Title: Caroline County Vacation Home Rentals from CA $495: Search Top Private Vacation Homes for Rent | Expedia.ca

[Caroline County Hotels](https://expedia.ca/Destinations-In-Caroline-County.d553248635976434148.Hotel-Destinations)[Vacation Rentals in Caroline County](https://expedia.ca/Destinations-In-Caroline-County.d553248635976434148.Vacation-Rental-Destinations)[Caroline County Car Rentals](https://expedia.ca/Destinations-In-Caroline-County.d553248635976434148.Car-Rental-Destinations)[Caroline County Vacations](https://expedia.ca/Caroline-County.d553248635976434148.Destination-Travel-Guides)

![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)

![](https://images.trvl-media.com/place/553248635976434148/1612c71d-0db1-48cc-9500-863759de3a04.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976434148&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976434148&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 three months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=553248635976434148&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976434148&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Cities in Caroline County

![Coastal tidal wetlands on a Sunny Day](https://images.trvl-media.com/place/6048051/e996e186-4e79-48c6-925b-58265ba3dd44.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Denton

[](https://expedia.ca/Denton-Private-Vacation-Homes.d6048051-aaPrivateVacationHomes.Travel-Guide-Accommodation)

![Cute, well cared for, and very uncrowded state park in Maryland. Rent a canoe and paddle up into the creeks that feed the lake for views of abundant plants and wildlife.](https://images.trvl-media.com/place/151310/7c7c13f3-3715-48f7-943a-0eb2ce0b7451.jpg?impolicy=fcrop&w=384&h=216&q=medium)

#### Ridgely

[](https://expedia.ca/Ridgely-Private-Vacation-Homes.d151310-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Our top choices for Caroline County vacation homes

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/120000000/119430000/119421100/119421004/94be7c8c.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/120000000/119430000/119421100/119421004/3d6049ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119430000/119421100/119421004/39de6af0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/120000000/119430000/119421100/119421004/c5a697bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Dover

[](https://www.expedia.ca/Dover-Hotels-Charming-3-Bedroom-Ranch-In-Delightful-Dover-With-AC.h119421004.Hotel-Information)

10/10

Exceptional

(1 review)

"Host was great"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

mark o.

[](https://www.expedia.ca/Dover-Hotels-Charming-3-Bedroom-Ranch-In-Delightful-Dover-With-AC.h119421004.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/24000000/23560000/23560000/23559917/4cadae45.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23560000/23560000/23559917/417b111c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/24000000/23560000/23560000/23559917/1fc32ebf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Milford

[](https://www.expedia.ca/Milford-Hotels-Cozy-Cottage-On-The-Miller-Farm.h23559917.Hotel-Information)

10/10

Exceptional

(242 reviews)

"Wonderfully quiet location with amazing amenities and beautiful scenery."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jason A.

[](https://www.expedia.ca/Milford-Hotels-Cozy-Cottage-On-The-Miller-Farm.h23559917.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/100000000/99690000/99684200/99684191/69bef312.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99690000/99684200/99684191/3651a7b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99690000/99684200/99684191/7cf0d433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99690000/99684200/99684191/7f132b5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cambridge

[](https://www.expedia.ca/Cambridge-Hotels-Cozy-2-Bedroom.h99684191.Hotel-Information)

9.6/10

Exceptional

(20 reviews)

"Very nice place in a great location. We would definitely stay there again "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Traci C.

CA $206

CA $495 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Cambridge-Hotels-Cozy-2-Bedroom.h99684191.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/111000000/110630000/110624500/110624456/664d3b8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110630000/110624500/110624456/c87acf22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books](https://images.trvl-media.com/lodging/111000000/110630000/110624500/110624456/ae68592d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/111000000/110630000/110624500/110624456/f3047f59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Greenwood

[](https://www.expedia.ca/Greenwood-Hotels-Backroad-Getaway-Newly-Build-3-Bedroom-Retreat-In-Greenwood-With-WiFi.h110624456.Hotel-Information)

9.8/10

Exceptional

(38 reviews)

"Great home and location for what we needed. Would stay here again.. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Matt F.

