Vacation Rentals in Caroline County

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Top Vacation Rentals in Caroline County

Marina
Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat

Grasonville
10.0 out of 10, Exceptional, (47)
"Amazing views! Location is great, restaurants at walking distance, great bicicle trail, highly recommended!"
United States
Oliver C.
Cass-N-Reel Luxury Houseboat
Terrace/patio
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Cambridge
10.0 out of 10, Exceptional, (80)
"Great for 10 adults and 4 grandchildren!"
United States
Phil S.
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (107)
"Amazing and neat and very private "
United States
Alexander M.
The price is ￥15,462
￥24,808 total
includes taxes & fees
Dec 1 - Dec 2
First Floor Studio Apartment in Historic Chestertown
Exterior
Cozy cottage on the Miller farm.

Cozy cottage on the Miller farm.

Milford
10.0 out of 10, Exceptional, (240)
"We’ve stayed here several timesWe always feel welcome and the cottage is perfect!!"
United States
Ron F.
Cozy cottage on the Miller farm.
Fridge, microwave, oven, stovetop
Captain's Quarters

Captain's Quarters

Frederica
9.8 out of 10, Exceptional, (103)
"This our second time staying here and we absolutely love it! Looking forward to staying here again in May 2026. "
United States
Criselle A.
Captain's Quarters
Exterior detail
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cambridge
10.0 out of 10, Exceptional, (15)
"Well equipped and super clean; great place!"
United States
Steve S.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
3 bedrooms, iron/ironing board, WiFi, bed sheets
Delaware Turf Bungalow’s Sister!

Delaware Turf Bungalow’s Sister!

Milford
10.0 out of 10, Exceptional, (2)
"This bungalow was the perfect getaway for the weekend. It was clean, cozy and had enough space for my children and I to relax without being on top of each other. We were close enough to several beaches and the boardwalk but far enough away to get away from the hustle and bustle of the big beach town. The host was amazing. She was so nice to communicate with and very accommodating. She made us feel very welcomed and even suggested some sights to check out around the area. The whole experience was...
United States
Christina T.
Delaware Turf Bungalow’s Sister!
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

St. Michaels
9.8 out of 10, Exceptional, (44)
"Wonderful home in excellent location!!"
United States
Sydney S.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Exterior
Modern Flat in the Heart of St. Michaels – Walk Everywhere

Modern Flat in the Heart of St. Michaels – Walk Everywhere

Saint Michaels
9.8 out of 10, Exceptional, (56)
"Such a beautiful space in a perfect location! We were able to walk to everything — shops, restaurants, farmers market, waterfront, etc! Highly recommend!"
United States
Paige R.
Modern Flat in the Heart of St. Michaels – Walk Everywhere
Outdoor pool
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Cambridge
9.8 out of 10, Exceptional, (7)
"Wow! What an incredible property and house. We were a group of families with small kids, and it was heaven for them playing in the pool, on the dock, on the playground, and in the expansive yard. Lots of beautiful sunsets on the patio for the grown-ups too. We never had to leave. Can't recommend highly enough. "
United States
Lea F.
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Private beach
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

Sherwood
10.0 out of 10, Exceptional, (20)
"Fantastic property"
United States
Harvey W.
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Fridge, microwave, oven, stovetop
Waterfront! Private Dock, Boat Tie-Up & Near Town

Waterfront! Private Dock, Boat Tie-Up & Near Town

Rock Hall
10.0 out of 10, Exceptional, (2)
"A beautiful spot."
United States
Laura S.
Waterfront! Private Dock, Boat Tie-Up & Near Town
Dining
Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat

Grasonville
10.0 out of 10, Exceptional, (104)
"What a unique experience to stay on a houseboat. Such a fun locale & comfortable accommodations. "
United States
Robin L.
Cass-Away Luxury Houseboat
Exterior
Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier

Cambridge
10.0 out of 10, Exceptional, (264)
"The property, house and amenities were exactly as described. Absolutely gorgeous views second only to the hospitality extended by Rob and Clarissa!"
United States
Tom K.
Family and Pet-Friendly, Waterfront with Pier
Marina
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

St Michaels
9.6 out of 10, Exceptional, (125)
"Prime location! "
United States
Cindy V.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Outdoor dining
Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Rock Hall
10.0 out of 10, Exceptional, (73)
"This trip was a girls get away & we thoroughly enjoyed ourselves .. the house was by far the best I’ve ever rented .. clean, well appointed, & decor was gorgeous … the owner was so attentive & acted on anything we needed right away .. I highly recommend this property & we will definitely be returning …"
United States
Denise O.
Waterfront Paradise on the Eastern Shore of Chesapeake Bay
Property grounds
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St Michaels
9.6 out of 10, Exceptional, (147)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
United States
maggie k.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Terrace/patio
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Cambridge
9.8 out of 10, Exceptional, (133)
"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
Joe B.
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Fridge, microwave, oven, stovetop
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

Royal Oak
10.0 out of 10, Exceptional, (90)
"5 out of 5. Beautiful, well kept property across aspects. Comfortably accommodated our group of 14. Excellent communication with the Renter and felt as though we were borrowing the property from a family friend. Would recommend to anyone!"
United States
Katie M.
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
Marina
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Easton
10.0 out of 10, Exceptional, (95)
"Gorgeous views and surroundings"
United States
Robin P.
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
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.
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Top Caroline County Hotel Reviews

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"The hotel was very clean, and staff was courteous and helpful "
Audrey 2-night trip
Posted 3 days ago
Hyatt Place Kent Narrows & Marina

Find out more about Caroline County

Vacation Apartments in Caroline County

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