Maryland holiday rentals

We found 589 holiday rentals — enter your dates for availability
Discover a selection of 41 homes and other holiday rentals in Maryland that are perfect for your trip. Holiday rentals offer the best amenities for your family, friends or furry companion, such as air conditioning and Wi-Fi. You're sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Maryland

Showing deals for:18 Dec - 25 Dec

Interior
Private kitchen
Outdoor dining
Interior
Exceptional
(35 reviews)

RESTORED 1875 FARMHOUSE 1.9 MILES TO DREAMS PARK AND 1.7 MILES TO VILLAGE

Cooperstown

17% off
AU$3,424
for 7 nights, 1 room
AU$489 per night
includes taxes & fees
RESTORED 1875 FARMHOUSE 1.9 MILES TO DREAMS PARK AND 1.7 MILES TO VILLAGE
Large Gourmet Kitchen ( Dining rooms on each side)
Interior
Entrance
Room
Exceptional
(17 reviews)

Bear Lodge

Milford

8% off
AU$7,984
for 7 nights, 1 room
AU$1,141 per night
includes taxes & fees
Bear Lodge
Interior
Outdoor dining
Private kitchen
Living area
Exceptional
(48 reviews)

A Lakeview Paradise

Oneonta

8% off
AU$8,270
for 7 nights, 1 home
AU$1,181 per night
includes taxes & fees
A Lakeview Paradise
Miscellaneous
Interior
Property grounds
Kitchen - Electric Stove Microwave, Dishwasher, Toasters, Coffee, Tea.
Exceptional
(64 reviews)

Home for the Holidays in Cooperstown 4BR • Sleeps 14 • 8 Private Acres

Cooperstown

8% off
AU$7,992
for 7 nights, 1 home
AU$1,142 per night
includes taxes & fees
Home for the Holidays in Cooperstown 4BR • Sleeps 14 • 8 Private Acres
Exterior
Outdoor dining
Private kitchen
Room
Exceptional
(17 reviews)

Cooperstown getaway booking 2026!

Cooperstown

8% off
AU$4,311
for 7 nights, 1 home
AU$616 per night
includes taxes & fees
Cooperstown getaway booking 2026!
Exterior
Terrace/patio
Dining
Property grounds
Exceptional
(22 reviews)

Lakefront, family friendly home -Baseball campers!

Oneonta

16% off
AU$3,185
for 7 nights, 1 home
AU$455 per night
includes taxes & fees
Lakefront, family friendly home -Baseball campers!
Goose down duvets and pillows. Pond views
Fully equipped chef's kitchen, antique work table, exposed beams
Master suite, sitting and working areas
Cozy reading area, deck views
Exceptional
(10 reviews)

Idyllic Catskill Retreat-Historic 3 BR 3 Bath Farmhouse, Private Pond, AC, WiFi

Delhi

8% off
AU$3,058
for 7 nights, 1 home
AU$437 per night
includes taxes & fees
Idyllic Catskill Retreat-Historic 3 BR 3 Bath Farmhouse, Private Pond, AC, WiFi
Exterior
Outdoor dining
Interior
Pool
Exceptional
(6 reviews)

Charming 3-bedroom house with a Pool, WiFi, AC 5 minutes from the Dreams Park

Milford

8% off
AU$4,664
for 7 nights, 1 home
AU$666 per night
includes taxes & fees
Charming 3-bedroom house with a Pool, WiFi, AC 5 minutes from the Dreams Park
Exterior
Terrace/patio
Living area
Interior
Exceptional
(9 reviews)

Baseball! Fall foliage! 3 bd home on gorgeous horse farm, AC, laundry, & views

Davenport Center

8% off
AU$2,717
for 7 nights, 1 home
AU$388 per night
includes taxes & fees
Baseball! Fall foliage! 3 bd home on gorgeous horse farm, AC, laundry, & views
Main living area, spiral to ground level.
Exterior
Second floor, main living area.
Interior
Exceptional
(25 reviews)

Private Home 4 miles to Cooperstown, no visible neighbors and close to all.

