Fairlee Vacation Rentals

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Check prices for these dates

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Dec 6 - Dec 7
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Dec 7 - Dec 8
Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21

Vacation Rentals in Fairlee

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

Vacation Home in Pasadena

9.4 out of 10, Exceptional, (89)
"This property was a great place for a family to all relax together, play games, and enjoy the water!"
United States
Armando V.
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
6 bedrooms, iron/ironing board, WiFi, bed sheets
Luxury Waterfront Home Built for Entertaining!

Vacation Home in Abingdon

8.4 out of 10, Very Good, (6)
"Quite lovely house with a gorgeous view over the water. It is definitely a good spot to stay with a large family or friends for a few days with plenty to do (relaxing on the dock, play games inside, not too far from Baltimore and other nice towns, etc). The host was great and very communicative as well.The only downsides were details around cleanliness and the check-out procedures. The house itself was overall fine, but there dishes left in the dishwasher that we had to put away, the bottom...
United States
Benjamin J.
The price is ￥76,789
￥128,919 total
includes taxes & fees
Dec 9 - Dec 10
Luxury Waterfront Home Built for Entertaining!
Marina
Cass-N-Reel Luxury Houseboat

Houseboat in Grasonville

10.0 out of 10, Exceptional, (47)
"Amazing views! Location is great, restaurants at walking distance, great bicicle trail, highly recommended!"
United States
Oliver C.
Cass-N-Reel Luxury Houseboat
Interior
200 steps to the beach!

Vacation Home in Rock Hall

10.0 out of 10, Exceptional, (93)
"Beautiful, comfortable home in a great location. "
United States
Stephanie C.
200 steps to the beach!
Dining
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Villa in Rock Hall

9.8 out of 10, Exceptional, (40)
"Ashleigh was amazing as a host, got right back to us on all questions and needs. "
United States
Tim B.
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Property grounds
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Cottage in Pasadena

9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
The price is ￥55,847
￥103,103 total
includes taxes & fees
Dec 8 - Dec 9
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Outdoor dining
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Vacation Home in stevensville

10.0 out of 10, Exceptional, (197)
"This home was the perfect get-away for a group of friends!The accommodations were wonderful and the host went out of their way to ensure our stay was full of fun activities."
United States
David N.
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Outdoor dining
BAYSIDE BUNGALOW

Vacation Home in Rock Hall

10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is ￥31,066
￥46,925 total
includes taxes & fees
Jan 1 - Jan 2, 2026
BAYSIDE BUNGALOW
Property grounds
Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit

Vacation Home in Grasonville

10.0 out of 10, Exceptional, (24)
"Place was fantastic!"
United States
larry
Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit
Smart TV, books
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Cottage in Earleville

9.8 out of 10, Exceptional, (59)
"Lovely cottage, well-equipped, immaculately clean. "
United States
Mary
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Indoor pool
Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach

Villa in White Marsh

10.0 out of 10, Exceptional, (17)
"Beautiful views and equipped with everything you could ever want! They were even kind of enough to build us a fire for smores. "
United States
Nusayba H.
Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach
Fridge, microwave, oven, stovetop
Waterfront CHeerful 2 with Private Pier

Vacation Home in Gibson Island

9.8 out of 10, Exceptional, (19)
"Great place we stayed while visiting family in the area. Great to decompress from all the chaos."
United States
Karolyn M.
Waterfront CHeerful 2 with Private Pier
Terrace/patio
Close to Hospital & White Marsh! Rosedale Townhome

Vacation Home in Nottingham

2.0 star property
The price is ￥26,372
￥82,178 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Close to Hospital & White Marsh! Rosedale Townhome
Property grounds
First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown

9.6 out of 10, Exceptional, (107)
"Amazing and neat and very private "
United States
Alexander M.
The price is ￥15,358
￥24,641 total
includes taxes & fees
Dec 9 - Dec 10
First Floor Studio Apartment in Historic Chestertown
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Vacation Home in Cape Saint Claire

10.0 out of 10, Exceptional, (39)
"Fabulous place. We’ll be booking again next year. "
United States
Steve R.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop
Waterfront! Private Dock, Boat Tie-Up & Near Town

Vacation Home in Rock Hall

10.0 out of 10, Exceptional, (2)
"A beautiful spot."
United States
Laura S.
Waterfront! Private Dock, Boat Tie-Up & Near Town
Dining
Cass-Away Luxury Houseboat

Houseboat in Grasonville

10.0 out of 10, Exceptional, (104)
"What a unique experience to stay on a houseboat. Such a fun locale & comfortable accommodations. "
United States
Robin L.
Cass-Away Luxury Houseboat
Marina
Waterfront Oasis w/ Private Dock, 3BR/2BA

Vacation Home in Middle River

9.4 out of 10, Exceptional, (39)
"Perfect place, close to the park and the most amazing sunset "
United States
Nicoleta E.
Waterfront Oasis w/ Private Dock, 3BR/2BA
Beach
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Apartment in Rock Hall

10.0 out of 10, Exceptional, (17)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
The price is ￥19,236
￥45,226 total
includes taxes & fees
Dec 9 - Dec 10
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Property grounds
Circa 1900 Home in the Heart of Historic Downtown Chestertown

Vacation Home in Chestertown

10.0 out of 10, Exceptional, (76)
"Great house, will stay again in the future. "
United States
Gary N.
Circa 1900 Home in the Heart of Historic Downtown Chestertown
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

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

10/10 Excellent
"Good stay "
D 3-night trip
Posted 2 days ago
Quality Inn & Suites Bel Air I-95 Exit 77A

Find out more about Fairlee

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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?

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !: Visitors like this Fairlee vacation home rental. It is located on the beach and has a fireplace, a patio, and air-conditioning 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. You can relax into your vacation 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 Hazel Miner Monument, or get out into nature at a spot like Betterton Beach. Washington College and Chestertown Historic District 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.