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Georgetown Vacation Rentals

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Our top choices for Georgetown vacation rentals

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (118 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is CA $139
CA $223 total
includes taxes & fees
Jul 21 - Jul 22
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, (25 reviews)
"Kitchen was fully stocked, apartment very clean, very nice host and parking was great"
United States
Tara K.
The price is CA $165
CA $404 total
includes taxes & fees
Jul 21 - Jul 22
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (59 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is CA $252
CA $391 total
includes taxes & fees
Jul 26 - Jul 27
BAYSIDE BUNGALOW

Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is CA $257
CA $398 total
includes taxes & fees
Jul 27 - Jul 28
Secluded Cottage in Middle of Chestertown

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 CA $273
CA $544 total
includes taxes & fees
Jul 27 - Jul 28
Bayside Cottage steps from Rock Hall Harbor

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is CA $316
CA $531 total
includes taxes & fees
Jul 21 - Jul 22
Waterfront Retreat with Private Dock and Beach

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 CA $212
CA $262 total
includes taxes & fees
Jul 27 - Jul 28
Beachcomber Suite

Turtle Cove Room

Turtle Cove Room
Kent County
The price is CA $197
CA $244 total
includes taxes & fees
Jul 27 - Jul 28
Turtle Cove Room

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 CA $162
CA $323 total
includes taxes & fees
Jul 21 - Jul 22
Gorgeous 3-bedroom townhome with AC in friendly Dundalk

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 CA $250
CA $297 total
includes taxes & fees
Aug 3 - Aug 4
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

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 CA $247
CA $692 total
includes taxes & fees
Jul 24 - Jul 25
Idyllic Pasadena Retreat with Garden + Hot Tub!

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is CA $358
CA $769 total
includes taxes & fees
Aug 3 - Aug 4
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 CA $314
CA $681 total
includes taxes & fees
Jul 24 - Jul 25
Idyllic Pasadena Retreat With Garden + Hot Tub!

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 CA $164
CA $534 total
includes taxes & fees
Aug 1 - Aug 2
Abingdon Haven Hideaway

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 CA $293
CA $705 total
includes taxes & fees
Aug 1 - Aug 2
Pool Loft Suite | Bay Access & Beach Passes

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 CA $339
CA $959 total
includes taxes & fees
Jul 21 - Jul 22
Annapolis Home | Fenced Yard | Pool Table | 10 Guests

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 CA $505
CA $932 total
includes taxes & fees
Jul 21 - Jul 22
Chesapeake Cottages- 2 Quaint Waterfront Retreats

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 CA $574
CA $1,032 total
includes taxes & fees
Jul 23 - Jul 24
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Georgetown?

Yes, there are vacation rentals close to well known points of interest in Georgetown, or you can go with a more remote option if you want a relaxing place to stay.

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

Stay in the landmark Lighthouse!: This vacation home near Georgetown offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

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 larger area.

What are vacation rentals like in Georgetown?

Vacation rentals are private accommodations you can stay in for several days or more in Georgetown. Vacation rentals feature amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family trips or small group gatherings.