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Upfront pricingWe are not like the others - we include taxes and fees
Our top choices for Georgetown vacation rentals
1. First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic ChestertownChestertown
9.8 out of 10, Exceptional, (133 reviews)
"A beautiful and comfortable accomodations."
John R.
$133 nightly
The price is $147
Nov 9 - Nov 10
Total with taxes and fees
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"
lisa p.
$253 nightly
The price is $280
Nov 12 - Nov 13
Total with taxes and fees
3. Secluded Cottage in Middle of Chestertown
Secluded Cottage in Middle of ChestertownChestertown
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."
Amy D.
$257 nightly
The price is $267
Nov 9 - Nov 10
Total with taxes and fees
4. BAYSIDE BUNGALOW
BAYSIDE BUNGALOWRock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
Diane V.
$264 nightly
The price is $292
Nov 9 - Nov 10
Total with taxes and fees
5. Newly restored apartment in the heart of Chestertown
Newly restored apartment in the heart of ChestertownChestertown
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!"
Susan A.
$296 nightly
The price is $328
Nov 9 - Nov 10
Total with taxes and fees
6. Turtle Cove Room
Turtle Cove RoomKent 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."
Jennifer M.
$171 nightly
The price is $186
Nov 9 - Nov 10
Total with taxes and fees
7. Wren Retweet- Country Estate in Center of C’Town
Wren Retweet- Country Estate in Center of C’TownChestertown
10.0 out of 10, Exceptional, (76 reviews)
"Perfect location for exploring the cutest town. "
Mandy D.
$428 nightly
The price is $444
Nov 9 - Nov 10
Total with taxes and fees
8. Beachcomber Suite
Beachcomber SuiteKent 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...
Lisa E.
$183 nightly
The price is $199
Nov 9 - Nov 10
Total with taxes and fees
9. Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Cozy 1-bedroom in-law suite in lovely Chestertown with ACChestertown
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...
Miriam G.
$253 nightly
The price is $268
Nov 15 - Nov 16
Total with taxes and fees
10. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVELAberdeen
10.0 out of 10, Exceptional, (13 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."
Andy W.
$134 nightly
The price is $142
Nov 11 - Nov 12
Total with taxes and fees
11. Bay Sunsets for Two • Rooftop Fire Pit
Bay Sunsets for Two • Rooftop Fire PitPasadena
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"
Charles W.
$399 nightly
The price is $454
Nov 15 - Nov 16
Total with taxes and fees
12. Cass-N-Reel Luxury Houseboat
Cass-N-Reel Luxury HouseboatGrasonville
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."
Yamilet
$226 nightly
The price is $250
Nov 12 - Nov 13
Total with taxes and fees
13. B’more Restful. Comfortable Townhome -Easy access to everywhere
B’more Restful. Comfortable Townhome -Easy access to everywhereDundalk
10.0 out of 10, Exceptional, (18 reviews)
"very wonderful home and very quite area "
alan d.
$263 nightly
The price is $304
Nov 9 - Nov 10
Total with taxes and fees
14. Family Retreat at Lansdowne Manor
Family Retreat at Lansdowne ManorCentreville
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! "
Emily C.
$252 nightly
The price is $280
Nov 9 - Nov 10
Total with taxes and fees
15. Pool Loft Suite | Bay Access & Beach Passes
Pool Loft Suite | Bay Access & Beach PassesCape 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."
Ana S.
$395 nightly
The price is $450
Nov 9 - Nov 10
Total with taxes and fees
16. Chesapeake Cottages- 2 Quaint Waterfront Retreats
Chesapeake Cottages- 2 Quaint Waterfront RetreatsPasadena
9.6 out of 10, Exceptional, (24 reviews)
"Excellent Property"
Buu T.
$528 nightly
The price is $602
Nov 9 - Nov 10
Total with taxes and fees
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!"
Antonia P.
$400 nightly
The price is $456
Nov 15 - Nov 16
Total with taxes and fees
18. Family Friendly Cozy 3 Bedroom Duplex
Family Friendly Cozy 3 Bedroom DuplexGrasonville
$285 nightly
The price is $302
Nov 10 - Nov 11
Total with taxes and fees
19. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 MinCape Saint Claire
9.2 out of 10, Wonderful, (19 reviews)
"Quiet neighborhood, worked well for our group of 8."
Jennifer H.
$495 nightly
The price is $564
Nov 9 - Nov 10
Total with taxes and fees
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
Comfort Inn & Suites Chestertown
Comfort Inn & Suites ChestertownChestertown
10/10 Excellent
Inside the building it was clean, quiet and nice. In the back parking lot, it was very dirty. The grounds surrounding the lot was littered with trash and debris. One person looked to be sleeping in his car. I did appreciate the very bright lighting in that lot. A small clean up of the back lot would make a big difference in first impressions!!
Laura
