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Georgetown Holiday Rentals

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Our top choices for Georgetown holiday rentals

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (118 reviews)
"We had a lovely stay at Elisabeths place. She helped us with anything we needed. The aprtment was clean, cozy and just right for 2 people."
United States
Lisa v.
The price is NZ$272
includes taxes & fees
21 July - 22 July
First Floor Studio Apartment in Historic Chestertown

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (24 reviews)
"Kitchen was fully stocked, apartment very clean, very nice host and parking was great"
United States
Tara K.
The price is NZ$490
includes taxes & fees
17 July - 18 July
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (58 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is NZ$507
includes taxes & fees
28 July - 29 July
BAYSIDE BUNGALOW

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is NZ$645
includes taxes & fees
29 July - 30 July
Waterfront Retreat with Private Dock and Beach

Gorgeous 3-bedroom townhome with AC in friendly Dundalk

Gorgeous 3-bedroom townhome with AC in friendly Dundalk
Dundalk
6.0 out of 10, (4 reviews)
"Overall you’re getting what you pay for. The downstairs toilet didn’t work and there weren’t any towels or lotion but the place was spacey and nice"
United States
Tobi A.
The price is NZ$400
includes taxes & fees
20 July - 21 July
Gorgeous 3-bedroom townhome with AC in friendly Dundalk

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is NZ$865
includes taxes & fees
3 Aug - 4 Aug
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
The price is NZ$836
includes taxes & fees
19 July - 20 July
Idyllic Pasadena Retreat With Garden + Hot Tub!

Turtle Cove Room

Turtle Cove Room
Kent County
The price is NZ$300
includes taxes & fees
3 Aug - 4 Aug
Turtle Cove Room

Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
The price is NZ$318
includes taxes & fees
27 July - 28 July
Beachcomber Suite

Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (5 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is NZ$856
includes taxes & fees
1 Aug - 2 Aug
Pool Loft Suite | Bay Access & Beach Passes

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
10.0 out of 10, Exceptional, (2 reviews)
"Had a great weekend celebrating our anniversary. The property was beautiful and right on the water. We enjoyed kayaking and watching the sunset over the river."
United States
Warren B.
The price is NZ$361
includes taxes & fees
3 Aug - 4 Aug
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is NZ$614
includes taxes & fees
28 July - 29 July
Bayside Cottage steps from Rock Hall Harbor

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (23 reviews)
"Excellent Property"
United States
Buu T.
The price is NZ$1,134
includes taxes & fees
29 July - 30 July
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Abingdon Haven Hideaway

Abingdon Haven Hideaway
Abingdon
7.0 out of 10, Good, (2 reviews)
"We made good use of this rental, it was convenient to all our family & activities. Host is very kind & quickly helpful on request. The main problem with a basement apt is that the thermostat is usually upstairs in the main house, but host was most accommodating about temperature control. We rested well here and had a nice week."
United States
Pam L.
The price is NZ$651
includes taxes & fees
14 Aug - 15 Aug
Abingdon Haven Hideaway

Idyllic Pasadena Retreat with Garden + Hot Tub!

Idyllic Pasadena Retreat with Garden + Hot Tub!
Green Haven
10.0 out of 10, Exceptional, (35 reviews)
"Place was very accommodating for our needs!"
United States
Antonia P.
The price is NZ$840
includes taxes & fees
19 July - 20 July
Idyllic Pasadena Retreat with Garden + Hot Tub!

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Cape Saint Claire
9.0 out of 10, Wonderful, (14 reviews)
"Dominick was a great communicator, he was very responsive and ensured we were comfortable during this stay. Highly recommend anyone to book this property!"
United States
Marissa F.
The price is NZ$1,180
includes taxes & fees
19 July - 20 July
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.6 out of 10, Exceptional, (12 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is NZ$1,179
includes taxes & fees
21 July - 22 July
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
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

Find out more about Georgetown

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Georgetown holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Georgetown. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Georgetown. Seeing all the best attractions is bound to make you fall in love with Georgetown. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Georgetown short-term rentals, that won’t be hard to do.

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 Crumpton Auction, or get out into nature at a spot like Miami Beach. 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.