Milford

7% off
AU$3,464
for 7 nights, 1 home
AU$495 per night
includes taxes & fees
Private Home 4 miles to Cooperstown, no visible neighbors and close to all.
Eat in kitchen area.
Guest suite is located on the ground floor of the house.
The studio has it's own patio with BBQ that overlooks the front garden.
Cooperstown, the National Baseball Hall of Fame and Otsego Lake are 5 minutes.
Exceptional
(15 reviews)

Cooperstown Modern Studio

Cooperstown

8% off
AU$1,659
for 7 nights, 1 apartment
AU$237 per night
includes taxes & fees
Cooperstown Modern Studio

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Why visit Maryland

  • Outdoor Adventures: Maryland offers a range of outdoor activities, from hiking in national parks to exploring scenic trails, perfect for nature enthusiasts.
  • Cultural Heritage: Immerse yourself in the city’s rich history through local museums and arts centres that celebrate Maryland’s unique heritage.
  • Family-Friendly Attractions: The city caters to families with numerous engaging activities and experiences suitable for all ages.
  • Charming Neighbourhoods: Stroll through picturesque streets that reflect the community spirit and local culture of Maryland.
  • Eco-Conscious Experiences: Enjoy eco-friendly travel options and activities that promote sustainability while exploring the city.

Popular types of accommodation in Maryland

Discover Maryland in New York, United States of America, a charming city offering a variety of holiday rentals. Whether it's a cosy private holiday home, an apartment, or a quaint cabin, you'll find comfortable accommodations to suit your needs. Explore local attractions, landmarks, and experiences unique to Maryland, making your stay both enjoyable and memorable. Experience transparency, savings and reassurance with our extensive selection of many holiday home options in this delightful destination.

  • Private Holiday Homes: Experience the comfort and convenience of a fully equipped home, perfect for families or groups seeking a spacious retreat.
  • Apartments: Ideal for couples or solo travellers, these self-contained units offer a blend of privacy and accessibility in vibrant locations.
  • Cabins: Embrace nature with a charming cabin stay, often nestled in serene landscapes, providing a cosy escape.
  • Cottages: Quaint and inviting, cottages offer a delightful rural experience, perfect for a romantic getaway or peaceful retreat.
  • Chalets: Often found in picturesque settings, chalets provide a unique blend of comfort and rustic charm, perfect for a relaxing holiday.**

Top attractions near Maryland

Maryland, New York, offers a remarkable blend of outdoor adventures and cultural experiences. Visitors can explore sports museums, national state parks and arts centres, all set against scenic backdrops. Ideal for family holidays and eco-friendly travel, this city caters to those seeking both active pursuits and a taste of local heritage. Whether you prefer leisurely strolls or engaging in more vigorous activities, Maryland provides a diverse range of attractions to suit every traveller's interests.

  • National Baseball Hall of Fame: This iconic sports museum celebrates the rich history of baseball, showcasing memorabilia and exhibits that capture the essence of America’s pastime. Immerse yourself in the culture and excitement of the sport while exploring the hall's fascinating collections.
  • Rail Explorers Cooperstown: Experience the thrill of riding along scenic railway tracks on custom-designed rail bikes. This unique adventure offers a picturesque journey through the countryside, combining history with a touch of fun and culture.
  • Foothills Performing Arts Center: A vibrant venue for the arts, this centre hosts a variety of performances and events. Enjoy the rich cultural scene through theatre, music, and dance, all in a welcoming community atmosphere.

Things to do recommended for couples

Discover Maryland's charm with a cosy drive through its scenic byways, hand in hand, exploring quaint towns and indulging in intimate dining experiences in hidden gems. Let your spirits soar as you immerse in the local culture.

Things to do recommended for families

Families will delight in Maryland's engaging attractions, from interactive museums to scenic parks, ensuring unforgettable local experiences and treasured moments throughout your visit.

Things to do recommended for groups

Groups visiting Maryland can enjoy a scenic tour of the Chesapeake Bay, indulge in local crab feasts, and explore the historic sites in Annapolis. Engage in team-building activities at the Adventure Park or unwind with wine tasting at local vineyards for a delightful experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Maryland

Whether you're journeying with a group, as a family, with your pets or seeking extended stays, be sure to apply the appropriate filters. Here are some Stayz booking tips to consider.

