000000/112760000/112759100/112759073/5697af89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112760000/112759100/112759073/146a30dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/113000000/112760000/112759100/112759073/60a789b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Poe Themed Home Close to Beaches and DE Turf [](https://www.expedia.co.uk/Milford-Hotels-Poe-Themed-Home-Close-To-Beaches-And-DE-Turf.h112759073.Hotel-Information) Milford 9.6/10 Exceptional (5) "Comfortable beds, meticulous details of EA Poe throughout, walking distance to adorable Dolce’ for coffee and pastries, and lovely Milford charm are a few of the outstanding qualities of this home away from home. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda I. £210 includes taxes & fees 7 Jan - 8 Jan 2026 [](https://www.expedia.co.uk/Milford-Hotels-Poe-Themed-Home-Close-To-Beaches-And-DE-Turf.h112759073.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/120000000/119340000/119331500/119331473/61e8c463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119340000/119331500/119331473/4b162175.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/120000000/119340000/119331500/119331473/a4a8578b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119340000/119331500/119331473/868b127d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Station House East: Upscale Loft in the Historic District Cambridge, MD [](https://www.expedia.co.uk/Cambridge-Hotels-Station-House-East-Upscale-Loft-In-The-Historic-District-Cambridge.h119331473.Hotel-Information) Downtown Cambridge 10/10 Exceptional (7) £198 includes taxes & fees 11 Jan - 12 Jan 2026 [](https://www.expedia.co.uk/Cambridge-Hotels-Station-House-East-Upscale-Loft-In-The-Historic-District-Cambridge.h119331473.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/100000000/99690000/99684200/99684191/51cd6ca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99690000/99684200/99684191/1792ceb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99690000/99684200/99684191/b3c1fc85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/100000000/99690000/99684200/99684191/c7785aa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina [](https://www.expedia.co.uk/Cambridge-Hotels-Cozy-2-Bedroom.h99684191.Hotel-Information) Cambridge 9.6/10 Exceptional (20) "In town for a family wedding. This worked out perfectly. Would stay there again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara V. £267 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Cambridge-Hotels-Cozy-2-Bedroom.h99684191.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/82000000/81260000/81259300/81259255/b3fc30c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/82000000/81260000/81259300/81259255/e94dd853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/82000000/81260000/81259300/81259255/c03397f0.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/82000000/81260000/81259300/81259255/0251fd8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sailwinds Loft at Cambridge Creek [](https://www.expedia.co.uk/Cambridge-Hotels-Sailwinds-Loft-At-Cambridge-Creek.h81259255.Hotel-Information) Cambridge 10/10 Exceptional (24) "What a great place to relax after exploring and enjoying the area. Definitely will visit again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris S. £193 includes taxes & fees 3 Jan - 4 Jan 2026 [](https://www.expedia.co.uk/Cambridge-Hotels-Sailwinds-Loft-At-Cambridge-Creek.h81259255.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/97000000/96120000/96117900/96117871/e7ff4058.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Games room](https://images.trvl-media.com/lodging/97000000/96120000/96117900/96117871/c3524691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96120000/96117900/96117871/5ae97cc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, ping pong](https://images.trvl-media.com/lodging/97000000/96120000/96117900/96117871/4d65add6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Waterfront Retreat in Cambridge! [](https://www.expedia.co.uk/Cambridge-Hotels-Beautiful-Waterfront-Retreat-In-Cambridge.h96117871.Hotel-Information) Cambridge 10/10 Exceptional (50) "Beautiful place! Loved all the activities, will return in the future! Our family and friends had a blast! Thank you so much!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen L. £282 includes taxes & fees 6 Jan - 7 Jan 2026 [](https://www.expedia.co.uk/Cambridge-Hotels-Beautiful-Waterfront-Retreat-In-Cambridge.h96117871.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/104000000/103590000/103584900/103584811/e8133ca5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103590000/103584900/103584811/70d83c34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103590000/103584900/103584811/dea9ce41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103590000/103584900/103584811/aece230b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland [](https://www.expedia.co.uk/Cambridge-Hotels-Upscale-Condo-In-Historic-Downtown-Cambridge.h103584811.Hotel-Information) Downtown Cambridge 8.4/10 Very good (6) "Perfectly located in town and well appointed, comfortable quarters. We would stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard D. £225 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Cambridge-Hotels-Upscale-Condo-In-Historic-Downtown-Cambridge.h103584811.