Fairlee Vacation Rentals

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Our top choices for Fairlee vacation rentals

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"Every thing was great"
United States
lesia k.
The price is CA $136
CA $219 total
includes taxes & fees
Apr 20 - Apr 21
First Floor Studio Apartment in Historic Chestertown

Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.6 out of 10, Exceptional, (20 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is CA $94
CA $172 total
includes taxes & fees
Apr 16 - Apr 17
Guest Suite for up to 2 in a Victorian on the Chester River

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 reviews)
"Great overnight stay for a wedding nearby. Would highly recommend!"
United States
Kevin F.
The price is CA $344
CA $578 total
includes taxes & fees
Apr 16 - Apr 17
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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, (18 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is CA $162
CA $393 total
includes taxes & fees
Apr 16 - Apr 17
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
United States
Dorothy R.
The price is CA $241
CA $499 total
includes taxes & fees
Apr 17 - Apr 18
Bayside Cottage steps from Rock Hall Harbor

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is CA $241
CA $620 total
includes taxes & fees
Apr 27 - Apr 28
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (52 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is CA $275
CA $417 total
includes taxes & fees
May 4 - May 5
BAYSIDE BUNGALOW

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"The apartment, including kitchen and bathroom, was very clean. Plenty of linens available for use. Perfect spot for fishing off of their dock. Very pleased with our reservation. "
United States
Debbie S.
Waterfront Retreat with Private Dock and Beach

High Tide Haven Suite

High Tide Haven Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"The suite was really nice and extremely clean. Comfy, memory foam bed. Excellent shower with great water pressure. The ambiance in the room is serene and beachy making for a wonderful escape. Absolutely loved their screened in porch and view from the back deck. The hosts were very nice, had great communication and served the most delicious bagels. We left our phone charger there and they promptly called us in time to turn around and get it. Highly recommend this location and will stay there...
United States
Joell V.
The price is CA $181
CA $226 total
includes taxes & fees
Apr 20 - Apr 21
High Tide Haven Suite

Serenity on the Cove

Serenity on the Cove
Dundalk
9.8 out of 10, Exceptional, (9 reviews)
"Great stay - would stay again "
United States
Anonymous traveller
The price is CA $248
CA $1,582 total
includes taxes & fees
Apr 19 - Apr 20
Serenity on the Cove

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (22 reviews)
"Excellent Property"
United States
Buu T.
The price is CA $496
CA $915 total
includes taxes & fees
Apr 20 - Apr 21
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Grandma’s Cottage will wrap around you like a warm hug

Grandma’s Cottage will wrap around you like a warm hug
Betterton
The price is CA $310
CA $581 total
includes taxes & fees
Apr 18 - Apr 19
Grandma’s Cottage will wrap around you like a warm hug

Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!
Abingdon
9.0 out of 10, Wonderful, (9 reviews)
"Excellent communication with host, we had everything we needed"
United States
Kelly W.
The price is CA $1,101
CA $1,655 total
includes taxes & fees
Apr 16 - Apr 17
Luxury Waterfront Home Built for Entertaining!

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 $161
CA $527 total
includes taxes & fees
Apr 18 - Apr 19
Abingdon Haven Hideaway
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 Fairlee Hotel Reviews

Find out more about Fairlee

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 Fairlee. 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 Fairlee?

Yes, we give you a choice of vacation rentals near top sights in Fairlee, or you can choose a secluded option if you're looking for a relaxing stay.

What's the top vacation rental that Fairlee has to offer?

240' Private Beachfront @Kent Island Love Point - Great for Families: Visitors like this Fairlee vacation home rental. It is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Fairlee?

Explore the area and family-friendly sights such as Crumpton Auction, or get out into nature at a spot like Betterton Beach. Washington College and River Arts Chestertown are a couple of places you'll find in the larger area.

What’s a vacation rental in Fairlee like?

Vacation rentals are privately owned properties where you can stay for several days or longer in Fairlee. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for family gatherings.