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Top Holiday Rentals in Georgetown

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (31)
"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

9.8 out of 10, Exceptional, (61)
"Awesome place!"
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

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 £246
includes taxes & fees
7 Sept - 8 Sept
Cass-N-Reel Luxury Houseboat

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (301)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina

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

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

9.4 out of 10, Exceptional, (89)
"What a wonderful vacation we had everything you want is there. All you have to bring is food . The trampoline will keep everyone occupied for hours. Looking forward to staying there in the future."
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!

10.0 out of 10, Exceptional, (93)
"We stay at Firefly every time we go to visit our son and his family. It works perfectly for us…an oasis for us, and a fun place for the kids to visit, too. Pat and Ken have been the perfect hosts!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!

Waterfront Oasis w/ Private Dock, 3BR/2BA

9.4 out of 10, Exceptional, (34)
"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "
Waterfront Oasis w/ Private Dock, 3BR/2BA

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (37)
"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "
Historic Downtown Garden Oasis with Private Patio

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (42)
"This is a jewel as it is private, peaceful with lovely setting."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (43)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is £227
includes taxes & fees
11 Aug - 12 Aug
BAYSIDE BUNGALOW

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

10.0 out of 10, Exceptional, (6)
"Relaxing and stunning location. Beautiful bay front property with stunning views of the bay. If you are looking for a quiet and peaceful getaway that involves wildlife sightings this is the perfect spot. Well equipped and roomy rental. Very clean too. "
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

Kent Island Waterfront Cottage

8.8 out of 10, Excellent, (11)
"Enjoyed fishing at the pier and sitting on the porch"
Kent Island Waterfront Cottage

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

10.0 out of 10, Exceptional, (54)
"Great location with a great view."
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Eastern Shore beach cottage get-away

10.0 out of 10, Exceptional, (136)
"This house was the cutest little place right across the street from the beach with a beautiful view. The house was clean and had all the amenities needed for our stay. We would definitely stay there again!"
Eastern Shore beach cottage get-away

Charming, updated 1930's beachfront cottage with stunning sunset views

10.0 out of 10, Exceptional, (1)
"Check in was a breeze. Place was clean. Simply beautiful. Most relaxing place ever. "
Charming, updated 1930's beachfront cottage with stunning sunset views

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

9.8 out of 10, Exceptional, (31)
"The property was very nice. It felt so homey. Clean and nicely appointed, even decorated for Christmas! In 2 short days ther was so much laughter and memories made! We would definitely recommend this home for a family stay!and memories made!"
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

Luxury Waterfront Executive Family Home Annapolis with All Amenities

10.0 out of 10, Exceptional, (2)
"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "
Luxury Waterfront Executive Family Home Annapolis with All Amenities

Waterfront Annapolis Home: Fire Pit & Fishing Pier

9.2 out of 10, Wonderful, (37)
"It was a great place to enjoy family / family friend time with our sons away at college playing baseball nearby. It was lovely backyard to play corn hole with everyone and dog friendly. Enjoyed morning coffe with relaxing creek setting. Boys enjoyed fishing from the dock. Loved the scrabble game. "
Waterfront Annapolis Home: Fire Pit & Fishing Pier

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (93)
"Very pretty location. Few minutes drive to town center."
The price is £121
includes taxes & fees
13 Aug - 14 Aug
First Floor Studio Apartment in Historic Chestertown
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 Georgetown Hotel Reviews

Frequently asked questions

Are there holiday rentals in Georgetown?

Yes, there are holiday rentals close to the most popular sights in Georgetown, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Georgetown has to offer?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Georgetown offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Georgetown?

Explore the area and family-friendly sights such as Hazel Miner Monument, or get out into nature at a spot like Ferry Park. The Mainstay and Rock Hall Harbor are a couple of places you'll find in the wider area.

What are holiday rentals like in Georgetown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Georgetown. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great option for small groups.