Fairlee Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Fairlee vacation rentals

Exterior

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)
"Wonderful property. Extremely clean and comfortable. Everything was seamless, except for losing our key, which was of course 100% our fault, but Teddi was very kind about the situation. Property was lovely, including the sitting room. "
United States
Carla B.
The price is ￥10,858
￥19,972 total
includes taxes & fees
Apr 1 - Apr 2
Guest Suite for up to 2 in a Victorian on the Chester River
Property grounds

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 ￥15,807
￥25,362 total
includes taxes & fees
Mar 31 - Apr 1
First Floor Studio Apartment in Historic Chestertown
Beach

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 ￥18,885
￥45,804 total
includes taxes & fees
Mar 29 - Mar 30
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Dining

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)
"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. "
United States
Joe C.
The price is ￥39,918
￥66,854 total
includes taxes & fees
Apr 3 - Apr 4
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Terrace/patio

High Tide Haven Suite

High Tide Haven Suite
Kent County
The price is ￥27,663
￥31,878 total
includes taxes & fees
Mar 31 - Apr 1
High Tide Haven Suite
Beach

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.
The price is ￥27,942
￥48,032 total
includes taxes & fees
Apr 20 - Apr 21
Waterfront Retreat with Private Dock and Beach
Smart TV

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 ￥27,942
￥57,037 total
includes taxes & fees
Apr 20 - Apr 21
Bayside Cottage steps from Rock Hall Harbor
Fridge, microwave, oven, stovetop

Welcome to the secluded waterfront oasis

Welcome to the secluded waterfront oasis
Millington
Welcome to the secluded waterfront oasis
Property grounds

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is ￥28,784
￥73,018 total
includes taxes & fees
Apr 5 - Apr 6
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Dining

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 ￥35,926
￥67,023 total
includes taxes & fees
Mar 29 - Mar 30
Grandma’s Cottage will wrap around you like a warm hug
Interior

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 ￥18,756
￥61,684 total
includes taxes & fees
Apr 5 - Apr 6
Abingdon Haven Hideaway
Exterior detail

Pool + Hot Tub + Pickleball | Waterfront

Pool + Hot Tub + Pickleball | Waterfront
Church Hill
The price is ￥55,628
￥146,561 total
includes taxes & fees
Mar 30 - Mar 31
Pool + Hot Tub + Pickleball | Waterfront
Property grounds

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 ￥57,481
￥106,120 total
includes taxes & fees
Apr 2 - Apr 3
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Dining

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 ￥127,736
￥193,284 total
includes taxes & fees
Apr 14 - Apr 15
Luxury Waterfront Home Built for Entertaining!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Fairlee Hotel Reviews

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

10/10 Excellent
"Yes, I did not expect a full breakfast, and parking was safe"
Barbara 3-night trip
Posted 17 hours ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

Find out more about Fairlee

Search for holiday rentals in Fairlee on Expedia! You can easily find your home rentals, villas, holiday apartments in Fairlee using one of the methods below:

  • View our selection of featured holiday rentals in Fairlee
  • Use the map to find apartments and other holiday homes in the Fairlee neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Fairlee while they last

Look no further and take a look at our great range of rental properties in Fairlee!

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?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: Visitors like this Fairlee vacation home rental. It 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’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.