Fairlee Vacation Rentals

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Next weekend
Aug 1 - Aug 3
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Aug 8 - Aug 10
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Aug 22 - Aug 24
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Sep 19 - Sep 21

Browse Select Fairlee Vacation Homes

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Enjoy a meal with a view of the ocean from this dining area with large windows.

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

10.0 out of 10, Exceptional, (6)
"Relaxing and stunning location. Beautiful bay front property with stunning views of the bay. If you are looking for a quiet and peaceful getaway that involves wildlife sightings this is the perfect spot. Well equipped and roomy rental. Very clean too. "
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
BAYSIDE BUNGALOW
Relax in a serene sauna with a wooden bench and natural ambiance.

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (42)
"Beautiful, cozy cottage. So peaceful and pretty. Owners are on site and are great people. We have stayed here several times and look forward to coming back soon."
The price is CA $274
CA $413 total
includes taxes & fees
Jul 24 - Jul 25
BAYSIDE BUNGALOW
Peaceful Queenstown Home w/ Deck & Grill!
Enjoy cooking in this well-equipped kitchen with a central island, ample counter space, and appliances.

Peaceful Queenstown Home w/ Deck & Grill!

9.6 out of 10, Exceptional, (9)
"Very cozy, a very quiet home"
Peaceful Queenstown Home w/ Deck & Grill!
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Relax in this serene outdoor seating area with a glass-top table and wicker chairs, surrounded by a wooden deck and large windows offering views of the surrounding landscape.

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

10.0 out of 10, Exceptional, (188)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Enjoy a serene beach experience with access to the ocean via the public pier.

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

9.6 out of 10, Exceptional, (41)
"This is the second time my husband and I have stayed here. Despite a mixed bag of weather ranging from snow, rain, winds, and sunshine, the visit did not disappoint. We were still able to walk on the beach, view the resident bald eagle, immerse ourselves in the ever changing water views and visit surrounding towns.The house was warm and welcoming."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Relax in a serene hot tub under a covered pergola with a breathtaking view of the surrounding landscape.

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (6)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is CA $270
CA $609 total
includes taxes & fees
Jul 23 - Jul 24
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD
Guests can enjoy a patio with a table and chairs, surrounded by a wooden fence.

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

10.0 out of 10, Exceptional, (7)
"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
Grasonville Home w/ Private Pool on the Water
Relax by the serene pool overlooking the lake, surrounded by a lawn and shaded by a large tree.

Grasonville Home w/ Private Pool on the Water

10.0 out of 10, Exceptional, (21)
"Location was great for our stay"
Grasonville Home w/ Private Pool on the Water
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 8 with pond view!
Relax by the tranquil lake surrounded by tall pine trees, with a fire pit and seating area for a peaceful retreat.

Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 8 with pond view!

10.0 out of 10, Exceptional, (24)
"Good location."
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 8 with pond view!
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Stylish single-story home with a symmetrical facade, featuring evenly spaced windows and a central entrance.

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!"
The price is CA $342
CA $580 total
includes taxes & fees
Jul 23 - Jul 24
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Stay in the landmark Lighthouse!
Enjoy serene views of the calm body of water from the breakwater.

Stay in the landmark Lighthouse!

10.0 out of 10, Exceptional, (102)
"Great views, unique living space and all the amenities. Really enjoyed our stay!"
Stay in the landmark Lighthouse!
Beautiful home & short walk to beach, restaurants, and marinas in Rock Hall, MD
Enjoy a serene beach experience with a natural barrier of rocks separating the calm sea from the sandy shore.

Beautiful home & short walk to beach, restaurants, and marinas in Rock Hall, MD

10.0 out of 10, Exceptional, (19)
"We really enjoyed our stay in Rock Hall! Perfect house in a great location."
Beautiful home & short walk to beach, restaurants, and marinas in Rock Hall, MD
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Stroll through the serene garden, surrounded by vibrant flowers and a charming birdcage.

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (72)
"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
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Enjoy meals in the spacious kitchen and dining area with a central island and large window offering a view of the outdoors.

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

10.0 out of 10, Exceptional, (30)
"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Property grounds

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

9.4 out of 10, Exceptional, (88)
"What a wonderful vacation we had everything you want is there. All you have to bring is food . The trampoline will keep everyone occupied for hours. Looking forward to staying there in the future."
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Gorgeous Creek Side Ranch-Style Estate With Dock
Enjoy cooking in this well-equipped kitchen with a stainless steel refrigerator, oven, and wine cooler.

Gorgeous Creek Side Ranch-Style Estate With Dock

9.8 out of 10, Exceptional, (8)
"We were in town for a family wedding and throughly enjoyed our stay at this beautiful house. The property is gorgeous and the house has everything you need to make your stay enjoyable. We will definitely be back when visiting family in the area. "
The price is CA $276
CA $1,114 total
includes taxes & fees
Jul 24 - Jul 25
Gorgeous Creek Side Ranch-Style Estate With Dock
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Enjoy a meal with a view from the kitchen's glass doors, which lead to a patio with a deck and seating area overlooking a serene landscape.

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (53)
"Great location with a great view."
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Sprawling Waterfront Home with views, Dock and In-Home Theatre
Relax on the deck with Adirondack chairs and a small table, surrounded by mature trees and a serene body of water.

Sprawling Waterfront Home with views, Dock and In-Home Theatre

10.0 out of 10, Exceptional, (1)
Sprawling Waterfront Home with views, Dock and In-Home Theatre
Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.
Mooring cleats line the tranquil marina, where boats can be docked.

Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.

10.0 out of 10, Exceptional, (7)
"Property was extremely well kempt. It was beautiful. We enjoyed ourselves there and would recommend it to others."
Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Escape to a charming cottage surrounded by lush greenery and trees, with a cozy porch and a brick chimney.

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

9.8 out of 10, Exceptional, (82)
"Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts."
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
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

Holiday Inn Express White Marsh by IHG

Holiday Inn Express White Marsh by IHG

10/10 Excellent
"Clean room, quiet environment "
DOMINIC 2-night trip
Posted 2 days ago
Holiday Inn Express White Marsh by IHG