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Georgetown Vacation Rentals

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Our top choices for Georgetown vacation rentals

1. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (130 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is CA $139
CA $222 total
includes taxes & fees
Oct 26 - Oct 27
First Floor Studio Apartment in Historic Chestertown

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, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is CA $165
CA $403 total
includes taxes & fees
Oct 25 - Oct 26
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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 $388 total
includes taxes & fees
Oct 26 - Oct 27
Secluded Cottage in Middle of Chestertown

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 $280
CA $442 total
includes taxes & fees
Oct 26 - Oct 27
BAYSIDE BUNGALOW

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 $315
CA $495 total
includes taxes & fees
Oct 26 - Oct 27
Newly restored apartment in the heart of Chestertown

6. 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 $244
CA $303 total
includes taxes & fees
Nov 2 - Nov 3
Beachcomber Suite

7. Turtle Cove Room

Turtle Cove Room
Kent County
The price is CA $227
CA $281 total
includes taxes & fees
Nov 2 - Nov 3
Turtle Cove Room

8. 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 $402 total
includes taxes & fees
Nov 2 - Nov 3
Cozy 1-bedroom in-law suite in lovely Chestertown with AC

9. Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (109 reviews)
"Wonderful stay. House boat was amazing and hosts helpful and responsive! "
United States
Jamie L.
The price is CA $139
CA $440 total
includes taxes & fees
Oct 27 - Oct 28
Cass-Away Luxury Houseboat

10. 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 $428
CA $676 total
includes taxes & fees
Nov 3 - Nov 4
Wren Retweet- Country Estate in Center of C’Town

11. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
Betterton
The price is CA $238
CA $486 total
includes taxes & fees
Oct 26 - Oct 27
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

12. 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, (11 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 $215 total
includes taxes & fees
Nov 9 - Nov 10
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

13. 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, (3 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 $221
CA $595 total
includes taxes & fees
Nov 2 - Nov 3
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

14. 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, (16 reviews)
"very wonderful home and very quite area "
United States
alan d.
The price is CA $279
CA $488 total
includes taxes & fees
Oct 27 - Oct 28
B’more Restful. Comfortable Townhome -Easy access to everywhere

15. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (8 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 $270
CA $675 total
includes taxes & fees
Oct 25 - Oct 26
Pool Loft Suite | Bay Access & Beach Passes

16. 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 $539 total
includes taxes & fees
Oct 25 - Oct 26
Abingdon Haven Hideaway

17. 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.
The price is CA $339
CA $428 total
includes taxes & fees
Nov 2 - Nov 3
Family Retreat at Lansdowne Manor

18. 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 $504
CA $931 total
includes taxes & fees
Oct 26 - Oct 27
Chesapeake Cottages- 2 Quaint Waterfront Retreats

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 $410
CA $805 total
includes taxes & fees
Oct 25 - Oct 26
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?

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.