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Kent County Holiday Rentals

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Top Holiday Rentals Destinations in Kent County

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

10.0 out of 10, Exceptional, (32)
"Beautiful home, beautiful property! My family meets up annually and the house fit us perfectly. Plenty of room to spread out and congregate together. The home also provides so much to do with all the amenities! Thanks for the memories "
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (24)
"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Baltimore executive Furnished rentals

4.0 star property
8.0 out of 10, Very good, (2)
"I highly recommend this property if you’re visiting the Baltimore area. Very spacious for myself, my husband and our 4 kids. Lorraine checked in on us every other day and Mr. Derrick made sure everything was in order upon our arrival."
The price is AU$825
includes taxes & fees
2 Mar - 3 Mar
Baltimore executive Furnished rentals

Spectacular Penthouse at 39 west.

4.0 star property
The price is AU$645
includes taxes & fees
14 Feb - 15 Feb
Spectacular Penthouse at 39 west.

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (22)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino

9.6 out of 10, Exceptional, (21)
"Couldn't ask for a better location for walking to The Bank. Parking pass good on game days. Had no problem parking right out front. Excellent communication with host and house was very nicely appointed! Stairs wider and safer than most in Pigtown"
⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (206)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Rooftop Deck Escape! Free Parking!

9.0 out of 10, Wonderful, (25)
"We had a great time, plenty of space for family of 8 with close distance to the aquarium. "
The price is AU$458
includes taxes & fees
2 Feb - 3 Feb
Rooftop Deck Escape! Free Parking!

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (21)
"We really enjoyed our stay. Looking forward to staying again!"
The price is AU$478
includes taxes & fees
19 Feb - 20 Feb
Cass-N-Reel Luxury Houseboat

Fantastic 2 bedrooms apt. Harbor

4.0 star property
10.0 out of 10, Exceptional, (1)
"It was a nice place"
Fantastic 2 bedrooms apt. Harbor

'At Fells Point' CitySide - 'Tons better than a hotel!'

9.8 out of 10, Exceptional, (183)
"Great location. Walking distance to Fells point and Canton. Tavern right next door. Nice people there. Cozy place. Clean and comfortable. "
The price is AU$330
includes taxes & fees
4 Feb - 5 Feb
'At Fells Point' CitySide - 'Tons better than a hotel!'

Luxe Houseboat: Breathtaking Skyline 360 Views

10.0 out of 10, Exceptional, (12)
"Gorgeous floating home - wonderful windows to appreciate the fabulous water views Excellent rooftop space - comfy bed and sleep sofa - beautifully appointed kitchen and bathroom "
The price is AU$1,086
includes taxes & fees
5 Feb - 6 Feb
Luxe Houseboat: Breathtaking Skyline 360 Views

Beachfront Sunsets on the Water at Oakwood Beach

10.0 out of 10, Exceptional, (31)
"We had a nice visit to this beautiful, waterfront home, and appreciated the host very much. The views from the beach were lovely. Unfortunately, we were woken several times overnight one night by ships’ foghorns as they passed by- every few hours. Even the white noise machines (a thoughtful touch) didn’t help. Not sure how to predict when the ships come through, but we slept soundly the second of our two nights there. The area is otherwise very quiet- we barely saw anyone else around. The...
Beachfront Sunsets on the Water at Oakwood Beach

Chase at Light

4.0 star property
2.0 out of 10, (2)
"What was listed as a Deluxe Penthouse apartment was far from it. - As a city girl. I am familiar with city-life. Nevertheless, to be greeted by a few shady-looking characters in the front of the building, did not make me, or my grandchildren, feel secure. - Upon entering the apartment, the lights did not work in "the dining room" and part of the kitchen. There were two red vinyl upholstered chairs around a small dining room table with large damage to their faux leather covers. - The pullout...
Chase at Light

Welcome to the Charm City Getaway!

9.4 out of 10, Exceptional, (3)
"We had a pleasant stay in Mr. Farrow’s home. It’s spacious, clean, and felt like home. Doc made sure we had everything we needed. We barely noticed that he was sharing his home with us. He was very accommodating to our needs and responded to us within a reasonable time. We would definitely stay here again."
The price is AU$679
includes taxes & fees
23 Feb - 24 Feb
Welcome to the Charm City Getaway!

Stunning waterfront villa with indoor pool and kids swing set and play area.

9.8 out of 10, Exceptional, (13)
"The house was beautiful. We enjoyed the pool. The kitchen was wonderful. We did wish we could warm up the house a little more. We loved that the house had so many bathrooms. The only improvement would be to state that there are 5 bedrooms with en-suites."
Stunning waterfront villa with indoor pool and kids swing set and play area.

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

9.8 out of 10, Exceptional, (172)
"Host was amazing. Property is perfect. Will be staying here again. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Guest Lodge | Private Pool | Outdoor Dining | Game Room

Guest Lodge | Private Pool | Outdoor Dining | Game Room
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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