Caroline County Holiday Rentals

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Top Holiday Rentals Destinations in Caroline County

Captain's Quarters

9.8 out of 10, Exceptional, (97)
"We had a great weekend stay for a tournament. Thank you!"
Captain's Quarters

3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind

10.0 out of 10, Exceptional, (2)
"Place was amazing. Super clean and host let us snacks and flowers, nice touch. Just wish zi would have asked if the pool access was inckuded. That is the only thing that could have made it any better. 10/10 recommend "
The price is NZ$1,143
includes taxes & fees
13 Aug - 14 Aug
3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind

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

9.8 out of 10, Exceptional, (130)
"Great house, host and location. Stayed with a larger group and plenty of room!"
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf

9.4 out of 10, Exceptional, (3)
"Adorable cottage. Excellent location. We will definitely rent again. "
Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf

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

10.0 out of 10, Exceptional, (7)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

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

9.6 out of 10, Exceptional, (121)
"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (34)
"We really enjoyed our stay. Looking forward to staying again!"
The price is NZ$545
includes taxes & fees
7 Sept - 8 Sept
Cass-N-Reel Luxury Houseboat

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (103)
"Secluded"
Secluded Waterfront Cottage on 200 acre farm near Queenstown

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (253)
"What a wonderful area on the water. The proprietors were such friendly and accommodating people. The apartment was clean and well stocked. They had a wide range of activities on the property. It was wonderful being able to sit near the water and enjoy my friend’s company. I highly recommend this welcoming place. "
Family and Pet-Friendly, Waterfront with Pier

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (184)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

9.6 out of 10, Exceptional, (29)
"Very roomy and lots of amenities. Superb location and private. Easy check-in and check-out. Guest contact was awesome - very responsive! Thanks so much!"
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.8 out of 10, Exceptional, (11)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is NZ$840
includes taxes & fees
8 Sept - 9 Sept
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

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

9.8 out of 10, Exceptional, (40)
"Property was perfect for our family stay. House was clean and well stocked."
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!

10.0 out of 10, Exceptional, (23)
"The house was amazing, and close to Killens Pond State Park where we had additional family camping."
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!

St. Michaels Waterfront Home

9.8 out of 10, Exceptional, (31)
"We had a wonderful stay. Check in and out was very easy. The place was clean and well maintained. Very peaceful spot on the water. "
St. Michaels Waterfront Home

Mini Aruba Glamper inDover with WiFi, AC and guest access to backyard oasis

10.0 out of 10, Exceptional, (2)
"My husband and I stayed for two nights. The oasis makes you feel like you’re vacationing in the Caribbean. The camper is clean and comfortable for two people. Everything was perfect and cannot wait to return!"
The price is NZ$377
includes taxes & fees
11 Sept - 12 Sept
Mini Aruba Glamper inDover with WiFi, AC and guest access to backyard oasis

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

9.4 out of 10, Exceptional, (3)
"The place was very clean and in the most perfect spot in downtown Cambridge. We had a wedding walking distance from this place. Jen is a very responsive and accommodating host!"
The price is NZ$513
includes taxes & fees
19 Aug - 20 Aug
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Walk to Everything House

10.0 out of 10, Exceptional, (81)
"Clean and nice place to stay"
Walk to Everything House

Poe Themed Home Close to Beaches and DE Turf

10.0 out of 10, Exceptional, (2)
"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. "
The price is NZ$467
includes taxes & fees
18 Aug - 19 Aug
Poe Themed Home Close to Beaches and DE Turf

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

10.0 out of 10, Exceptional, (35)
"Great stay"
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
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