Search Vacation Homes in Fairlee

Start date: Check-in selected.
End date: Check-out

Check prices for these dates

In two weeks
In two months
In three months
In four months

Vacation Homes in Fairlee

Our top choices for Fairlee vacation homes

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (32)
"We had 14 family members join us to celebrate my son’s graduation from the Naval Academy. The house is clean, the rooms were great, the property was beautiful, and it was close to USNA. Our family loved the open concept. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Waterfront Oasis w/ Private Dock, 3BR/2BA

9.4 out of 10, Exceptional, (35)
"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "
Waterfront Oasis w/ Private Dock, 3BR/2BA

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (73)
"House was in a great location and very well appointed. We had everything we needed. Would highly recommend."
Circa 1900 Home in the Heart of Historic Downtown Chestertown

River Front, Private Single Family Home

10.0 out of 10, Exceptional, (19)
"Host was very helpful and accommodating. Place was adorable with beautiful views, just as depicted. Had everything we needed and more! "
River Front, Private Single Family Home

Entire Townhouse in Rock Hall

10.0 out of 10, Exceptional, (31)
"Exactly what we expected. What wasn’t expected is how quiet and serene that entire town is. "
Entire Townhouse in Rock Hall

Luxury Waterfront Executive Family Home Annapolis with All Amenities

10.0 out of 10, Exceptional, (2)
"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "
Luxury Waterfront Executive Family Home Annapolis with All Amenities

Serene Waterfront Cottage with dock and gorgeous views.

9.6 out of 10, Exceptional, (38)
"Nice place with everything I could want. Would stay there again!"
Serene Waterfront Cottage with dock and gorgeous views.

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

10.0 out of 10, Exceptional, (6)
"The property is everything it claims to be & more. Awesome location on the bay. Great accommodations. So peaceful. We had a wonderful time. Would highly recommend! "
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

Beautiful, spacious, quiet waterfront house!

10.0 out of 10, Exceptional, (55)
"The place is fantastic. Beautiful views of the water, and the house is well-stocked with everything one might need for a relaxing, comfortable stay. Gordon is a very responsive and accommodating host. We had a lovely stay and would love to come back in the future."
Beautiful, spacious, quiet waterfront house!

Waterfront CHeerful 2 with Private Pier

9.6 out of 10, Exceptional, (15)
"We loved everything about this property: the renovations, the decor, and the location! Everything was well thought out. The beds were comfy. The location was quiet and peaceful with restaurants in close driving distance. "
Waterfront CHeerful 2 with Private Pier

Peaceful Queenstown Home w/ Deck & Grill!

9.6 out of 10, Exceptional, (9)
"Enjoyed this lovely and comfortable home tucked away in a private location close to amenities. "
Peaceful Queenstown Home w/ Deck & Grill!

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (190)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (47)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
$282 nightly
The price is $299
Sep 2 - Sep 3
Total with taxes and fees
BAYSIDE BUNGALOW

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (42)
"This is a jewel as it is private, peaceful with lovely setting."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

10.0 out of 10, Exceptional, (12)
"It was a great vacation, the house and grounds were spectacular, the amenities, pool, kayaks, were great, and host couldn’t have been more accommodating or approachable, highly recommend in the future, hope to go back"
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

9.6 out of 10, Exceptional, (21)
"a great place to unwind. "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD

10.0 out of 10, Exceptional, (9)
"This home was perfect for our 3 night stay. We came to spend time with our daughter who had moved to the area. The owners thought of everything and the little touches are what made this the perfect rental for our stay. Only downside was the weather did not allow us to enjoy the amazing views and cozy porches during our stay. Next time we visit with a group we will definitely stay here again!"
Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD

Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

10.0 out of 10, Exceptional, (23)
"Everything about this rental was perfect! "
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

Grasonville Home w/ Private Pool on the Water

10.0 out of 10, Exceptional, (23)
"Location was great for our stay"
Grasonville Home w/ Private Pool on the Water

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

9.8 out of 10, Exceptional, (11)
"Great overnight stay for a wedding nearby. Would highly recommend!"
$389 nightly
The price is $412
Sep 2 - Sep 3
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Fairlee Hotel Reviews

Find out more about Fairlee

Find out more about Fairlee

Fairlee Vacation Homes information

Number of reviews
Accommodation
149 Vacation Homes
Lowest Price
$299
Highest Price
$412

Explore a world of travel with Expedia

Explore a world of travel with Expedia