[](https://www.expedia.ca/Greenwood-Hotels-Backroad-Getaway-Newly-Build-3-Bedroom-Retreat-In-Greenwood-With-WiFi.h110624456.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)

![Exterior](https://images.trvl-media.com/lodging/90000000/89180000/89179200/89179147/5b711a62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/90000000/89180000/89179200/89179147/0d5f6e4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/90000000/89180000/89179200/89179147/1dd72939.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cambridge

[](https://www.expedia.ca/Cambridge-Hotels-NEW-Gorgeous-Waterfront-Estate-In-Cambridge-Md.h89179147.Hotel-Information)

9.8/10

Exceptional

(8 reviews)

"Great House "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Conrad L.

[](https://www.expedia.ca/Cambridge-Hotels-NEW-Gorgeous-Waterfront-Estate-In-Cambridge-Md.h89179147.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)

![Dining](https://images.trvl-media.com/lodging/96000000/95860000/95854100/95854099/32d5fc72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95860000/95854100/95854099/6522734b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95860000/95854100/95854099/714ac46f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Woolford

[](https://www.expedia.ca/Woolford-Hotels-The-Blue-Heron-Spacious-Waterfront-Eastern-Shore-Getaway-With-Kayaks.h95854099.Hotel-Information)

9.4/10

Exceptional

(25 reviews)

"House was wonderful, it had something for all ages, plenty of room for our group of 17\. We also had family that lived nearby by over for breakfast one morning and still plenty of room. Lots of utensils for all our cooking needs. House was very clean. Host was very responsive with a couple of questions we had. Everyone enjoyed their stay with many memories made."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

robert p.

[](https://www.expedia.ca/Woolford-Hotels-The-Blue-Heron-Spacious-Waterfront-Eastern-Shore-Getaway-With-Kayaks.h95854099.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/4d36e439.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)

![Exterior](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/fb9a7f0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Downtown St. Michaels

[](https://www.expedia.ca/St-Michaels-Hotels-Carpenter-Alley-Newly-Renovated-Cottage-In-Center-Of-Historic-St-Michaels.h48378570.Hotel-Information)

9.8/10

Exceptional

(49 reviews)

"Conveniently located!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer E.

[](https://www.expedia.ca/St-Michaels-Hotels-Carpenter-Alley-Newly-Renovated-Cottage-In-Center-Of-Historic-St-Michaels.h48378570.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/95000000/94340000/94339600/94339545/c21af27f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/95000000/94340000/94339600/94339545/a1341ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/95000000/94340000/94339600/94339545/8cc5d867.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/95000000/94340000/94339600/94339545/ed7a797d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Frederica

[](https://www.expedia.ca/Frederica-Hotels-Wind-Song-Getaway-On-The-Beach.h94339545.Hotel-Information)

9.8/10

Exceptional

(34 reviews)

"Location was nice, beautiful sunrises. Plenty of room, beds were super comfy and communication with owner was wondering!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lisa K.

[](https://www.expedia.ca/Frederica-Hotels-Wind-Song-Getaway-On-The-Beach.h94339545.Hotel-Information)

![](https://images.trvl-media.com/lodging/89000000/88320000/88312200/88312172/8ca2391a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/89000000/88320000/88312200/88312172/a64fd577.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/89000000/88320000/88312200/88312172/8dc1b18d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/89000000/88320000/88312200/88312172/900dee21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Centreville

[](https://www.expedia.ca/Centreville-Hotels-Waterfront-Estate-W-Private-Pier.h88312172.Hotel-Information)

9.6/10

Exceptional

(38 reviews)

"Great location and plenty of fun"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Carl S.

[](https://www.expedia.ca/Centreville-Hotels-Waterfront-Estate-W-Private-Pier.h88312172.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111880000/111870400/111870337/5058fafc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/112000000/111880000/111870400/111870337/d24bcc11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/112000000/111880000/111870400/111870337/77230418_edited_976a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111880000/111870400/111870337/d4b7a366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Frederica

[](https://www.expedia.ca/Frederica-Hotels-Charming-Bungalow-Water-Views-In-Bowers-Beach-AC-WiFi-Dover-Downs-AFB-DE-Turf.h111870337.Hotel-Information)

9.4/10

Exceptional

(3 reviews)

"Adorable cottage. Excellent location. We will definitely rent again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ed M.

