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Georgetown Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Georgetown vacation rentals

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

1. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (125 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
$144 nightly
The price is $159
Sep 29 - Sep 30
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
A building with a gabled roof and a circular vent on the roof.

2. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (65 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
$286 nightly
The price is $316
Sep 27 - Sep 28
Total with taxes and fees
BAYSIDE BUNGALOW
A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

3. 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.
$264 nightly
The price is $274
Sep 29 - Sep 30
Total with taxes and fees
Secluded Cottage in Middle of Chestertown
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

4. 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, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
$266 nightly
The price is $294
Sep 27 - Sep 28
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A garden with a variety of plants and a small bridge.

5. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
$463 nightly
The price is $481
Sep 27 - Sep 28
Total with taxes and fees
Wren Retweet- Country Estate in Center of C’Town
A spacious living room with a leather sofa, a wooden coffee table, and a fireplace.

6. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (5 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
$365 nightly
The price is $387
Sep 27 - Sep 28
Total with taxes and fees
Bayside Cottage steps from Rock Hall Harbor
A modern exterior with a black door, a metal staircase, and a lantern.

7. Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (107 reviews)
"Wonderful stay. House boat was amazing and hosts helpful and responsive! "
United States
Jamie L.
$273 nightly
The price is $301
Sep 28 - Sep 29
Total with taxes and fees
Cass-Away Luxury Houseboat
A sandy beach with a wooden walkway leading to a calm lake, surrounded by dense green foliage.

8. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
9.8 out of 10, Exceptional, (27 reviews)
"Everything was lovely! The dock was beautiful and the accommodations were comfortable.Thanks!"
United States
Max G.
$286 nightly
The price is $316
Oct 4 - Oct 5
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
A modern kitchen with dark cabinets, a white countertop, and a large window.

9. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (51 reviews)
"Had a great time, great property and great location."
United States
Danny B.
$243 nightly
The price is $268
Oct 8 - Oct 9
Total with taxes and fees
Cass-N-Reel Luxury Houseboat
A living room with a brown leather sofa, a wooden coffee table, and a ceiling fan.

10. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
$293 nightly
The price is $311
Oct 5 - Oct 6
Total with taxes and fees
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A modern kitchen with stainless steel appliances, white cabinetry, and a brick backsplash.

11. B’more Restful. Comfortable Townhome -Easy access to everywhere

B’more Restful. Comfortable Townhome -Easy access to everywhere
Dundalk
10.0 out of 10, Exceptional, (15 reviews)
"very wonderful home and very quite area "
United States
alan d.
$277 nightly
The price is $320
Sep 27 - Sep 28
Total with taxes and fees
B’more Restful. Comfortable Townhome -Easy access to everywhere
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

12. Turtle Cove Room

Turtle Cove Room
Kent County
$176 nightly
The price is $191
Sep 28 - Sep 29
Total with taxes and fees
Turtle Cove Room
A wooden dock with Adirondack chairs and a ladder, overlooking a calm body of water with a distant shoreline.

13. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (24 reviews)
"Excellent Property"
United States
Buu T.
$583 nightly
The price is $665
Sep 28 - Sep 29
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

14. 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.
$174 nightly
The price is $189
Sep 28 - Sep 29
Total with taxes and fees
Beachcomber Suite
A hot tub area with a covered patio, outdoor seating, and a view of the surrounding landscape.

15. Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
$426 nightly
The price is $485
Oct 8 - Oct 9
Total with taxes and fees
Idyllic Pasadena Retreat With Garden + Hot Tub!
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

16. 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, (16 reviews)
"Quiet neighborhood, worked well for our group of 8."
United States
Jennifer H.
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

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

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
9.8 out of 10, Exceptional, (8 reviews)
"The host was incredibly friendly and communicative. The place was a lot bigger than I expected, and it was beautiful to sit out by the fire pit and look at the river nearby. And, she left us snacks and smores for the stay! A nice quiet spot to spend a night."
United States
Matthew
$175 nightly
The price is $186
Sep 27 - Sep 28
Total with taxes and fees
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

18. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
$479 nightly
The price is $508
Sep 25 - Sep 26
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
A sunset view from a balcony with a glass-top table and a fire feature, overlooking the sea.

19. FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
10.0 out of 10, Exceptional, (2 reviews)
"FLOHOM 14 did not disappoint!!! This was my first stay on a houseboat. Now I know why babies fall asleep when rocked. The boat is beautifully appointed & well equipped. Bring a good book. I’m already missing it!!!"
United States
Maria D.
$381 nightly
The price is $434
Sep 28 - Sep 29
Total with taxes and fees
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
A kitchen with wooden cabinets, a dining table, and a refrigerator.

20. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (13 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
$379 nightly
The price is $419
Sep 30 - Oct 1
Total with taxes and fees
Family Retreat at Lansdowne Manor
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

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

10/10 Excellent
"Stayed here before and service is still superb"
Ebony 2-night trip
Posted 12 hours ago
Quality Inn & Suites Bel Air I-95 Exit 77A

Find out more about Georgetown

Everything you need to know about Georgetown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Georgetown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Georgetown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Georgetown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Georgetown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Georgetown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $186 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Georgetown rentals

At Expedia, we put the best Georgetown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Georgetown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Georgetown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Georgetown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This vacation home rental near Georgetown offers a balcony, a garden, and a barbecue grill 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 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. Rock Hall Harbor and Washington College 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.