  • Traveling to Maryland with a group: Consider how many bedrooms you'll require, along with amenities like a fully-equipped kitchen or outdoor area for group get-togethers. Fortunately, on Stayz you can filter for all these features and more.
  • Traveling to Maryland with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, as well as to seek out suitable amenities like a private swimming pool. Additionally, it's wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Maryland: For many, a family holiday is not complete without their four-legged companion. If this resonates with you, then explore Stayz properties that welcome pets. The majority of these pet-friendly accommodations provide feeding bowls and beds, ensuring that everyone feels right at home.
  • Planning for a long term stay visiting Maryland: If you're seeking holiday lets offering discounts for stays of a month or more, you've come to the right place. By utilising the appropriate filters, you can effortlessly locate and save on monthly rentals. You might also want to refine your search by including options such as a parking space, a well-equipped kitchen, or a private pool.

Where to stay near Maryland

Maryland offers a delightful blend of outdoor adventures, family-friendly attractions and eco-conscious experiences. Explore the city’s rich history, scenic neighbourhoods, and vibrant local culture. Discover a variety of family-oriented activities, charming streets, and lush parks that celebrate Maryland’s unique heritage and community spirit. Enjoy an unforgettable holiday immersed in both historical intrigue and natural beauty.

  • Cooperstown: Nestled merely 19km from Maryland, Cooperstown is a charming city celebrated for its outdoor allure, family-friendly atmosphere and eco-conscious spirit. Visitors can explore a variety of venues, ranging from theatres to expansive recreational areas, and enriching educational centres. The city boasts a well-known sports facility stadium, a picturesque park and a serene lake, ensuring a medley of experiences that mix leisure with active pursuits. Its geographic setting makes it an ideal destination for those who appreciate natural landscapes and cultural gatherings.
  • Oneonta: Situated 18km from Maryland, Oneonta offers a vibrant travel experience where sports, outdoor activities and family excursions take centre stage. The city provides numerous opportunities to engage in education, shop in bustling retail areas or enjoy a day on the ski slopes. With attractions including a sports facility stadium, a park and a lake, Oneonta perfectly balances recreational adventures with a rich cultural tapestry, making it a delightful spot for visitors of all ages.
  • Milford: Located only 8km from Maryland, Milford is a delightful city that epitomises an outdoor, family and eco-friendly environment. Travellers can enjoy a range of activities from educational excursions, visits to recreational areas and theatre outings. The local attractions, comprising a sports facility stadium, a park and a lake, enhance its appeal as a compact yet engaging destination. Its proximity to Maryland ensures easy access while offering a distinctive local charm and scenic backdrop.

Best time to go to Maryland

If you're planning a trip to Maryland, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from May to July, while off-peak times, like January and March to April tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January21.4°F (-5.9°C)Light RainVery CloudyLowSlightly Low
February23.4°F (-4.8°C)Light RainVery CloudyAverageAverage
March30.9°F (-0.6°C)Light RainMostly CloudyLowSlightly Low
April42.8°F (6.0°C)Light RainMostly CloudyLowSlightly Low
May55.0°F (12.8°C)Light RainMostly CloudyHighAverage
June62.2°F (16.8°C)Light RainMostly SunnyHighSlightly High
July67.8°F (19.9°C)Light RainMostly SunnyHighSlightly High
August65.8°F (18.8°C)Light RainMostly SunnyAverageSlightly High
September59.4°F (15.2°C)Light RainMostly SunnyAverageAverage
October48.4°F (9.1°C)Light RainMostly CloudyAverageAverage
November36.1°F (2.3°C)Light RainMostly CloudyAverageAverage
December28.4°F (-2.0°C)Light RainMostly CloudyAverageAverage

Booking with Stayz is a breeze

Looking to save on your next break? Consider being flexible with your travel dates, as prices can fluctuate. Booking an extended stay can also lead to substantial savings. To discover the ideal Stayz property that fits your budget, simply use our filters to search by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz's innovative Trip Board offers you a dedicated space to plan new journeys, resume where you last left off, or simply review and organise your travel plans. Previously saved or booked properties are now conveniently categorised under Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.stayz.com.au/trips

