Title: Holiday Rentals Caroline County from £124: 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) ![](https://mediaim.expedia.com/destination/1/49aeb39d1297aa325883028ae03bfba2.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) ## Top Holiday Rentals in Caroline County ![Marina](https://images.trvl-media.com/lodging/95000000/94680000/94672700/94672644/w1799h1199x1y1-608c1c0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/95000000/94680000/94672700/94672644/w1799h1198x1y1-8dbb76d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/95000000/94680000/94672700/94672644/w1799h1199x1y1-8b0bbec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/95000000/94680000/94672700/94672644/w1799h1199x1y1-bea6e8a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cass-N-Reel Luxury Houseboat Grasonville 10/10 Exceptional (45) "If you’re looking for a great view sitting on the water, with a modern look, convenient to everything, you need to stay on the Cass-and-Reel Luxury Houseboat!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen B. [](https://www.expedia.co.uk/Grasonville-Hotels-Cass-N-Reel-Luxury-Houseboat.h94672644.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/93000000/92010000/92008700/92008639/0809820d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/93000000/92010000/92008700/92008639/0310a691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92010000/92008700/92008639/8a60f7ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/93000000/92010000/92008700/92008639/1a21e043.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly) Cambridge 10/10 Exceptional (14) "Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dara M. [](https://www.expedia.co.uk/Cambridge-Hotels-Cozy-Cottage-With-Private-Dock-Chesapeake-Bay-Cambridge.h92008639.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33506200/33506110/1dc9ddc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33510000/33506200/33506110/b73afede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/34000000/33510000/33506200/33506110/d6f3062d.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/34000000/33510000/33506200/33506110/c5d1df22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family and Pet-Friendly, Waterfront with Pier Cambridge 10/10 Exceptional (262) "Our stay was great and Rob and Clarissa were very welcoming!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Allison L. [](https://www.expedia.co.uk/Cambridge-Hotels-Family-And-Pet-Friendly.h33506110.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/c5bdec51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/afb23ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/10a98dfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/0d1878e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels! Saint Michaels 9.6/10 Exceptional (122) "The house and location was perfect for a girls weekend with my mom and 2 daughters! The 1/2 bathrooms in each bedroom were nice to have upstairs!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly L. [](https://www.expedia.co.uk/St-Michaels-Hotels-John-Bruff-Waterview-Cottage-On-Harbor-And-On-Park-In-Town-St-Michaels.h32562385.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67330000/67326000/67325935/ac0c320c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/68000000/67330000/67326000/67325935/611460b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67330000/67326000/67325935/9b1c6ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67330000/67326000/67325935/69201425.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Captain's Quarters Frederica 9.8/10 Exceptional (101) "This house is a really nice hidden gem in a hidden gem town. The house is equipped with all that you need to have a great time on vacation. Bikes, beach chairs, corn hole, kids sand toys, well stocked kitchen. This place is a gem!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Walter H. [](https://www.expedia.co.uk/Dover-Hotels-Captains-Quarters.h67325935.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/90000000/89180000/89179200/89179147/d6394886.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89180000/89179200/89179147/c261da12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89180000/89179200/89179147/c299076c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89180000/89179200/89179147/c8bcbd97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock Cambridge 9.8/10 Exceptional (7) "The property was perfect for our family get together. We had a baby, toddler, preschooler, elementary and teens, moms, dads and grandparents. There was a place for everyone. Having a pack n’ play available would have been nice, but we procured one elsewhere. The property was large and felt very private, but Cambridge was just a quick drive." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacqueline M. [](https://www.expedia.co.uk/Cambridge-Hotels-NEW-Gorgeous-Waterfront-Estate-In-Cambridge-Md.h89179147.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/24000000/23560000/23560000/23559917/df5a2ad2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/24000000/23560000/23560000/23559917/795447d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/24000000/23560000/23560000/23559917/569495f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/24000000/23560000/23560000/23559917/4cadae45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy cottage on the Miller farm. Milford 10/10 Exceptional (237) "Awesome place. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael D. [](https://www.expedia.co.uk/Milford-Hotels-Cozy-Cottage-On-The-Miller-Farm.h23559917.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34350000/34340300/34340251/f36704f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/35000000/34350000/34340300/34340251/39c9a1b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34350000/34340300/34340251/3c996507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/35000000/34350000/34340300/34340251/6e046b2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28 Cambridge 10/10 Exceptional (79) "Good stay overall" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bill C. [](https://www.expedia.co.uk/Cambridge-Hotels-Year-Round-Waterfront-Estate-Family-Reunions-Retreats-Sleeps-28.h34340251.