[](https://www.expedia.ca/Frederica-Hotels-Charming-Bungalow-Water-Views-In-Bowers-Beach-AC-WiFi-Dover-Downs-AFB-DE-Turf.h111870337.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/120000000/119130000/119124200/119124197/3e0b227c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119130000/119124200/119124197/7e7317d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119130000/119124200/119124197/26e808a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119130000/119124200/119124197/3ecd7c34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Chestertown

[](https://www.expedia.ca/Chestertown-Hotels-Stunning-Historic-Downtown-Home-Within-2-Blocks-Of-Fountain-Park.h119124197.Hotel-Information)

10/10

Exceptional

(4 reviews)

"Overall a beautiful and well maintained place to stay! The location was perfect…within walking distance to everything! A very charming home! We were so happy we chose this property!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dawn B.

[](https://www.expedia.ca/Chestertown-Hotels-Stunning-Historic-Downtown-Home-Within-2-Blocks-Of-Fountain-Park.h119124197.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92930000/92922000/92921948/2eb71d3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/93000000/92930000/92922000/92921948/59d3c305.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/93000000/92930000/92922000/92921948/651f3001.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/93000000/92930000/92922000/92921948/35823b1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Tilghman Island

[](https://www.expedia.ca/Tilghman-Hotels-Heart-Of-Tilghman-Island-Pet-Friendly-Perfect-For-Weddings-Guests-Families.h92921948.Hotel-Information)

10/10

Exceptional

(14 reviews)

"Absolutely, amazing experience! Would highly recommend this house."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michael H.

[](https://www.expedia.ca/Tilghman-Hotels-Heart-Of-Tilghman-Island-Pet-Friendly-Perfect-For-Weddings-Guests-Families.h92921948.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/101000000/100800000/100794400/100794304/3322589a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100800000/100794400/100794304/849df086.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/101000000/100800000/100794400/100794304/fa5c5538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100800000/100794400/100794304/1ded8f20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Easton

[](https://www.expedia.ca/Easton-Hotels-Woodwind-Manor-On-The-Tred-Avon-Minutes-To-St-Michaels-And-Easton.h100794304.Hotel-Information)

10/10

Exceptional

(11 reviews)

"Great property for a family summer vacation and to just relax by the pool, kayak, fish off the dock, and head to town for ice cream or crabs."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveller

[](https://www.expedia.ca/Easton-Hotels-Woodwind-Manor-On-The-Tred-Avon-Minutes-To-St-Michaels-And-Easton.h100794304.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/34000000/33550000/33549200/33549150/5273b469.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)

![Exterior](https://images.trvl-media.com/lodging/34000000/33550000/33549200/33549150/4255a791.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33550000/33549200/33549150/3316dfa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Woolford

[](https://www.expedia.ca/Woolford-Hotels-Newer-Luxury-Waterfront-Beach.h33549150.Hotel-Information)

9.8/10

Exceptional

(75 reviews)

"We enjoyed our stay in Woolford. The day was filled with fishing, swimming and boating. Thank you again for sharing your property with our family."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Linda S.

[](https://www.expedia.ca/Woolford-Hotels-Newer-Luxury-Waterfront-Beach.h33549150.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34350000/34340300/34340251/fa7b7a6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34350000/34340300/34340251/c7bf430d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34350000/34340300/34340251/56b460e3.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)

### Vacation Home in Cambridge

[](https://www.expedia.ca/Cambridge-Hotels-Year-Round-Waterfront-Estate-Family-Reunions-Retreats-Sleeps-28.h34340251.Hotel-Information)

10/10

Exceptional

(82 reviews)

"There were so many activities and so many beds/baths. Perfect for a large group."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ellen S.

[](https://www.expedia.ca/Cambridge-Hotels-Year-Round-Waterfront-Estate-Family-Reunions-Retreats-Sleeps-28.h34340251.Hotel-Information)

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/68000000/67330000/67326000/67325935/1eb685d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67330000/67326000/67325935/589a71a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, video library](https://images.trvl-media.com/lodging/68000000/67330000/67326000/67325935/5bb44812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/68000000/67330000/67326000/67325935/782a7e19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Frederica

[](https://www.expedia.ca/Dover-Hotels-Captains-Quarters.h67325935.Hotel-Information)

9.8/10

Exceptional

(109 reviews)

"The house was perfect for our family weekend together, very clean and comfortable."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christine D.