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83070000/83066200/83066154/3f6b4c84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83070000/83066200/83066154/fcc4baa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83070000/83066200/83066154/c86d900d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83070000/83066200/83066154/0b964f44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### WATERFRONT!! \*\*HOT TUB\*\* 3 bedroom Oasis on 2+ acres - Sleeps 8 [](https://www.expedia.co.uk/Cambridge-Hotels-WATERFRONT-3-Bed-Oasis-On-2-Acres-Sleeps-8.h83066154.Hotel-Information) Cambridge 10/10 Exceptional (14) "Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jill C. £400 includes taxes & fees 2 Jan - 3 Jan 2026 [](https://www.expedia.co.uk/Cambridge-Hotels-WATERFRONT-3-Bed-Oasis-On-2-Acres-Sleeps-8.h83066154.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/64000000/63650000/63641700/63641659/7fd63e9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/64000000/63650000/63641700/63641659/2b76d904.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63650000/63641700/63641659/053c923e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63650000/63641700/63641659/c5ddefd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Breezes - quiet waterfront retreat [](https://www.expedia.co.uk/Cambridge-Hotels-Sunset-Breezes-Quiet-Waterfront-Retreat.h63641659.Hotel-Information) Dorchester County 10/10 Exceptional (41) "Good time with my friends " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Oleg L. £259 includes taxes & fees 30 Dec - 31 Dec [](https://www.expedia.co.uk/Cambridge-Hotels-Sunset-Breezes-Quiet-Waterfront-Retreat.h63641659.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/737f2153.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) "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. £315 includes taxes & fees 29 Dec - 30 Dec [](https://www.expedia.co.uk/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/101000000/100290000/100285400/100285322/w449h683x288y0-03622767.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100290000/100285400/100285322/w1024h675x0y4-d4e73536.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100290000/100285400/100285322/w1024h675x0y4-d63d4766.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, table football](https://images.trvl-media.com/lodging/101000000/100290000/100285400/100285322/w1024h676x0y4-1256b46e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 5 Bedroom w/Pool, Patio and Theater [](https://www.expedia.co.uk/Magnolia-Hotels-Spacious-5-Bedroom-WPatio.h100285322.Hotel-Information) Magnolia 9.8/10 Exceptional (7) "Great house for a large family " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie £534 includes taxes & fees 30 Dec - 31 Dec [](https://www.expedia.co.uk/Magnolia-Hotels-Spacious-5-Bedroom-WPatio.h100285322.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/ee0975c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/25541a3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/3c8498e2.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/103000000/102640000/102631200/102631144/259066d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### HGTV quality, private guest suite, country getaway with hot tub & fire pit [](https://www.expedia.co.uk/Centreville-Hotels-Private.h102631144.Hotel-Information) Centreville 10/10 Exceptional (8) "Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Renee P. £337 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Centreville-Hotels-Private.h102631144.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76790000/76790000/76789996/3748d5d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76790000/76790000/76789996/e9b94408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/77000000/76790000/76790000/76789996/6b6f5c14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/77000000/76790000/76790000/76789996/8ff2c2b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Unit in Milford, Delaware -Close to DE Turf [](https://www.expedia.co.uk/Milford-Hotels-Cozy-Unit-In-Milford.h76789996.Hotel-Information) Milford 10/10 Exceptional (2) "Perfect place for my son and I that had a lacrosse tourney that was only 8 minutes away at the Delaware turf fields Cat was awesome and replied very fast and was super accommodating!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shaine L. £171 includes taxes & fees 30 Dec - 31 Dec [](https://www.expedia.co.uk/Milford-Hotels-Cozy-Unit-In-Milford.h76789996.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=2026-01-09&endDate=2026-01-10®ionId=553248635976434148&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=Caroline+County%2C+Maryland%2C+United+States+of+America®ionId=553248635976434148&latLong=38.884558%2C-75.827156&adults=2&startDate=2026-03-26&d1=2026-03-26&endDate=2026-03-29&d2=2026-03-29&lodging=APARTMENT) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Caroline+County%2C+Maryland%2C+United+States+of+America®ionId=553248635976434148&latLong=38.884558%2C-75.827156&adults=2&startDate=2026-03-26&d1=2026-03-26&endDate=2026-03-29&d2=2026-03-29&lodging=CONDO) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Caroline+County%2C+Maryland%2C+United+States+of+America®ionId=553248635976434148&latLong=38.884558%2C-75.827156&adults=2&startDate=2026-03-26&d1=2026-03-26&endDate=2026-03-29&d2=2026-03-29&lodging=VACATION_HOME) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=Caroline+County%2C+Maryland%2C+United+States+of+America®ionId=553248635976434148&latLong=38.884558%2C-75.827156&adults=2&startDate=2026-03-26&d1=2026-03-26&endDate=2026-03-29&d2=2026-03-29&lodging=VILLA) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Caroline+County%2C+Maryland%2C+United+States+of+America®ionId=553248635976434148&latLong=38.884558%2C-75.827156&adults=2&startDate=2026-03-26&d1=2026-03-26&endDate=2026-03-29&d2=2026-03-29&lodging=COTTAGE) Cabins [](https://www.expedia.co.uk/Hotel-Search?destination=Caroline+County%2C+Maryland%2C+United+States+of+America®ionId=553248635976434148&latLong=38.884558%2C-75.827156&adults=2&startDate=2026-03-26&d1=2026-03-26&endDate=2026-03-29&d2=2026-03-29&lodging=CABIN) ![](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%2FDestinations-In-Caroline-County.d553248635976434148.Holiday-Rental-Destinations)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Caroline-County.d553248635976434148.Holiday-Rental-Destinations) ## Top Caroline County Hotel Reviews ![Bally's Dover Casino Resort](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572988/b37bb6df_y.jpg) ### Bally's Dover Casino Resort 10/10 Excellent "Satisfied customer." [](https://expedia.co.uk/Dover-Hotels-Dover-Downs-Hotel-Casino.h1572988.Hotel-Information) ![Microtel Inn & Suites by Wyndham Dover](https://images.trvl-media.com/lodging/2000000/1510000/1509700/1509695/b1bab4b1_y.jpg) ### Microtel Inn & Suites by Wyndham Dover 10/10 Excellent "The room was neat, clean and well-stocked with the essentials. The front desk staff was friendly and professional. We stay here every year!the location is quiet and convenient. " [](https://expedia.co.uk/Dover-Hotels-Microtel-Inn-Suites-By-Wyndham-Dover.h1509695.Hotel-Information) ![Days Inn & Suites by Wyndham Seaford](https://images.trvl-media.com/lodging/2000000/1620000/1610400/1610385/71c71954_y.jpg) ### Days Inn & Suites by Wyndham Seaford 10/10 Excellent "Easy check in, spotless room quiet comfortable a great place to rest for the evening. Multiple food options near by. Very nice staff!" [](https://expedia.co.uk/Seaford-Hotels-Days-Inn-Suites-By-Wyndham-Seaford.h1610385.Hotel-Information) ![Hampton Inn Salisbury](https://images.trvl-media.com/lodging/1000000/290000/282000/281943/633fd984_y.jpg) ### Hampton Inn Salisbury 10/10 Excellent "To be completely honest, every single staff member was very kind and accommodating to my family. This was something that really made the chaos of my day feel so easy. I was able to get a wonderful nights rest. The hotel is absolutely clean, there’s coffee all day long, wonderful spaces throughout for guests to enjoy intimate conversations, a great workout facility, a wonderful indoor pool. I have zero complaints about this place. I will come back here every single time without fail" [](https://expedia.co.uk/Salisbury-Hotels-Hampton-Inn-Salisbury.h281943.Hotel-Information) ![Hyatt Place Kent Narrows & Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86_y.jpg) ### Hyatt Place Kent Narrows & Marina 10/10 Excellent "Clean, friendly and " [](https://expedia.co.uk/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![Springhill Suites By Marriott Frederica](https://images.trvl-media.com/lodging/96000000/95070000/95062700/95062671/9f69013a_y.jpg) ### Springhill Suites By Marriott Frederica 10/10 Excellent "Very clean and comfy " [](https://expedia.co.uk/Frederica-Hotels-Springhill-Suites-By-Marriott-Frederica.h95062671.Hotel-Information) ![Hilton Garden Inn Kent Island Marina](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/367a733a_y.jpg) ### Hilton Garden Inn Kent Island Marina 10/10 Excellent "Clean and friendly staff" [](https://expedia.co.uk/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) ![Best Western Kent Narrows Inn](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3968d160_y.jpg) ### Best Western Kent Narrows Inn 10/10 Excellent "Nice place " [](https://expedia.co.uk/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![Microtel Inn & Suites By Wyndham Georgetown Delaware Beaches](https://images.trvl-media.com/lodging/9000000/8750000/8740800/8740727/1c6278af_y.jpg) ### Microtel Inn & Suites By Wyndham Georgetown Delaware Beaches 10/10 Excellent "Room was nice, front desk very friendly and helpful. Breakfast was full every day." [](https://expedia.co.uk/Rehoboth-Beach-Hotels-Microtel-Inn-Suites-By-Wyndham-Georgetown-Delaware-Beaches.h8740727.Hotel-Information) ## Find out more about Caroline County **Everything you need to know about** **Caroline County** **holiday rentals** Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Caroline County holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Caroline County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. **Caroline County holiday rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Caroline County. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in . Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Caroline County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Caroline County holiday rentals we have selected for you start as low as £121 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Caroline County rentals** At Expedia, we put the best Caroline County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. To find some top Caroline County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Caroline County holiday. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Caroline County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. ## Explore a world of travel with Expedia - Popular Caroline County Cities - [Preston Holiday Rentals ](https://expedia.co.uk/Preston-Holiday-Rentals.d3000440824.Travel-Guide-HolidayRentals)