Fairlee holiday rentals

We found 120 holiday rentals — enter your dates for availability
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:8 Jan - 15 Jan

Interior
Interior
SuperMoon rising behind the house with moon beams on the bay
Dining
Exceptional
(47 reviews)

Sunset Lodge on the Bay

Rock Hall

9% off
AU$11,589
for 7 nights, 1 home
AU$1,656 per night
includes taxes & fees
Sunset Lodge on the Bay
New playground, with splash pad, at the park within walking distance.
View from the porch. Enjoy ospreys and eagles, sailboats and ships.
Bedroom 1, with desk and window seat.
Picnic pavilion by the beach. There is also a grassy area with charcoal grills.
Exceptional
(61 reviews)

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Betterton

12% off
AU$3,813
for 7 nights, 1 home
AU$545 per night
includes taxes & fees
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Dining
Exterior
Interior
3rd floor suite; queen and 2 twins; en-suite bath, sitting area, deck access.
Exceptional
(5 reviews)

Grand home located right on Main St, walk to Chesapeake Bay & great restaurants

Rock Hall

8% off
AU$8,072
for 7 nights, 1 home
AU$1,153 per night
includes taxes & fees
Grand home located right on Main St, walk to Chesapeake Bay & great restaurants
House front
Front gardens
Property grounds
Interior
Exceptional
(65 reviews)

Beautiful Retreat Located in Rock Hall - walk to everything!

Rock Hall

13% off
AU$3,171
for 7 nights, 1 home
AU$453 per night
includes taxes & fees
Beautiful Retreat Located in Rock Hall - walk to everything!
Property grounds
Outdoor dining
dining area
kitchen
Exceptional
(40 reviews)

This is truly a Baydream!

Rock Hall

8% off
AU$2,996
for 7 nights, 1 home
AU$428 per night
includes taxes & fees
This is truly a Baydream!
Interior
Terrace/patio
Living area
Interior
Exceptional
(9 reviews)

Brand New Modern Rock Hall home with Water Views

Rock Hall

8% off
AU$3,357
for 7 nights, 1 home
AU$480 per night
includes taxes & fees
Brand New Modern Rock Hall home with Water Views
Private kitchen
Exterior
Room
Interior
Exceptional
(11 reviews)

Cute waterfront apartment -- 8 min from the beach!

Rock Hall

8% off
AU$2,430
for 7 nights, 1 apartment
AU$347 per night
includes taxes & fees
Cute waterfront apartment -- 8 min from the beach!
upper floor bedroom with 2 queen beds
living room w Tv and door to porch
Apartment above the Hickory Store
main floor porch
Exceptional
(14 reviews)

Knot's Landing, spacious Apt. downtown Rock Hall

Rock Hall

8% off
AU$2,415
for 7 nights, 1 apartment
AU$345 per night
includes taxes & fees
Knot's Landing, spacious Apt. downtown Rock Hall
Kitchen
Kitchen
Living Room
Family Room
Exceptional
(91 reviews)

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Chestertown

17% off
AU$3,221
for 7 nights, 1 home
AU$460 per night
includes taxes & fees
Circa 1900 Home in the Heart of Historic Downtown Chestertown

  • 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 (16.1 mi / 25.9 km)
  • Cassinelli Winery and Vineyards (11.1 mi / 17.9 km)
  • Crumpton Auction (13.9 mi / 22.3 km)
  • Crow Farm and Vineyard (14.6 mi / 23.5 km)
  • Rocky Point Golf Course (13.1 mi / 21.1 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:

  • 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)
  • Northern Chesapeake Bay (20.1 mi / 32.3 km)
  • Earle Landing (10.1 mi / 16.2 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 best area to stay in Fairlee when booking a holiday rental?
When considering a holiday rental in Fairlee, Maryland, a popular area to stay in is the charming neighbourhood near the waterfront. This area offers a delightful blend of tranquillity and picturesque views, making it an ideal spot for a relaxing getaway. You can find a variety of properties here, ranging from quaint cottages to larger family homes, providing ample options for different group sizes.One of the top attractions nearby is the beautiful Kent Narrows, which is great for water-based activities such as kayaking and boating. The scenic views and vibrant setting add to the charm of the area. Additionally, the nearby Chesapeake Bay Maritime Museum is a fantastic point of interest, offering insights into the region's rich maritime history and culture. Staying in this area not only allows you to enjoy the natural beauty of Fairlee but also provides easy access to local dining and shopping experiences.
What are the top attractions in Fairlee?
In Fairlee, Maryland, visitors can enjoy a range of attractions that highlight the area's natural beauty and outdoor activities. The nearby Chesapeake Bay offers opportunities for boating, fishing, and enjoying the scenic waterfront. The area is also close to the historic town of Chestertown, known for its charming streets, art galleries, and the waterfront park along the Chester River, where you can take leisurely strolls or enjoy local events.For those interested in nature, the Eastern Neck National Wildlife Refuge provides a serene setting for birdwatching and hiking, with trails that showcase the diverse wildlife of the region.
Are all fees included in the Fairlee holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Fairlee holiday homes with parking?
Stayz offers a wide selection of holiday homes in Fairlee with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Fairlee holiday homes?
You can find great discounts on holiday homes in Fairlee on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Fairlee holiday home booking on Stayz?
To find Fairlee holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Fairlee?
A long-stay holiday home in Fairlee is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Fairlee holiday home?
Book your Fairlee holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Fairlee?
Prices for holiday homes in Fairlee vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Fairlee to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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