Fairlee holiday homes, MD, USA: holiday houses & more

Discover a selection of holiday rentals in Fairlee that are perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll have the best amenities for spending time at your home away from home, which might include a pool and a washer and dryer. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Fairlee

Showing deals for:18 Jul - 25 Jul

Outdoor seating area just off the kitchen.

Exceptional

(7 reviews)

Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

Rock Hall, MD

8% off

NZ$486 per night

includes taxes & fees

Exceptional

(7 reviews)

Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.

Rock Hall, MD

8% off

NZ$563 per night

includes taxes & fees

Master bedroom.. King-size bed and en-suite bathroom.

Exceptional

(10 reviews)

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

Chestertown, MD

12% off

NZ$386 per night

includes taxes & fees

Exceptional

(22 reviews)

Beautiful, spacious waterfront home, an easy walk to historic Chestertown

Chestertown, MD

8% off

NZ$2,086 per night

includes taxes & fees

20982 Bayside Ave, across from town dock, close to harbor and restaurants

Exceptional

(60 reviews)

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

Rock Hall, MD

8% off

NZ$554 per night

includes taxes & fees

Exceptional

(21 reviews)

Stunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler

Rock Hall, MD

8% off

NZ$2,354 per night

includes taxes & fees

Exceptional

(110 reviews)

Peaceful getaway convenient to local amenities including beach, boating & food

Rock Hall, MD

8% off

NZ$419 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Fairlee

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

Sleeps 12 · 4 bedrooms · 3 bathrooms

Baltimore Waterfront Home, fire-pit, picnic-shed,14 mi to Inner Harbor,sleeps 16

Sleeps 16 · 5 bedrooms · 5 bathrooms

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Book a holiday rental for your Fairlee getaway

Learn about the unique charm of Fairlee with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Fairlee

Are you searching for attractions to visit while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Fairlee has to offer. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

Queenstown Harbor Golf Club (16.1 mi / 25.9 km)
Queenstown Harbor Golf Links (16.1 mi / 25.9 km)
Cassinelli Winery and Vineyards (11.1 mi / 17.9 km)
Rocky Point Golf Course (13.1 mi / 21.1 km)
Hazel Miner Monument (13.5 mi / 21.7 km)
Crumpton Auction (13.9 mi / 22.3 km)

Exploring the natural landscape of Fairlee

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Fairlee is a great place to spend some time outside. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city centre:

Ferry Park (7.4 mi / 12 km)
Betterton Beach (11.8 mi / 19 km)
Miami Beach (12.1 mi / 19.4 km)
Rocky Point Park and Beach (12.6 mi / 20.3 km)
Eastern Neck National Wildlife Refuge (13.5 mi / 21.8 km)
Downs Park Dog Beach (15.9 mi / 25.5 km)

How to get to and around Fairlee

The closest airport is in Baltimore, MD (MTN-Martin State), located 15.2 mi (24.5 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Baltimore Washington International Airport (BWI), which is 26.8 mi (43.1 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Fairlee?

Houses are the most popular style of holiday home in Fairlee, according to our data. Even if you have a different idea about what you want, Bookabach has properties in all shapes and sizes. Look over our options to find your perfect pad.

How much does it cost to rent a holiday home in Fairlee?

Season, length of stay and property type are some of the things that can determine the price of a holiday home. Simply add your travel dates to find the ultimate escape. From cosy cabins to sprawling luxury villas, all Bookabach holiday homes offer incredible value.

How much does it cost to rent a beach house in Fairlee?

When you travel and the size and style of the property will influence how much you’ll pay for your beachside stay. Enter your Fairlee travel dates to view your available options on Bookabach. Can’t live without a hot tub, or maybe a private pool? Use the filters to select the features and amenities you need.

Are there pet-friendly holiday homes in Fairlee?

Yes. There are. You can pick from five holiday homes that cater to pets in Fairlee. Lots of our pet-friendly holiday homes have a backyard for your furry friend to play in, complimentary treats, doggie beds and proximity to parks and green space. Apply the “Pets allowed” filter to find a holiday home on Bookabach that’s pawfect.

What are popular home amenities in Fairlee?

Some of the most popular home amenities people are looking for in Fairlee are a nearby waterfront, a garden and nearby museums. Whether you’re travelling with family, your besties or even pets, Bookabach holiday homes include the best amenities for starting a new adventure with the people you cherish the most.

Are there holiday homes in Fairlee that welcome kids?

Fairlee has five family-friendly holiday homes to choose from. And discovering a stay that welcomes little ones is simple with our “Properties good for families” filter. Besides having the entire place to yourselves, you’ll also get access to conveniences and perks like multiple bedrooms, kitchens and yards.

What are the top attractions for families in Fairlee?

Keep the kids busy at these fabulous family-friendly attractions in Fairlee:

Historical Society of Kent County Maryland
River Arts Chestertown
Rolphs Wharf Marina

Can I find two-bedroom holiday homes in Fairlee?

Take off with your besties and enjoy total privacy and comfort in one of the two two-bedroom holiday homes Fairlee has to offer.

Are there holiday homes with WiFi in Fairlee?

You’ll have a choice of three holiday homes with WiFi in Fairlee. If you want to disconnect from the world on your break, but still want to be connected to the web, these properties have what you need. Narrow your search by applying the WiFi filter on Bookabach.

How can I find holiday homes with air conditioning in Fairlee?

You’ll find five holiday homes with air conditioning in Fairlee providing that gentle, cool breeze and extra comfort level. Simply enter your preferred dates of travel and then make use of our filters to help you find properties with air conditioning.

How old do you have to be to rent a holiday home in Fairlee?

The minimum required age is normally 16, 18 or 21. It can differ from one property to another on Bookabach, so check the rules of your preferred Fairlee holiday home before booking your escape.

How long can I rent a holiday home in Fairlee for?

It’s down to the Fairlee property. To view a list of options offering extended stays, just enter your dates and guest number into the Bookabach search page. You can look forward to having the property to yourself, along with comforts such as a fully-equipped kitchen and outdoor spaces where the kids can play. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.