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/34000000/33550000/33549200/33549150/w1624h1084x0y2-ec718b23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun-loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33550000/33549200/33549150/580dc6a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33550000/33549200/33549150/afb6f363.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33550000/33549200/33549150/f9c952d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock Woolford 9.8/10 Exceptional (74) "As beautiful as the photos appear, they do NOT do this place justice! Just a beautiful place, incredibly peaceful, well-appointed and equipped for families, groups, or any type of rental. Loved our time here!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael E. [](https://www.expedia.co.uk/Woolford-Hotels-Newer-Luxury-Waterfront-Beach.h33549150.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/b94b1ba5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/fb9a7f0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/38fa4ea8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/7c62e911.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife St. Michaels 9.8/10 Exceptional (44) "This cottage is adorable. Great amenities and great location. We thoroughly enjoyed our time in St Michael’s." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Audra B. [](https://www.expedia.co.uk/St-Michaels-Hotels-Carpenter-Alley-Newly-Renovated-Cottage-In-Center-Of-Historic-St-Michaels.h48378570.Hotel-Information) ![Smart TV, books, printers](https://images.trvl-media.com/lodging/96000000/95860000/95854100/95854099/60be688f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95860000/95854100/95854099/04b58eb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95860000/95854100/95854099/c09f4ad6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/96000000/95860000/95854100/95854099/32d5fc72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks Woolford 9.6/10 Exceptional (21) "The house was very nice, the host was very responsive! The outside was nice, only down side lots of mosquitos but that’s expected. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth M. [](https://www.expedia.co.uk/Woolford-Hotels-The-Blue-Heron-Spacious-Waterfront-Eastern-Shore-Getaway-With-Kayaks.h95854099.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34330000/34323900/34323855/179041b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34330000/34323900/34323855/691f4295.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34330000/34323900/34323855/3245ad2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34330000/34323900/34323855/w1919h1439x0y0-289d79c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town St Michaels 9.6/10 Exceptional (146) "Perfect place to stay for a cousins reunion, Central location to all the shops and restaurants." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amh S. [](https://www.expedia.co.uk/St-Michaels-Hotels-Premier-St-Michaels-Cottage-T-Blades-House-Walk-To-Everything-In-Town.h34323855.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/33000000/32600000/32590200/32590170/7dc8015a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32600000/32590200/32590170/831e4185.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/33000000/32600000/32590200/32590170/22b0e30e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/33000000/32600000/32590200/32590170/w1919h1440x0y0-69f18a52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels St Michaels 9.6/10 Exceptional (125) "Beautiful house Great location. We really enjoyed our first visit to St. Michaels!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JIM S. [](https://www.expedia.co.uk/St-Michaels-Hotels-Location.h32590170.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/83000000/82950000/82943900/82943888/7d8af0d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/83000000/82950000/82943900/82943888/d807abc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82950000/82943900/82943888/cbbbb52d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, offices](https://images.trvl-media.com/lodging/83000000/82950000/82943900/82943888/c0d26cf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Flat in the Heart of St. Michaels – Walk Everywhere Saint Michaels 10/10 Exceptional (53) "Beautiful, clean and well appointed in the perfect spot in downtown Saint Michael’s. Highly recommended!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey G. [](https://www.expedia.co.uk/St-Michaels-Hotels-The-Heart-Of-St-Michaels-Awaits.h82943888.Hotel-Information) ![Private beach](https://images.trvl-media.com/lodging/93000000/92610000/92607300/92607228/caba515d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/93000000/92610000/92607300/92607228/275e7818.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92610000/92607300/92607228/f992df15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92610000/92607300/92607228/c387167f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access Sherwood 10/10 Exceptional (19) "Gorgeous views and location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan D. [](https://www.expedia.co.uk/Sherwood-Hotels-Time-Stands-Still.h92607228.Hotel-Information) ![Sun-loungers, beach towels](https://images.trvl-media.com/lodging/65000000/64570000/64567900/64567851/a8374ca7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/65000000/64570000/64567900/64567851/f3ee6fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/65000000/64570000/64567900/64567851/0e893115.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/65000000/64570000/64567900/64567851/a7c6934a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND Sherwood 10/10 Exceptional (37) "We went to Sherwood to celebrate a family event. The house was perfect - lots of room for everyone. Check-in was simple, house was in excellent condition and the owners made every effort to accommodate our needs (some extra equipment for little kids). We enjoyed the pool and the beautiful setting. Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James S. [](https://www.expedia.co.uk/Sherwood-Hotels-Heated-Pool-CHESAPEAKE-MANSION-12.h64567851.