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Fairlee Vacation Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

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
9.8 out of 10, Exceptional, (23 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is SAR 255
SAR 469 total
includes taxes & fees
29 Jun - 30 Jun
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, (113 reviews)
"Every thing was great"
United States
lesia k.
The price is SAR 372
SAR 596 total
includes taxes & fees
23 Jun - 24 Jun
First Floor Studio Apartment in Historic Chestertown
Property grounds

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is SAR 591
SAR 1,594 total
includes taxes & fees
23 Jun - 24 Jun
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
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, (23 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is SAR 442
SAR 1,057 total
includes taxes & fees
23 Jun - 24 Jun
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
House (3 Bedrooms) | Interior

2 Mi to Apg: Edgewood Family Home w/ Fenced Yard

2 Mi to Apg: Edgewood Family Home w/ Fenced Yard
3.0 star property
Edgewood
The price is SAR 413
SAR 1,642 total
includes taxes & fees
25 Jun - 26 Jun
2 Mi to Apg: Edgewood Family Home w/ Fenced Yard
WiFi, bed sheets

Turtle Cove Room

Turtle Cove Room
Kent County
The price is SAR 527
SAR 654 total
includes taxes & fees
6 Jul - 7 Jul
Turtle Cove Room
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (56 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is SAR 751
SAR 1,138 total
includes taxes & fees
23 Jun - 24 Jun
BAYSIDE BUNGALOW
Terrace/patio

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
10.0 out of 10, Exceptional, (1 review)
"Booked this property as a last minute, overnight getaway for myself and it was fantastic! The apartment, grounds and hot tub was squeaky clean. Kitchen was clean and stocked with utensils and even had a coffee bar, different tea packets and a snack basket. Bathroom was fully stocked with towels, basic toiletries and everything I needed. Bed was comfortable and closets had extra blankets if needed. Inside and outside patio furniture was comfy. I loved watching the sunset from the hot tub! Also...
United States
Kayla K.
The price is SAR 608
SAR 724 total
includes taxes & fees
23 Jun - 24 Jun
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Property grounds

Beachcomber Suite

Beachcomber Suite
Kent County
The price is SAR 547
SAR 676 total
includes taxes & fees
13 Jul - 14 Jul
Beachcomber Suite
Beach nearby

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is SAR 845
SAR 1,421 total
includes taxes & fees
28 Jun - 29 Jun
Waterfront Retreat with Private Dock and Beach
Fridge, microwave, oven, stovetop

Gorgeous 3-bedroom townhome with AC in friendly Dundalk

Gorgeous 3-bedroom townhome with AC in friendly Dundalk
Dundalk
6.0 out of 10, (3 reviews)
"For an older property, the kitchen upgrade was nice, I like the basement level and the double queen bunk beds. The type of furniture, it can easily sleep the number of people I requested. I only had 3 adults and 1 child, which was more than enough space for the price."
United States
Linda T.
The price is SAR 422
SAR 804 total
includes taxes & fees
30 Jun - 1 Jul
Gorgeous 3-bedroom townhome with AC in friendly Dundalk
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, (14 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is SAR 938
SAR 1,572 total
includes taxes & fees
23 Jun - 24 Jun
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Smart TV, books

Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
9.8 out of 10, Exceptional, (29 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
The price is SAR 938
SAR 1,446 total
includes taxes & fees
25 Jun - 26 Jun
Newly restored apartment in the heart of Chestertown
Smart TV

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is SAR 657
SAR 1,365 total
includes taxes & fees
29 Jun - 30 Jun
Bayside Cottage steps from Rock Hall Harbor
Exterior detail

2 Mi to APG: Edgewood Family Home w/ Fenced Yard

2 Mi to APG: Edgewood Family Home w/ Fenced Yard
Edgewood
4.0 out of 10, (1 review)
"The house was okay. Definitely wasnt cleaned thoroughly as there was still food stains in the fridge and peices of food in the butter tray inside the fridge. The stove would not work until i set the time to the correct time so that was a bit of a question mark as to why that was. There was ants all over inside the house which personally was very disgusting. Both me and my son woke up with ants crawling on us in both the master bedroom and back bedroom. So that is something that should be...
United States
Sean G.
The price is SAR 372
SAR 1,654 total
includes taxes & fees
25 Jun - 26 Jun
2 Mi to APG: Edgewood Family Home w/ Fenced Yard
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 SAR 1,351
SAR 2,495 total
includes taxes & fees
29 Jun - 30 Jun
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Dining

Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!
Abingdon
9.2 out of 10, Wonderful, (11 reviews)
"Very clean, spacious and quiet!!!!! Beautiful home! "
United States
Jennifer M.
The price is SAR 3,003
SAR 4,544 total
includes taxes & fees
27 Jun - 28 Jun
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.
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Top Fairlee Hotel Reviews

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"Wonderful facility. Enjoyed the on site amenities. The garden was an interesting twist.Stayed in the Barn, a little tight for two people but well designed space. I would recommend if in the area."
Amanda 2-night trip
Posted 5 hours ago
The Inn at Chesapeake Bay Beach Club

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 Kinnairds Point Drive. 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.