CA $384

CA $727 total

includes taxes & fees

Mar 12 - Mar 13

[](https://www.expedia.ca/Dover-Hotels-Captains-Quarters.h67325935.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/93000000/92610000/92607300/92607228/f265549e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/93000000/92610000/92607300/92607228/f0af3f64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92610000/92607300/92607228/164b2f26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, offices](https://images.trvl-media.com/lodging/93000000/92610000/92607300/92607228/47b03627.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Sherwood

[](https://www.expedia.ca/Sherwood-Hotels-Time-Stands-Still.h92607228.Hotel-Information)

10/10

Exceptional

(22 reviews)

"This place is spacious, comfortable, and so clean. Well-maintained outdoor grounds, very nice and helpful caretaker, amazing to have access to boats/life jackets, golf cart, and fire pit!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Talia R.

[](https://www.expedia.ca/Sherwood-Hotels-Time-Stands-Still.h92607228.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33710000/33706000/33705957/c6b196d2.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)

![Interior](https://images.trvl-media.com/lodging/34000000/33710000/33706000/33705957/780a1972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33710000/33706000/33705957/fb9738e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cambridge

[](https://www.expedia.ca/Cambridge-Hotels-Waterfront-Family-Retreat-With-Gorgeous-Views-And-A-Large-Deepwater-Dock-5-MLW.h33705957.Hotel-Information)

9.8/10

Exceptional

(133 reviews)

"This was our second time staying here. Love the location and size of the property. Plenty of space for the kids to play catch, ride bikes, and lots of crabbing and fishing. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joe B.

[](https://www.expedia.ca/Cambridge-Hotels-Waterfront-Family-Retreat-With-Gorgeous-Views-And-A-Large-Deepwater-Dock-5-MLW.h33705957.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108390000/108385700/108385645/w1424h945x1y0-5f4c2bf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/109000000/108390000/108385700/108385645/w1439h942x1y0-5ae2e664.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/109000000/108390000/108385700/108385645/w1439h960x1y13-afb393d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/109000000/108390000/108385700/108385645/w1440h935x0y1-bd1d0668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in East New Market

[](https://www.expedia.ca/East-New-Market-Hotels-Belle-Aire-Landing-Spacious-Large-Estate-Under-New-Management.h108385645.Hotel-Information)

10/10

Exceptional

(2 reviews)

"Clean, well-appointed kitchen. Loved the crab shack!! Would highly recommend. Used the kayaks and canoe. The pool was perfect! The property is beautiful. Highly reccomend"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

kathleen l.

[](https://www.expedia.ca/East-New-Market-Hotels-Belle-Aire-Landing-Spacious-Large-Estate-Under-New-Management.h108385645.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/102000000/101080000/101073900/101073809/23ec8daf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/102000000/101080000/101073900/101073809/f6f97d7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, stereo, computer monitors](https://images.trvl-media.com/lodging/102000000/101080000/101073900/101073809/39e346f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, stereo, computer monitors](https://images.trvl-media.com/lodging/102000000/101080000/101073900/101073809/47368bc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Frederica

[](https://www.expedia.ca/Frederica-Hotels-Oceanview-Riverfront-Retreat-W-Hot-Tub-And-Private-Dock-10-Min-From-DE-Turf.h101073809.Hotel-Information)

10/10

Exceptional

(11 reviews)

"Very Interesting place to stayGood time had by all"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gregory H.

[](https://www.expedia.ca/Frederica-Hotels-Oceanview-Riverfront-Retreat-W-Hot-Tub-And-Private-Dock-10-Min-From-DE-Turf.h101073809.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.ca/Hotel-Search?startDate=2026-03-11&endDate=2026-03-12&regionId=553248635976434148&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## 

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Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

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## Find vacation rentals that suit your style

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Caroline+County%2C+Maryland%2C+United+States+of+America&regionId=553248635976434148&latLong=38.884558%2C-75.827156&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Caroline+County%2C+Maryland%2C+United+States+of+America&regionId=553248635976434148&latLong=38.884558%2C-75.827156&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=APARTMENT)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Caroline+County%2C+Maryland%2C+United+States+of+America&regionId=553248635976434148&latLong=38.884558%2C-75.827156&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=CONDO)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Caroline+County%2C+Maryland%2C+United+States+of+America&regionId=553248635976434148&latLong=38.884558%2C-75.827156&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=VILLA)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Caroline+County%2C+Maryland%2C+United+States+of+America&regionId=553248635976434148&latLong=38.884558%2C-75.827156&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=COTTAGE)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Caroline+County%2C+Maryland%2C+United+States+of+America&regionId=553248635976434148&latLong=38.884558%2C-75.827156&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=CABIN)