**Based on Vrbo properties bookings.

Find the perfect holiday rental for your Maryland getaway

Learn about the unique charm of Maryland with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Maryland

Are you searching for attractions to see while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Maryland a one-of-a-kind holiday spot. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Hobart Book Village (15.5 mi / 25 km)
  • Cooperstown Brewing Company (4.5 mi / 7.3 km)
  • Leatherstocking Golf Course (11.8 mi / 19 km)
  • Stamford Golf Club (15.2 mi / 24.5 km)
  • Otsego Golf Club (19.2 mi / 31 km)
  • Bear Pond Winery (5.5 mi / 8.8 km)

Exploring the natural landscape of Maryland

Whether you're looking for adventure or just want to appreciate the scenery, Maryland is a great place to get outside. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Cooperstown Dreams Park (8.2 mi / 13.2 km)
  • Gilbert Lake State Park (12.8 mi / 20.7 km)
  • Otsego Lake (15.6 mi / 25.1 km)
  • Goodyear Lake (5.3 mi / 8.5 km)
  • Canadarago Lake (20.2 mi / 32.5 km)
  • West Davenport Park (7.4 mi / 11.9 km)

Frequently asked questions

Where are the best Maryland ski resort rentals?
For those seeking ski resort rentals in Maryland, the area around Deep Creek Lake is an excellent choice. This region is home to Wisp Resort, the state's premier ski destination, offering a variety of winter sports activities. Visitors can find a range of accommodations, from cosy cabins to spacious lodges, many of which feature amenities such as fully equipped kitchens, fireplaces, and hot tubs, great for relaxing after a day on the slopes.In the vicinity of Wisp Resort, properties often provide easy access to the ski lifts and offer stunning views of Deep Creek Lake and the surrounding mountains. Many rentals also include outdoor spaces, such as decks or patios, where guests can enjoy the crisp mountain air. Additionally, the area is well-suited for families, with options that include multiple bedrooms and family-friendly amenities.Beyond skiing, the Deep Creek Lake area offers a host of recreational activities, including snow tubing and ice skating in winter, alongside beautiful hiking trails and scenic boat rentals in the warmer months. Visitors can also explore local shops and restaurants in the nearby McHenry and Oakland areas, enhancing their stay with a taste of the local culture and cuisine.
What is the most popular type of holiday rental accomodation in Maryland?
In Maryland, holiday houses are the most popular type of holiday rental, with around 102 available throughout the area. These properties often feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or patios, making them ideal for families and larger groups. Additionally, there are about 12 cottages that provide a charming, rustic experience, typically set in scenic locations near nature trails or waterfront areas. While there are several apartments and chalets available, they are less common compared to the prominent holiday houses.
Are there any family house rentals in Maryland?
In Maryland, there are numerous family-friendly house rentals available, with around 36 options scattered throughout the region. Areas such as Ocean City and the Chesapeake Bay offer inviting homes suitable for families. In Ocean City, properties often feature spacious living areas, fully equipped kitchens for family meals, and outdoor decks or patios, superb for enjoying the coastal breeze after a day at the beach. Many homes provide access to nearby attractions like the boardwalk, amusement parks, and water sports, making them ideal for family outings.Meanwhile, the Chesapeake Bay region boasts larger homes with amenities such as private docks, game rooms, and expansive gardens for children to play in. This area offers a tranquil setting, with opportunities for fishing, boating, and exploring local wildlife. Families can also discover charming towns nearby, where local markets and restaurants serve delicious Maryland crab dishes.
Can I rent a holiday home with a pool or hot tub in Maryland?
In Maryland, there are several holiday homes available for rent that feature pools and hot tubs. This diverse state offers a range of picturesque neighbourhoods where these properties can be found, including the serene Eastern Shore, known for its charming waterfront towns and scenic views, as well as the vibrant areas around Baltimore and Annapolis, which provide both cultural attractions and coastal relaxation.Travellers can expect a variety of amenities in these rentals, such as private pools, inviting hot tubs, and spacious outdoor areas superb for gatherings. Many properties come with fully equipped kitchens, allowing for convenient meal preparation, while others may offer additional features like barbecue grills and cosy lounges, enhancing the overall holiday experience.
Are there pet-friendly house rentals in Maryland?
