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Georgetown Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is CA $138
CA $210 total
includes taxes & fees
Nov 9 - Nov 10
First Floor Studio Apartment in Historic Chestertown
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

2. 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, (33 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is CA $172
CA $391 total
includes taxes & fees
Nov 6 - Nov 7
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A garden with a wooden bridge, lush greenery, and a variety of plants.

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.
The price is CA $257
CA $367 total
includes taxes & fees
Nov 7 - Nov 8
Secluded Cottage in Middle of Chestertown
A building with a gabled roof and a circular vent on the roof.

4. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is CA $279
CA $420 total
includes taxes & fees
Nov 6 - Nov 7
BAYSIDE BUNGALOW
A spacious living area with a dining table, sofa, and a kitchen in the background.

5. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (34 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
The price is CA $314
CA $470 total
includes taxes & fees
Nov 11 - Nov 12
Newly restored apartment in the heart of Chestertown
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

6. Turtle Cove Room

Turtle Cove Room
Kent County
10.0 out of 10, Exceptional, (1 review)
"The host was very communicative. The room was clean. It was quiet and peaceful. There were blackout curtains on the windows. A very pleasant stay."
United States
Jennifer M.
The price is CA $226
CA $267 total
includes taxes & fees
Nov 23 - Nov 24
Turtle Cove Room
A covered porch with a wooden bench, potted plants, and a decorative railing.

7. 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.
The price is CA $426
CA $638 total
includes taxes & fees
Nov 15 - Nov 16
Wren Retweet- Country Estate in Center of C’Town
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

8. 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 $243
CA $287 total
includes taxes & fees
Nov 23 - Nov 24
Beachcomber Suite
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

9. 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.
The price is CA $277
CA $388 total
includes taxes & fees
Nov 13 - Nov 14
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

10. 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, (12 reviews)
"Beautiful location, nicely decorated. The host thought of everything you may need including a free snack basket, washer/dryer with detergent and dryer sheets, BBQ grill with utensils, board games and cards, kayaks and life vests, hot tub, firetable etc."
United States
Andy W.
The price is CA $175
CA $203 total
includes taxes & fees
Nov 11 - Nov 12
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
A sunset view from a balcony with a glass-top table and a fire feature, overlooking the sea.

11. 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, (4 reviews)
"We had a phenomenal time celebrating our engagement at Flohom! The space was spotlessly clean, super comfortable, and peaceful. The location was fantastic, and the hosting was top-notch from start to finish. We couldn't have asked for a better experience to"
United States
Charles W.
The price is CA $259
CA $611 total
includes taxes & fees
Nov 8 - Nov 9
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
A deck with a view of a marina, including boats and docks.

12. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (54 reviews)
"Love This rental. One of our favorites. Small but everything needed. And the view is absolutely wonderful."
United States
Yamilet
The price is CA $126
CA $362 total
includes taxes & fees
Nov 12 - Nov 13
Cass-N-Reel Luxury Houseboat
A modern kitchen with stainless steel appliances, white cabinetry, and a brick backsplash.

13. 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, (18 reviews)
"very wonderful home and very quite area "
United States
alan d.
The price is CA $259
CA $439 total
includes taxes & fees
Nov 10 - Nov 11
B’more Restful. Comfortable Townhome -Easy access to everywhere
A kitchen with wooden cabinets, a dining table, and a refrigerator.

14. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (14 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.
The price is CA $321
CA $386 total
includes taxes & fees
Nov 9 - Nov 10
Family Retreat at Lansdowne Manor
Stylish kitchen with open layout and island seating

15. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (9 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 $292
CA $645 total
includes taxes & fees
Nov 12 - Nov 13
Pool Loft Suite | Bay Access & Beach Passes
A wooden dock with Adirondack chairs and a ladder, overlooking a calm body of water with a distant shoreline.

16. 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.
The price is CA $503
CA $841 total
includes taxes & fees
Nov 9 - Nov 10
Chesapeake Cottages- 2 Quaint Waterfront Retreats
A hot tub area with a covered patio, outdoor seating, and a view of the surrounding landscape.

17. Idyllic Pasadena Retreat with Garden + Hot Tub!

Idyllic Pasadena Retreat with Garden + Hot Tub!
Green Haven
10.0 out of 10, Exceptional, (38 reviews)
"Place was very accommodating for our needs!"
United States
Antonia P.
The price is CA $246
CA $656 total
includes taxes & fees
Nov 15 - Nov 16
Idyllic Pasadena Retreat with Garden + Hot Tub!
A kitchen with wooden cabinets, a stove, and a dining table with chairs.

18. Family Friendly Cozy 3 Bedroom Duplex

Family Friendly Cozy 3 Bedroom Duplex
Grasonville
The price is CA $377
CA $435 total
includes taxes & fees
Nov 6 - Nov 7
Family Friendly Cozy 3 Bedroom Duplex
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

19. 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
9.2 out of 10, Wonderful, (19 reviews)
"Quiet neighborhood, worked well for our group of 8."
United States
Jennifer H.
The price is CA $434
CA $769 total
includes taxes & fees
Nov 8 - Nov 9
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

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

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

8/10 Good
"This was a short stay and a pleasant experience. Breakfast was ok, and yet, very limited."
Eliezer 1-night trip
Posted 1 hour 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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Georgetown vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Georgetown vacation rentals we have selected for you start as low as CA $203 per night. Entering your travel dates in the search wizard 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.