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33710000/33706000/33705957/9bbf68fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33710000/33706000/33705957/780a1972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games, DVD player, video library](https://images.trvl-media.com/lodging/34000000/33710000/33706000/33705957/fced1e30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, travel cot, free WiFi](https://images.trvl-media.com/lodging/34000000/33710000/33706000/33705957/w800h599x0y1-c77560c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW Cambridge 9.8/10 Exceptional (133) "Beautiful property with gorgeous view. The owner was helpful and accommodating. Everything was clean and the amenities were superb. An evening of kayaking on the water was amazing. Great location for the half Ironman as well! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn R. [](https://www.expedia.co.uk/Cambridge-Hotels-Waterfront-Family-Retreat-With-Gorgeous-Views-And-A-Large-Deepwater-Dock-5-MLW.h33705957.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) ![1 bedroom, in-room safe, free WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/44ce5b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### First Floor Studio Apartment in Historic Chestertown Chestertown 9.6/10 Exceptional (105) "Wonderful stay in a beautiful location convenient to everything. Host was outstanding." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Randy B. £124 includes taxes & fees 19 Nov - 20 Nov [](https://www.expedia.co.uk/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/115000000/114390000/114380200/114380126/fbbf0dca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/115000000/114390000/114380200/114380126/f45a57f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/115000000/114390000/114380200/114380126/e0fcab5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114390000/114380200/114380126/c5d66854.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### RELAX- Eastern Shore Creek Home - 6 Guests Grasonville 10/10 Exceptional (5) "We had a real enjoyable and comfortable stay in this beautiful home. The hosts were very responsive and the amenities were much appreciated. The home made this special trip even more memorable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sherry N. [](https://www.expedia.co.uk/Grasonville-Hotels-RELAX-Eastern-Shore-Creek-Home.h114380126.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/58000000/57570000/57568000/57567941/92da0bac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/58000000/57570000/57568000/57567941/b96757cd.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/58000000/57570000/57568000/57567941/87aff82c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/58000000/57570000/57568000/57567941/9b02a761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### St. Michaels Waterfront Home New comb 9.8/10 Exceptional (31) "What a great place to stay!! Close to town and very well equipped. We’ll be back!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Craig W. [](https://www.expedia.co.uk/Easton-Hotels-St-Michaels-Waterfront-Home.h57567941.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=2025-11-25&endDate=2025-11-26®ionId=553248635976434148&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](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](//images.trvl-media.com/lodging/2000000/1580000/1573000/1572988/b37bb6df_y.jpg) ### Bally's Dover Casino Resort 10/10 Excellent "Clean room, great view of the track, excellent friendly staff in the hotel and casino. " [](https://expedia.co.uk/Dover-Hotels-Dover-Downs-Hotel-Casino.h1572988.Hotel-Information) ![Days Inn by Wyndham Salisbury](//images.trvl-media.com/lodging/1000000/20000/16300/16257/3d6af3ed_y.jpg) ### Days Inn by Wyndham Salisbury 10/10 Excellent "Great over night stay" [](https://expedia.co.uk/Salisbury-Hotels-Days-Inn-By-Wyndham-Salisbury.h16257.Hotel-Information) ![Holiday Inn Express Hotel & Suites Dover by IHG](//images.trvl-media.com/lodging/1000000/600000/597800/597727/6d0ff772_y.jpg) ### Holiday Inn Express Hotel & Suites Dover by IHG 10/10 Excellent "This is my go to hotel when in Delaware . I love the friendliness of the staff. " [](https://expedia.co.uk/Dover-Hotels-Holiday-Inn-Express-Hotel-Suites-Dover.h597727.Hotel-Information) ![Hyatt Place Kent Narrows & Marina](//images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86_y.jpg) ### Hyatt Place Kent Narrows & Marina 10/10 Excellent "The employees were friendly and helpful. Rooms were clean and the anenties were in good working order" [](https://expedia.co.uk/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![Red Roof Inn & Suites Dover Downtown](//images.trvl-media.com/lodging/1000000/890000/888000/887960/473c4e31_y.jpg) ### Red Roof Inn & Suites Dover Downtown 10/10 Excellent "Great" [](https://expedia.co.uk/Dover-Hotels-Red-Roof-Inn-Suites-Dover-Downtown.h887960.Hotel-Information) ![Comfort Inn & Suites](//images.trvl-media.com/lodging/2000000/1840000/1831100/1831095/c1d84f60_y.jpg) ### Comfort Inn & Suites 10/10 Excellent "Quiet, clean, and convenient. " [](https://expedia.co.uk/Dover-Hotels-Comfort-Inn-Suites.h1831095.Hotel-Information) ![Microtel Inn & Suites By Wyndham Georgetown Delaware Beaches](//images.trvl-media.com/lodging/9000000/8750000/8740800/8740727/1c6278af_y.jpg) ### Microtel Inn & Suites By Wyndham Georgetown Delaware Beaches 10/10 Excellent "Stay was great. Linda did a great job checking us in. She accommodated us by switching out our room. It was very clean. Breakfast was great!!" [](https://expedia.co.uk/Rehoboth-Beach-Hotels-Microtel-Inn-Suites-By-Wyndham-Georgetown-Delaware-Beaches.h8740727.Hotel-Information) ![Microtel Inn & Suites by Wyndham Milford](//images.trvl-media.com/lodging/65000000/64920000/64916800/64916777/3f703075_y.jpg) ### Microtel Inn & Suites by Wyndham Milford 10/10 Excellent "Spotless room and great staff. We enjoyed sitting in the lobby/breakfast area with 24 hour coffee and tea. This has become our go to location ib Delaware." [](https://expedia.co.uk/Dover-Hotels-Microtel-Inn-Suites-By-Wyndham-Milford.h64916777.Hotel-Information) ![Microtel Inn & Suites by Wyndham Dover](//images.trvl-media.com/lodging/2000000/1510000/1509700/1509695/b1bab4b1_y.jpg) ### Microtel Inn & Suites by Wyndham Dover 10/10 Excellent "The room and staff were great!" [](https://expedia.co.uk/Dover-Hotels-Microtel-Inn-Suites-By-Wyndham-Dover.h1509695.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 £124 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)