In Maryland, there are several pet-friendly house rentals available, particularly in areas like Ocean City and the scenic Chesapeake Bay region. In Ocean City, visitors can expect spacious beachfront homes that often come with modern amenities such as fully equipped kitchens, outdoor decks, and sometimes even private pools, making them great for families with pets looking to enjoy the coastal lifestyle.Over in the Chesapeake Bay area, holiday rentals often feature charming cottages or larger homes with access to the water, where you can enjoy activities like kayaking and fishing. Many of these properties provide ample outdoor space, allowing pets to roam freely while their owners relax in the serene surroundings.Additionally, Maryland's state parks and natural reserves, such as Sandy Point State Park, offer beautiful trails and picnic areas that are pet-friendly, creating great opportunities for outdoor adventures.
Are there any remote work holiday rentals in Maryland?
In Maryland, there are numerous remote work holiday rentals available, with around 126 options to choose from. Many properties cater specifically to those looking to combine work and leisure, offering amenities such as high-speed internet, free Wi-Fi, and dedicated workspaces equipped with desk chairs. This makes it easy for remote workers to stay productive while enjoying a change of scenery.Popular areas for these rentals include locations near the Chesapeake Bay, where guests can find charming homes with waterfront views and outdoor spaces for relaxation. Additionally, towns like Annapolis and Frederick offer vibrant local culture and convenient access to cafes and restaurants, great for when it's time to take a break from work. Many rentals also come with comfortable living areas, fully equipped kitchens, and outdoor patios, ensuring a pleasant environment for both work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Maryland?
In Maryland, popular rental amenities include kitchens, which allow guests to prepare their own meals during their stay. Many properties also feature decks or patios, providing outdoor spaces for relaxation or dining al fresco. Additionally, travellers can expect coffee and tea makers in most rentals, great for starting the day with a warm beverage. Onsite parking is commonly available, making it convenient for those travelling by car.
When is the best time to visit Maryland for a holiday rental?
The peak season for visiting Maryland typically spans from May to July, with June being the most popular month for holiday rentals. During this vibrant time, travellers flock to the state to enjoy its rich history, beautiful landscapes, and a variety of outdoor festivals, making it an ideal time for sightseeing and activities.With temperatures ranging from 20 to 30 degrees Celsius in June, the weather is pleasantly warm, great for beach outings and exploring attractions such as the Chesapeake Bay or the historic streets of Annapolis. This comfortable climate encourages visitors to partake in outdoor adventures, from hiking in state parks to enjoying water sports along the coast.For those seeking a more budget-friendly experience, consider planning your visit in March. While this month may be quieter, it offers a unique charm with the early signs of spring, including blooming flowers and fewer crowds. This time is great for enjoying nature walks and the peace of Maryland's picturesque landscapes.
What are the top attractions in Maryland?
In Maryland, New York, visitors can discover a charming small-town atmosphere with several attractions. One of the highlights is the scenic Catskill Park, which offers stunning natural beauty and opportunities for hiking, fishing, and enjoying the outdoors. The nearby Hudson River provides a picturesque backdrop for various recreational activities, including kayaking and boat tours.The town itself features quaint shops and local eateries, making it a pleasant place to explore on foot. For culture enthusiasts, the area hosts art galleries and community events throughout the year, showcasing local talent and craftsmanship.
Are all fees included in the Maryland 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 Maryland holiday homes with parking?
Stayz offers a wide selection of holiday homes in Maryland 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 Maryland holiday homes?
You can find great discounts on holiday homes in Maryland 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 Maryland holiday home booking on Stayz?
To find Maryland 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 Maryland?
A long-stay holiday home in Maryland 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 Maryland holiday home?
Book your Maryland 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 Maryland?
Prices for holiday homes in Maryland 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 Maryland 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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