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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Fairlee vacation rentals

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (118 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is CA $139
CA $224 total
includes taxes & fees
Jul 27 - Jul 28
First Floor Studio Apartment in Historic Chestertown

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 CA $96
CA $176 total
includes taxes & fees
Jul 27 - Jul 28
Guest Suite for up to 2 in a Victorian on the Chester River

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (59 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is CA $253
CA $393 total
includes taxes & fees
Aug 4 - Aug 5
BAYSIDE BUNGALOW

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)
"The house was lovely, very comfortable and hosts were very responsive! We will be back for another stay. "
United States
Diana S.
The price is CA $566
CA $832 total
includes taxes & fees
Aug 17 - Aug 18
Wren Retweet- Country Estate in Center of C’Town

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 CA $259
CA $399 total
includes taxes & fees
Aug 5 - Aug 6
Secluded Cottage in Middle of Chestertown

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, (26 reviews)
"Kitchen was fully stocked, apartment very clean, very nice host and parking was great"
United States
Tara K.
The price is CA $175
CA $415 total
includes taxes & fees
Jul 26 - Jul 27
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is CA $317
CA $527 total
includes taxes & fees
Jul 29 - Jul 30
Waterfront Retreat with Private Dock and Beach

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 CA $253
CA $521 total
includes taxes & fees
Jul 27 - Jul 28
Bayside Cottage steps from Rock Hall Harbor

Turtle Cove Room

Turtle Cove Room
Kent County
The price is CA $198
CA $245 total
includes taxes & fees
Jul 27 - Jul 28
Turtle Cove Room

Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
The price is CA $213
CA $262 total
includes taxes & fees
Aug 24 - Aug 25
Beachcomber Suite

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (23 reviews)
"Excellent Property"
United States
Buu T.
The price is CA $507
CA $936 total
includes taxes & fees
Jul 27 - Jul 28
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Gorgeous 3-bedroom townhome with AC in friendly Dundalk

Gorgeous 3-bedroom townhome with AC in friendly Dundalk
Dundalk
6.0 out of 10, (4 reviews)
"Overall you’re getting what you pay for. The downstairs toilet didn’t work and there weren’t any towels or lotion but the place was spacey and nice"
United States
Tobi A.
The price is CA $195
CA $367 total
includes taxes & fees
Aug 4 - Aug 5
Gorgeous 3-bedroom townhome with AC in friendly Dundalk

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, (15 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 CA $352
CA $594 total
includes taxes & fees
Jul 27 - Jul 28
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is CA $222
CA $601 total
includes taxes & fees
Jul 27 - Jul 28
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

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, (3 reviews)
"Beautiful location, nicely decorated. The host thought of everything you may need including a free snack basket, washer/dryer with detergent and dryer sheets, BBQ grill with utensils, board games and cards, kayaks and life vests, hot tub, firetable etc."
United States
Andy W.
The price is CA $253
CA $303 total
includes taxes & fees
Aug 4 - Aug 5
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

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 CA $165
CA $539 total
includes taxes & fees
Aug 4 - Aug 5
Abingdon Haven Hideaway
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Fairlee. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Stay in the landmark Lighthouse!: Visitors like this Fairlee vacation home rental. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

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.