Maryland holiday lettings

We found 598 holiday rentals — enter your dates for availability
Discover a selection of 44 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:4 Dec - 11 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

16% off
£1,862
for 7 nights, 1 room
£266 per night
includes taxes & fees
RESTORED 1875 FARMHOUSE 1.9 MILES TO DREAMS PARK AND 1.7 MILES TO VILLAGE
Entrance
Interior
Large Gourmet Kitchen ( Dining rooms on each side)
Outdoor dining
Exceptional
(17 reviews)

Bear Lodge

Milford

7% off
£4,421
for 7 nights, 1 room
£632 per night
includes taxes & fees
Bear Lodge
Interior
Outdoor dining
Dining
Private kitchen
Exceptional
(48 reviews)

A Lakeview Paradise

Oneonta

7% off
£4,578
for 7 nights, 1 home
£654 per night
includes taxes & fees
A Lakeview Paradise
Room
Outdoor dining
Exterior
Interior
Exceptional
(16 reviews)

Cooperstown getaway booking 2026!

Cooperstown

8% off
£2,084
for 7 nights, 1 home
£298 per night
includes taxes & fees
Cooperstown getaway booking 2026!
Property grounds
Terrace/patio
Exterior
Dining
Exceptional
(20 reviews)

Lakefront, family friendly home -Baseball campers!

Oneonta

15% off
£1,732
for 7 nights, 1 home
£247 per night
includes taxes & fees
Lakefront, family friendly home -Baseball campers!
Dining room opens onto the kitchen
Fully equipped chef's kitchen, antique work table, exposed beams
Cozy reading area, deck views
Goose down duvets and pillows. Pond views
Exceptional
(10 reviews)

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

Delhi

8% off
£1,663
for 7 nights, 1 home
£238 per night
includes taxes & fees
Idyllic Catskill Retreat-Historic 3 BR 3 Bath Farmhouse, Private Pond, AC, WiFi
Exterior
Exterior
Interior
Second floor, main living area.
Exceptional
(24 reviews)

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

Milford

7% off
£1,894
for 7 nights, 1 home
£271 per night
includes taxes & fees
Private Home 4 miles to Cooperstown, no visible neighbors and close to all.
Exterior
Outdoor dining
Interior
Room
Exceptional
(6 reviews)

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

Milford

8% off
£2,524
for 7 nights, 1 home
£361 per night
includes taxes & fees
Charming 3-bedroom house with a Pool, WiFi, AC 5 minutes from the Dreams Park
Living area
Terrace/patio
Exterior
Private kitchen
Exceptional
(9 reviews)

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

Davenport Center

7% off
£1,442
for 7 nights, 1 home
£206 per night
includes taxes & fees
Fall foliage leaf colors! 3 bd home on gorgeous horse farm, AC, laundry, & views
Private kitchen
Terrace/patio
Interior
Living area
Exceptional
(187 reviews)

Cooperstown Hall of Fame, Dreams Park Baseball, Ommegang #1 Location in the area

Cooperstown

8% off
£1,164
for 7 nights, 1 home
£166 per night
includes taxes & fees
Cooperstown Hall of Fame, Dreams Park Baseball, Ommegang #1 Location in the area
The studio has it's own patio with BBQ that overlooks the front garden.
Guest suite is located on the ground floor of the house.
The living area has good natural light to relax in.
Eat in kitchen area.
Exceptional
(15 reviews)

Cooperstown Modern Studio

Cooperstown

8% off
£1,094
for 7 nights, 1 apartment
£156 per night
includes taxes & fees
Cooperstown Modern Studio

  • 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, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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)
  • Barnyard Swing Miniature Golf (9.2 mi / 14.9 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)

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:

  • Goodyear Lake (5.3 mi / 8.5 km)
  • 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)
  • Canadarago Lake (20.2 mi / 32.5 km)
  • West Davenport Park (7.4 mi / 11.9 km)

Frequently asked questions

How much does it cost to rent a holiday home in Maryland?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Maryland to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Maryland holiday house rentals?
You can find great discounts on house rentals in Maryland on Vrbo, 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.
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.
Can I find long-stay holiday rentals in Maryland?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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 Vrbo.
Are there any Maryland holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
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.
How early should I book a Maryland holiday rental?
Book your Maryland holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my Maryland home rental booking on Vrbo?
To find Maryland holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Maryland holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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