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Our top choices for Fairlee vacation homes
HGTV quality, private guest suite, country getaway with hot tub & fire pit
HGTV quality, private guest suite, country getaway with hot tub & fire pitCentreville
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
Renee P.
$414 nightly
The price is $439
Dec 15 - Dec 16
Total with taxes and fees
$193 nightly
The price is $200
Dec 14 - Dec 15
Total with taxes and fees
Chesapeake Bay Harbor View in a central location to events/restaurants
Chesapeake Bay Harbor View in a central location to events/restaurantsRock Hall
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
Todd W.
$257 nightly
The price is $272
Dec 14 - Dec 15
Total with taxes and fees
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
Modern and Cozy Home in Bel Air with a Home Office and FireplaceBel Air
10.0 out of 10, Exceptional, (5)
"I appreciated how clean and pleasant it smelled! Then it was a beautiful location with lots of places to eat nearby. My only improvement would have been window curtains, especially in the master bath. "
Leah M.
New! Stylish downtown home w/awesome outdoor area!
New! Stylish downtown home w/awesome outdoor area!Stevensville
9.8 out of 10, Exceptional, (26)
"The house was spacious, clean, and in a great location. The owners were available, and easy to communicate with."
Marjorie N.
$475 nightly
The price is $503
Dec 25 - Dec 26
Total with taxes and fees
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, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
Joe C.
$394 nightly
The price is $418
Dec 15 - Dec 16
Total with taxes and fees
BAYSIDE BUNGALOW
BAYSIDE BUNGALOWRock Hall
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
Roger
$257 nightly
The price is $272
Jan 10 - Jan 11, 2026
Total with taxes and fees
Close to Hospital & White Marsh! Rosedale Townhome
Close to Hospital & White Marsh! Rosedale TownhomeNottingham
$459 nightly
The price is $526
Dec 14 - Dec 15
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.
Top Fairlee Hotel Reviews
Comfort Inn & Suites Chestertown
10/10 Excellent
Find out more about Fairlee
Fairlee Vacation Homes information
Number of reviews | 109 |
|---|---|
Accommodation | 143 Vacation Homes |
Lowest Price | $200 |
Highest Price | $831 |
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