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## 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

"Good"

[](https://expedia.ca/Dover-Hotels-Dover-Downs-Hotel-Casino.h1572988.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

"The room was very large and had a separate entrance for the toilet and shower. Both had a sink in them. The room layout was wonderful. It made it feel like you had a living space with the couch and desk and "kitchen" area seperated from the sleeping area."

[](https://expedia.ca/Frederica-Hotels-Springhill-Suites-By-Marriott-Frederica.h95062671.Hotel-Information)

![Best Western Plus Easton Inn & Suites](https://images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/bedcc35b_y.jpg)

### Best Western Plus Easton Inn & Suites

10/10 Excellent

"Great local hotel. Best breakfast hands down!!! "

[](https://expedia.ca/Easton-Hotels-Best-Western-Plus-Easton-Inn-Suites.h6846089.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

"Room spotless"

[](https://expedia.ca/Seaford-Hotels-Days-Inn-Suites-By-Wyndham-Seaford.h1610385.Hotel-Information)

![Holiday Inn Express Hotel & Suites Dover by IHG](https://images.trvl-media.com/lodging/1000000/600000/597800/597727/6d0ff772_y.jpg)

### Holiday Inn Express Hotel & Suites Dover by IHG

10/10 Excellent

"Everything was excellent from check in to check out outstanding staff"

[](https://expedia.ca/Dover-Hotels-Holiday-Inn-Express-Hotel-Suites-Dover.h597727.Hotel-Information)

![The Tidewater Inn](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/fc311cc7_y.jpg)

### The Tidewater Inn

10/10 Excellent

"Wonderful staff. Comfortable space. Great food in Tavern. "

[](https://expedia.ca/Easton-Hotels-The-Tidewater-Inn.h1105532.Hotel-Information)

![Comfort Inn & Suites Dover near Speedway](https://images.trvl-media.com/lodging/2000000/1840000/1831100/1831095/c1d84f60_y.jpg)

### Comfort Inn & Suites Dover near Speedway

10/10 Excellent

"Wonderful stay !!!"

[](https://expedia.ca/Dover-Hotels-Comfort-Inn-Suites.h1831095.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

"Nicest hotel in a great spot"

[](https://expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information)

![Hyatt Regency Chesapeake Bay](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/6000a351_y.jpg)

### Hyatt Regency Chesapeake Bay

10/10 Excellent

"Just as one would expect with Hyatt hotel Great food, pool was really nice "

[](https://expedia.ca/Cambridge-Hotels-Hyatt-Regency-Chesapeake-Bay.h890486.Hotel-Information)

## Find out more about Caroline County

## Caroline County Vacation Homes information

| Number of reviews | 679                |
| ----------------- | ------------------ |
| Accommodation     | 311 Vacation Homes |
| Lowest Price      | CA $495            |
| Highest Price     | CA $727            |

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- [Flights to Eastern Shore ](https://www.expedia.ca/Cheap-Flights-To-Eastern-Shore.d6025644.Travel-Guide-Flights)
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- [Eastern Shore Vacations ](https://www.expedia.ca/Eastern-Shore.d6025644.Destination-Travel-Guides)
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- [Wye Landing ](https://www.expedia.ca/Wye-Landing-Wye-Mills.d553248621532662354.Vacation-Attraction)

- [Avis Rental Cars in Easton ](https://www.expedia.ca/Avis-Car-Rentals-In-Easton.d7120-c41.Car-Rental-Guide-Suppliers)
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- [Centreville Vacation Rentals ](https://www.expedia.ca/Centreville-Vacation-Rentals.d88125.Travel-Guide-VacationRentals)
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- [Book Vacation Homes in Caroline County on Expedia.com ](https://www.expedia.com/Caroline-County-Private-Vacation-Homes.d553248635976434148-aaPrivateVacationHomes.Travel-Guide-Accommodation)