Fairlee Holiday Rentals

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Our top choices for Fairlee holiday rentals

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
9.6 out of 10, Exceptional, (19 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is AU$188
includes taxes & fees
5 Feb - 6 Feb
Guest Suite for up to 2 in a Victorian on the Chester River

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is AU$238
includes taxes & fees
29 Jan - 30 Jan
First Floor Studio Apartment in Historic 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, (17 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is AU$426
includes taxes & fees
23 Jan - 24 Jan
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (52 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is AU$446
includes taxes & fees
24 Jan - 25 Jan
BAYSIDE BUNGALOW

Grandma’s Cottage will wrap around you like a warm hug

Grandma’s Cottage will wrap around you like a warm hug
Betterton
The price is AU$609
includes taxes & fees
3 Feb - 4 Feb
Grandma’s Cottage will wrap around you like a warm hug

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, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is AU$611
includes taxes & fees
26 Jan - 27 Jan
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"The apartment, including kitchen and bathroom, was very clean. Plenty of linens available for use. Perfect spot for fishing off of their dock. Very pleased with our reservation. "
United States
Debbie S.
The price is AU$464
includes taxes & fees
27 Jan - 28 Jan
Waterfront Retreat with Private Dock and Beach

Close to Hospital & White Marsh! Rosedale Townhome

Close to Hospital & White Marsh! Rosedale Townhome
3.0 star property
Nottingham
The price is AU$758
includes taxes & fees
25 Jan - 26 Jan
Close to Hospital & White Marsh! Rosedale Townhome

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is AU$615
includes taxes & fees
28 Jan - 29 Jan
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!
Abingdon
8.8 out of 10, Excellent, (8 reviews)
"We had such a wonderful stay! The house was spotless, comfortable, and beautifully maintained. The surrounding area was peaceful and welcoming, and perfect for a relaxing weekend. Highly recommend!"
United States
Oluwaseyi E.
The price is AU$1,301
includes taxes & fees
24 Jan - 25 Jan
Luxury Waterfront Home Built for Entertaining!

High Tide Haven Suite

High Tide Haven Suite
Kent County
The price is AU$302
includes taxes & fees
23 Jan - 24 Jan
High Tide Haven Suite

Close to Hospital & White Marsh! Rosedale Townhome

Close to Hospital & White Marsh! Rosedale Townhome
2.0 star property
Nottingham
2.0 out of 10, (1 review)
"House was poorly maintained. Bathrooms, dishes, kitchen, floors, refrigerator were dirty. Lac of furniture, etc. We left the 2nd day from an 8 day stay and Vrbo CS and Envolve did nothing to at least reimburse the remaining of the stay, regardless the emails and picture sent. Never again. "
United States
Christopher T.
The price is AU$755
includes taxes & fees
26 Jan - 27 Jan
Close to Hospital & White Marsh! Rosedale Townhome
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

Find out more about Fairlee

Everything you need to know about Fairlee holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Fairlee holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Fairlee holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Fairlee holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Fairlee. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Fairlee holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Fairlee holiday rentals we have selected for you start as low as AU$446 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Fairlee rentals

At Expedia, we put the best Fairlee holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Fairlee rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Fairlee holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Fairlee. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Fairlee?

Yes, there are holiday rentals close to the most popular sights in Fairlee, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Fairlee has to offer?

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !: This holiday home rental outside of Fairlee 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 that you can cook with friends or family. You can relax into your holiday 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 Ferry Park. Washington College and Chestertown Historic District are a couple of places you'll find in the wider area.

What’s a holiday rental in Fairlee like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Fairlee. Holiday rentals offer extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for family gatherings.