Default HTG hotel image

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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Fairlee vacation rentals

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

1. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (130 reviews)
"This property is delightful. It's very "beachy" and relaxing. There are lots of thoughtful amenities which made our stay smooth. The only thing I would mention is that the property is reached by a set of six stair steps, even though strictly speaking it is on the first floor of the house. That wasn't a problem for us. Other than that, we can highly recommend it. We thoroughly enjoyed our stay here. (My husband wants me to mention that he loved the bed and slept very well.)"
United States
Charr
The price is ￥15,627
￥25,073 total
includes taxes & fees
Oct 12 - Oct 13
First Floor Studio Apartment in Historic Chestertown
A spacious living area with a dining table, sofa, and a kitchen in the background.

2. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (33 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
The price is ￥35,516
￥55,585 total
includes taxes & fees
Oct 14 - Oct 15
Newly restored apartment in the heart of Chestertown
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

3. 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, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is ￥18,595
￥44,767 total
includes taxes & fees
Oct 7 - Oct 8
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

4. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is ￥28,981
￥43,247 total
includes taxes & fees
Oct 8 - Oct 9
Secluded Cottage in Middle of Chestertown
A building with a gabled roof and a circular vent on the roof.

5. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (66 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is ￥31,570
￥49,827 total
includes taxes & fees
Oct 7 - Oct 8
BAYSIDE BUNGALOW
A hallway with wooden flooring, a door on the right, and a window at the end.

6. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is ￥48,075
￥75,969 total
includes taxes & fees
Oct 27 - Oct 28
Wren Retweet- Country Estate in Center of C’Town
A deck with outdoor furniture, a potted plant, and a house in the background.

7. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
The price is ￥34,727
￥48,690 total
includes taxes & fees
Oct 12 - Oct 13
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A bedroom with a bed, a dresser, a mirror, and a door.

8. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
Betterton
The price is ￥28,282
￥56,605 total
includes taxes & fees
Oct 18 - Oct 19
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
A modern kitchen with white cabinetry, stainless steel appliances, and a marble countertop.

9. Private 2 story waterfront entire home w/ dedicated pier located on Sue Creek!

Private 2 story waterfront entire home w/ dedicated pier located on Sue Creek!
Essex
The price is ￥49,528
￥87,300 total
includes taxes & fees
Oct 16 - Oct 17
Private 2 story waterfront entire home w/ dedicated pier located on Sue Creek!
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

10. 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, (11 reviews)
"The host was incredibly friendly and communicative. The place was a lot bigger than I expected, and it was beautiful to sit out by the fire pit and look at the river nearby. And, she left us snacks and smores for the stay! A nice quiet spot to spend a night."
United States
Matthew
The price is ￥19,739
￥24,271 total
includes taxes & fees
Nov 2 - Nov 3
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

11. 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, (29 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 ￥10,734
￥19,744 total
includes taxes & fees
Oct 7 - Oct 8
Guest Suite for up to 2 in a Victorian on the Chester River
A modern kitchen with stainless steel appliances, white cabinetry, and a brick backsplash.

12. B’more Restful. Comfortable Townhome -Easy access to everywhere

B’more Restful. Comfortable Townhome -Easy access to everywhere
Dundalk
10.0 out of 10, Exceptional, (15 reviews)
"very wonderful home and very quite area "
United States
alan d.
The price is ￥31,412
￥54,330 total
includes taxes & fees
Oct 19 - Oct 20
B’more Restful. Comfortable Townhome -Easy access to everywhere
A modern kitchen with dark cabinets, a white countertop, and a large window.

13. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (51 reviews)
"Had a great time, great property and great location."
United States
Danny B.
Cass-N-Reel Luxury Houseboat
A kitchen with wooden cabinets, a dining table, and a refrigerator.

14. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (13 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
The price is ￥36,290
￥45,302 total
includes taxes & fees
Oct 12 - Oct 13
Family Retreat at Lansdowne Manor
A sunset view from a balcony with a glass-top table and a fire feature, overlooking the sea.

15. FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
10.0 out of 10, Exceptional, (2 reviews)
"FLOHOM 14 did not disappoint!!! This was my first stay on a houseboat. Now I know why babies fall asleep when rocked. The boat is beautifully appointed & well equipped. Bring a good book. I’m already missing it!!!"
United States
Maria D.
The price is ￥27,026
￥69,333 total
includes taxes & fees
Oct 8 - Oct 9
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
A narrow hallway with a kitchen area on one side, featuring a microwave, oven, and cabinets. There are three black bar stools along the hallway, and a potted plant on the counter.

16. 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 ￥18,468
￥59,900 total
includes taxes & fees
Oct 8 - Oct 9
Abingdon Haven Hideaway
A wooden dock with Adirondack chairs and a ladder, overlooking a calm body of water with a distant shoreline.

17. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (24 reviews)
"Excellent Property"
United States
Buu T.
The price is ￥56,826
￥104,910 total
includes taxes & fees
Oct 12 - Oct 13
Chesapeake Cottages- 2 Quaint Waterfront Retreats
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

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"We always stay here when we go to Baltimore, we love it!"
Tina 1-night trip
Posted 1 hour ago
Hilton Garden Inn Baltimore/White Marsh

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.